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This founder was about to shut down his business and open a restaurant. He pivoted the business and grew it to $45m ARR in 12 months. What other businesses can scale like this?
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CountryPitifulThis week

This founder was about to shut down his business and open a restaurant. He pivoted the business and grew it to $45m ARR in 12 months. What other businesses can scale like this?

I heard that Jasper scaled to $45m ARR in 12 months...with a team of 8. For context, they are one of the fastest-growing companies ever. Grew from $0 to $45m ARR in 12 months (then raised $125m at a $1.5b valuation). As a fellow founder, their story is really inspiring to me (curious about what others think): In December 2020, Dave Rogenmoser and his co-founders were on the brink of shutting down their business. They'd spent 3+ years building a conversion optimization software called Proof...and it was flatlining. A few weeks prior they had to make the painful decision to let go of half their team. Competition and churn had completely eroded growth. Things were painful. 8 years of work left them with a string of startups that never quite made it: 2 failed software businesses (couldn't make money*) A SMB marketing agency (maxed out at $25k/mo*) An online course company (hard to get big*) The Pivot: In January 2021, they had an idea to use Chat GPT-3, the generative AI model released 6 months earlier, to write high-converting Facebook ads. Within 30 days, they launched the business. With the skeleton crew remaining from the last startup, they scaled the business to $45m ARR and 70,000+ customers without hiring a single new person. Soon after, they raised $125m at a $1.5b valuation. Dave Rogenmoser, CEO at Jasper, had some great one-liners in a few podcasts I listened to on the business. Here are some of his learnings: Right Skill, Wrong Vehicle: He spent 8 years building marketing businesses which gave this team the knowledge and confidence to spend $1m/mo on sales and marketing to scale the business to $45m ARR in year 1. Launch Fast & Iterate Quickly: The team agreed that if the business didn't work in 30 days, they'd shut it down. Dave says, "If you have been working on a problem for more than 18 months and haven't found Product market fit (PMF), odds are you won't...Make the hard pivot."* Ride A Big Wave: Generative AI technology is a new technology that is changing the way we work. But it's not just text. It's images, voice, etc. Identify new customer segments (e.g., Municipalities, Banks, Lawyers, etc.), learn their problems, and apply this novel technology to solve them. What other businesses have you seen scale like this? I've never seen a SaaS business grow that fast. I meet interesting founders 2x per week and share the learnings here.

This founder was about to shut down his startup and open a restaurant. He pivoted the business and grew it to $45m ARR in 12 months. What else have you seen grow that fast?
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CountryPitifulThis week

This founder was about to shut down his startup and open a restaurant. He pivoted the business and grew it to $45m ARR in 12 months. What else have you seen grow that fast?

I heard that Jasper scaled to $45m ARR in 12 months...with a team of 8. For context, they are one of the fastest-growing companies ever. Grew from $0 to $45m ARR in 12 months (then raised $125m at a $1.5b valuation). As a fellow founder, their story is really inspiring to me (curious about what others think): In December 2020, Dave Rogenmoser and his co-founders were on the brink of shutting down their business. They'd spent 3+ years building a conversion optimization software called Proof...and it was flatlining. A few weeks prior they had to make the painful decision to let go of half their team. Competition and churn had completely eroded growth. Things were painful. 8 years of work left them with a string of startups that never quite made it: 2 failed software businesses (couldn't make money*) A SMB marketing agency (maxed out at $25k/mo*) An online course company (hard to get big*) The Pivot: In January 2021, they had an idea to use Chat GPT-3, the generative AI model released 6 months earlier, to write high-converting Facebook ads. Within 30 days, they launched the business. With the skeleton crew remaining from the last startup, they scaled the business to $45m ARR and 70,000+ customers without hiring a single new person. Soon after, they raised $125m at a $1.5b valuation. Dave Rogenmoser, CEO at Jasper, had some great one-liners in a few podcasts I listened to on the business. Here are some of his learnings: Right Skill, Wrong Vehicle: He spent 8 years building marketing businesses which gave this team the knowledge and confidence to spend $1m/mo on sales and marketing to scale the business to $45m ARR in year 1. Launch Fast & Iterate Quickly: The team agreed that if the business didn't work in 30 days, they'd shut it down. Dave says, "If you have been working on a problem for more than 18 months and haven't found Product market fit (PMF), odds are you won't...Make the hard pivot."* Ride A Big Wave: Generative AI technology is a new technology that is changing the way we work. But it's not just text. It's images, voice, etc. Identify new customer segments (e.g., Municipalities, Banks, Lawyers, etc.), learn their problems, and apply this novel technology to solve them. What other businesses have you seen scale like this? I've never seen a SaaS business grow that fast. I meet interesting founders 2x per week and share the learnings here.

10y of product development, 2 bankruptcies, and 1 Exit — what next? [Extended Story]
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Slight-Explanation29This week

10y of product development, 2 bankruptcies, and 1 Exit — what next? [Extended Story]

10 years of obsessive pursuit from the bottom to impressive product-market fit and exit. Bootstrapping tech products as Software Developer and 3x Startup Founder (2 bankruptcies and 1 exit). Hi everyone, your motivation has inspired me to delve deeper into my story. So, as promised to some of you, I've expanded on it a bit more, along with my brief reflections. There are many founders, product creators, and proactive individuals, I’ve read many of your crazy stories and lessons so I decided to share mine and the lessons I learned from the bottom to impressive product-market fit and exit. I've spent almost the past 10 years building tech products as a Corporate Team Leader, Senior Software Developer, Online Course Creator, Programming Tutor, Head of Development/CTO, and 3x Startup Founder (2 bankruptcies, and 1 exit). And what next? good question... A brief summary of my journey: Chapter 1: Software Developer / Team Leader / Senior Software Developer I’ve always wanted to create products that win over users’ hearts, carry value, and influence users. Ever since my school days, I’ve loved the tech part of building digital products. At the beginning of school, I started hosting servers for games, blogs and internet forums, and other things that did not require much programming knowledge. My classmates and later even over 100 people played on servers that I hosted on my home PC. Later, as the only person in school, I passed the final exam in computer science. During my computer science studies, I started my first job as a software developer. It was crazy, I was spending 200–300 hours a month in the office attending also to daily classes. Yes, I didn’t have a life, but it truly was the fulfillment of my dreams. I was able to earn good money doing what I love, and I devoted fully myself to it. My key to effectively studying IT and growing my knowledge at rocket speed was learning day by day reading guides, building products to the portfolio, watching youtube channels and attending conferences, and even watching them online, even if I didn’t understand everything at the beginning. In one year we’ve been to every possible event within 400km. We were building healthcare products that were actually used in hospitals and medical facilities. It was a beautiful adventure and tons of knowledge I took from this place. That time I built my first product teams, hired many great people, and over the years became a senior developer and team leader. Even I convinced my study mates to apply to this company and we studied together and worked as well. Finally, there were 4 of us, when I left a friend of mine took over my position and still works there. If you’re reading this, I’m sending you a flood of love and appreciation. I joined as the 8th person, and after around 4 years, when I left hungry for change, there were already over 30 of us, now around 100. It was a good time, greetings to everyone. I finished my Master’s and Engineering degrees in Computer Science, and it was time for changes. Chapter 2: 1st time as a Co-founder — Marketplace In the meantime, there was also my first startup (a marketplace) with four of my friends. We all worked on the product, each of us spent thousands of hours, after hours, entire weekends… and I think finally over a year of work. As you might guess, we lacked the most important things: sales, marketing, and product-market fit. We thought users think like us. We all also worked commercially, so the work went very smoothly, but we didn’t know what we should do next with it… Finally, we didn’t have any customers, but you know what, I don’t regret it, a lot of learning things which I used many times later. The first attempts at validating the idea with the market and business activities. In the end, the product was Airbnb-sized. Landing pages, listings, user panels, customer panels, admin site, notifications, caches, queues, load balancing, and much more. We wanted to publish the fully ready product to the market. It was a marketplace, so if you can guess, we had to attract both sides to be valuable. “Marketplace” — You can imagine something like Uber, if you don’t have passengers it was difficult to convince taxi drivers, if you don’t have a large number of taxi drivers you cannot attract passengers. After a year of development, we were overloaded, and without business, marketing, sales knowledge, and budget. Chapter 3: Corp Team Lead / Programming Tutor / Programming Architecture Workshop Leader Working in a corporation, a totally different environment, an international fintech, another learning experience, large products, and workmates who were waiting for 5 pm to finish — it wasn’t for me. Very slow product development, huge hierarchy, being an ant at the bottom, and low impact on the final product. At that time I understood that being a software developer is not anything special and I compared my work to factory worker. Sorry for that. High rates have been pumped only by high demand. Friends of mine from another industry do more difficult things and have a bigger responsibility for lower rates. That’s how the market works. This lower responsibility time allowed for building the first online course after hours, my own course platform, individual teaching newbies programming, and my first huge success — my first B2C customers, and B2B clients for workshops. I pivoted to full focus on sales, marketing, funnels, advertisements, demand, understanding the market, etc. It was 10x easier than startups but allowed me to learn and validate my conceptions and ideas on an easier market and showed me that it’s much easier to locate their problem/need/want and create a service/product that responds to it than to convince people of your innovative ideas. It’s just supply and demand, such a simple and basic statement, in reality, is very deep and difficult to understand without personal experience. If you’re inexperienced and you think you understand, you don’t. To this day, I love to analyze this catchword in relation to various industries / services / products and rediscover it again and again... While writing this sentence, I’m wondering if I’m not obsessed. Chapter 4: Next try — 2nd time as a founder — Edtech Drawing upon my experiences in selling services, offering trainings, and teaching programming, I wanted to broaden my horizons, delve into various fields of knowledge, involve more teachers, and so on. We started with simple services in different fields of knowledge, mainly relying on teaching in the local area (without online lessons). As I had already gathered some knowledge and experience in marketing and sales, things were going well and were moving in the right direction. The number of teachers in various fields was growing, as was the number of students. I don’t remember the exact statistics anymore, but it was another significant achievement that brought me a lot of satisfaction and new experiences. As you know, I’m a technology lover and couldn’t bear to look at manual processes — I wanted to automate everything: lessons, payments, invoices, customer service, etc. That’s when I hired our first developers (if you’re reading this, I’m sending you a flood of love — we spent a lot of time together and I remember it as a very fruitful and great year) and we began the process of tool and automation development. After a year we had really extended tools for students, teachers, franchise owners, etc. We had really big goals, we wanted to climb higher and higher. Maybe I wouldn’t even fully call it Startup, as the client was paying for the lessons, not for the software. But it gave us positive income, bootstrap financing, and tool development for services provided. Scaling this model was not as costless as SaaS because customer satisfaction was mainly on the side of the teacher, not the quality of the product (software). Finally, we grew to nearly 10 people and dozens of teachers, with zero external funding, and almost $50k monthly revenue. We worked very hard, day and night, and by November 2019, we were packed with clients to the brim. And as you know, that’s when the pandemic hit. It turned everything upside down by 180 degrees. Probably no one was ready for it. With a drastic drop in revenues, society started to save. Tired from the previous months, we had to work even harder. We had to reduce the team, change the model, and save what we had built. We stopped the tool’s development and sales, and with the developers, we started supporting other product teams to not fire them in difficult times. The tool worked passively for the next two years, reducing incomes month by month. With a smaller team providing programming services, we had full stability and earned more than relying only on educational services. At the peak of the pandemic, I promised myself that it was the last digital product I built… Never say never… Chapter 5: Time for fintech — Senior Software Developer / Team Lead / Head of Development I worked for small startups and companies. Building products from scratch, having a significant impact on the product, and complete fulfillment. Thousands of hours and sacrifices. This article mainly talks about startups that I built, so I don’t want to list all the companies, products, and applications that I supported as a technology consultant. These were mainly start-ups with a couple of people up to around 100 people on board. Some of the products were just a rescue mission, others were building an entire tech team. I was fully involved in all of them with the hope that we would work together for a long time, but I wasn’t the only one who made mistakes when looking for a product-market fit. One thing I fully understood: You can’t spend 8–15 hours a day writing code, managing a tech team, and still be able to help build an audience. In marketing and sales, you need to be rested and very creative to bring results and achieve further results and goals. If you have too many responsibilities related to technology, it becomes ineffective. I noticed that when I have more free time, more time to think, and more time to bounce the ball against the wall, I come up with really working marketing/sales strategies and solutions. It’s impossible when you are focused on code all day. You must know that this chapter of my life was long and has continued until now. Chapter 6: 3rd time as a founder — sold Never say never… right?\\ It was a time when the crypto market was really high and it was really trending topic. You know that I love technology right? So I cannot miss the blockchain world. I had experience in blockchain topics by learning on my own and from startups where I worked before. I was involved in crypto communities and I noticed a “starving crowd”. People who did things manually and earned money(crypto) on it.I found potential for building a small product that solves a technological problem. I said a few years before that I don’t want to start from scratch. I decided to share my observations and possibilities with my good friend. He said, “If you gonna built it, I’m in”. I couldn’t stop thinking about it. I had thought and planned every aspect of marketing and sales. And you know what. On this huge mindmap “product” was only one block. 90% of the mindmap was focused on marketing and sales. Now, writing this article, I understood what path I went from my first startup to this one. In the first (described earlier) 90% was the product, but in the last one 90% was sales and marketing. Many years later, I did this approach automatically. What has changed in my head over the years and so many mistakes? At that time, the company for which I provided services was acquired. The next day I got a thank you for my hard work and all my accounts were blocked. Life… I was shocked. We were simply replaced by their trusted technology managers. They wanted to get full control. They acted a bit unkindly, but I knew that they had all my knowledge about the product in the documentation, because I’m used to drawing everything so that in the moment of my weakness (illness, whatever) the team could handle it. That’s what solid leaders do, right? After a time, I know that these are normal procedures in financial companies, the point is that under the influence of emotions, do not do anything inappropriate. I quickly forgot about it, that I was brutally fired. All that mattered was to bring my plan to life. And it has been started, 15–20 hours a day every day. You have to believe me, getting back into the game was incredibly satisfying for me. I didn’t even know that I would be so excited. Then we also noticed that someone was starting to think about the same product as me. So the race began a game against time and the market. I assume that if you have reached this point, you are interested in product-market fit, marketing, and sales, so let me explain my assumptions to you: Product: A very very small tool that allowed you to automate proper tracking and creation of on-chain transactions. Literally, the whole app for the user was located on only three subpages. Starving Crowd: We tapped into an underserved market. The crypto market primarily operates via communities on platforms like Discord, Reddit, Twitter, Telegram, and so on. Therefore, our main strategy was directly communicating with users and demonstrating our tool. This was essentially “free marketing” (excluding the time we invested), as we did not need to invest in ads, promotional materials, or convince people about the efficacy of our tool. The community could directly observe on-chain transactions executed by our algorithms, which were processed at an exceptionally fast rate. This was something they couldn’t accomplish manually, so whenever someone conducted transactions using our algorithm, it was immediately noticeable and stirred a curiosity within the community (how did they do that!). Tests: I conducted the initial tests of the application on myself — we had already invested significantly in developing the product, but I preferred risking my own resources over that of the users. I provided the tool access to my wallet, containing 0.3ETH, and went to sleep. Upon waking up, I discovered that the transactions were successful and my wallet had grown to 0.99ETH. My excitement knew no bounds, it felt like a windfall. But, of course, there was a fair chance I could have lost it too. It worked. As we progressed, some users achieved higher results, but it largely hinged on the parameters set by them. As you can surmise, the strategy was simple — buy low, sell high. There was considerable risk involved. Churn: For those versed in marketing, the significance of repeat visitors cannot be overstated. Access to our tool was granted only after email verification and a special technique that I’d prefer to keep confidential. And this was all provided for free. While we had zero followers on social media, we saw an explosion in our email subscriber base and amassed a substantial number of users and advocates. Revenue Generation: Our product quickly gained popularity as we were effectively helping users earn — an undeniable value proposition. Now, it was time to capitalize on our efforts. We introduced a subscription model charging $300 per week or $1,000 per month — seemingly high rates, but the demand was so intense that it wasn’t an issue. Being a subscriber meant you were prioritized in the queue, ensuring you were among the first to reap benefits — thus adding more “value”. Marketing: The quality of our product and its ability to continually engage users contributed to it achieving what can best be described as viral. It was both a source of pride and astonishment to witness users sharing charts and analyses derived from our tool in forum discussions. They weren’t actively promoting our product but rather using screenshots from our application to illustrate certain aspects of the crypto world. By that stage, we had already assembled a team to assist with marketing, and programming, and to provide round-the-clock helpdesk support. Unforgettable Time: Despite the hype, my focus remained steadfast on monitoring our servers, their capacity, and speed. Considering we had only been on the market for a few weeks, we were yet to implement alerts, server scaling, etc. Our active user base spanned from Japan to the West Coast of the United States. Primarily, our application was used daily during the evenings, but considering the variety of time zones, the only time I could afford to sleep was during the evening hours in Far Eastern Europe, where we had the least users. However, someone always needed to be on guard, and as such, my phone was constantly by my side. After all, we couldn’t afford to let our users down. We found ourselves working 20 hours a day, catering to thousands of users, enduring physical fatigue, engaging in talks with VCs, and participating in conferences. Sudden Downturn: Our pinnacle was abruptly interrupted by the war in Ukraine (next macroeconomic shot straight in the face, lucky guy), a precipitous drop in cryptocurrency value, and swiftly emerging competition. By this time, there were 5–8 comparable tools had infiltrated the market. It was a challenging period as we continually stumbled upon new rivals. They immediately embarked on swift fundraising endeavors — a strategy we overlooked, which in retrospect was a mistake. Although our product was superior, the competitors’ rapid advancement and our insufficient funds for expeditious scaling posed significant challenges. Nonetheless, we made a good decision. We sold the product (exit) to competitors. The revenue from “exit” compensated for all the losses, leaving us with enough rest. We were a small team without substantial budgets for rapid development, and the risk of forming new teams without money to survive for more than 1–2 months was irresponsible. You have to believe me that this decision consumed us sleepless nights. Finally, we sold it. They turned off our app but took algorithms and users. Whether you believe it or not, after several months of toiling day and night, experiencing burnout, growing weary of the topic, and gaining an extra 15 kg in weight, we finally found our freedom… The exit wasn’t incredibly profitable, but we knew they had outdone us. The exit covered all our expenses and granted us a well-deserved rest for the subsequent quarter. It was an insane ride. Despite the uncertainty, stress, struggles, and sleepless nights, the story and experience will remain etched in my memory for the rest of my life. Swift Takeaways: Comprehending User Needs: Do you fully understand the product-market fit? Is your offering just an accessory or does it truly satisfy the user’s needs? The Power of Viral Marketing: Take inspiration from giants like Snapchat, ChatGPT, and Clubhouse. While your product might not attain the same scale (but remember, never say never…), the closer your concept is to theirs, the easier your journey will be. If your user is motivated to text a friend saying, “Hey, check out how cool this is” (like sharing ChatGPT), then you’re on the best track. Really. Even if it doesn’t seem immediately evident, there could be a way to incorporate this into your product. Keep looking until you find it. Niche targeting — the more specific and tailored your product is to a certain audience, the easier your journey will be People love buying from people — establishing a personal brand and associating yourself with the product can make things easier. Value: Seek to understand why users engage with your product and keep returning. The more specific and critical the issue you’re aiming to solve, the easier your path will be. Consider your offerings in terms of products and services and focus on sales and marketing, regardless of personal sentiments. These are just a few points, I plan to elaborate on all of them in a separate article. Many products undergo years of development in search of market fit, refining the user experience, and more. And guess what? There’s absolutely nothing wrong with that. Each product and market follows its own rules. Many startups have extensive histories before they finally make their mark (for instance, OpenAI). This entire journey spanned maybe 6–8 months. I grasped and capitalized on the opportunity, but we understood from the start that establishing a startup carried a significant risk, and our crypto product was 10 times riskier. Was it worth it? Given my passion for product development — absolutely. Was it profitable? — No, considering the hours spent — we lose. Did it provide a stable, problem-free life — nope. Did this entire adventure offer a wealth of happiness, joy, and unforgettable experiences — definitely yes. One thing is certain — we’ve amassed substantial experience and it’s not over yet :) So, what lies ahead? Chapter 7: Reverting to the contractor, developing a product for a crypto StartupReturning to the past, we continue our journey… I had invested substantial time and passion into the tech rescue mission product. I came on board as the technical Team Leader of a startup that had garnered over $20M in seed round funding, affiliated with the realm of cryptocurrencies. The investors were individuals with extensive backgrounds in the crypto world. My role was primarily technical, and there was an abundance of work to tackle. I was fully immersed, and genuinely devoted to the role. I was striving for excellence, knowing that if we secured another round of financing, the startup would accelerate rapidly. As for the product and marketing, I was more of an observer. After all, there were marketing professionals with decades of experience on board. These were individuals recruited from large crypto-related firms. I had faith in them, kept an eye on their actions, and focused on my own responsibilities. However, the reality was far from satisfactory. On the last day, the principal investor for the Series A round withdrew. The board made the tough decision to shut down. It was a period of intense observation and gaining experience in product management. This was a very brief summary of the last 10 years. And what next? (Last) Chapter 8: To be announced — Product Owner / Product Consultant / Strategist / CTO After spending countless hours and days deliberating my next steps, one thing is clear: My aspiration is to continue traversing the path of software product development, with the hopeful anticipation that one day, I might ride the crest of the next big wave and ascend to the prestigious status of a unicorn company. I find myself drawn to the process of building products, exploring product-market fit, strategizing, engaging in software development, seeking out new opportunities, networking, attending conferences, and continuously challenging myself by understanding the market and its competitive landscape. Product Owner / Product Consultant / CTO / COO: I’m not entirely sure how to categorize this role, as I anticipate that it will largely depend on the product to which I will commit myself fully. My idea is to find one startup/company that wants to build a product / or already has a product, want to speed up, or simply doesn’t know what’s next. Alternatively, I could be a part of an established company with a rich business history, which intends to invest in digitization and technological advancements. The goal would be to enrich their customer experience by offering complementary digital products Rather than initiating a new venture from ground zero with the same team, I am receptive to new challenges. I am confident that my past experiences will prove highly beneficial for the founders of promising, burgeoning startups that already possess a product, or are in the initial phases of development. ‘Consultant’ — I reckon we interpret this term differently. My aim is to be completely absorbed in a single product, crafting funnels, niches, strategies, and all that is necessary to repeatedly achieve the ‘product-market fit’ and significant revenue. To me, ‘consultant’ resonates more akin to freelancing than being an employee. My current goal is to kickstart as a consultant and aide, dealing with facilitating startups in their journey from point A to B. Here are two theoretical scenarios to illustrate my approach: Scenario 1: (Starting from point A) You have a product but struggle with marketing, adoption, software, strategy, sales, fundraising, or something else. I conduct an analysis and develop a strategy to reach point B. I take on the “dirty work” and implement necessary changes, including potential pivots or shifts (going all-in) to guide the product to point B. The goal is to reach point B, which could involve achieving a higher valuation, expanding the user base, increasing sales, or generating monthly revenue, among other metrics. Scenario 2: (Starting from point A) You have a plan or idea but face challenges with marketing, adoption, strategy, software, sales, fundraising, or something else. I analyze the situation and devise a strategy to reach point B. I tackle the necessary tasks, build the team, and overcome obstacles to propel the product to point B. I have come across the view that finding the elusive product-market fit is the job of the founder, and it’s hard for me to disagree. However, I believe that my support and experiences can help save money, many failures, and most importantly, time. I have spent a great deal of time learning from my mistakes, enduring failure after failure, and even had no one to ask for support or opinion, which is why I offer my help. Saving even a couple of years, realistically speaking, seems like a value I’m eager to provide… I invite you to share your thoughts and insights on these scenarios :) Closing Remarks: I appreciate your time and effort in reaching this point. This has been my journey, and I wouldn’t change it for the world. I had an extraordinary adventure, and now I’m ready for the next exciting battle with the market and new software products. While my entire narrative is centered around startups, especially the ones I personally built, I’m planning to share more insights drawn from all of my experiences, not just those as a co-founder. If you’re currently developing your product or even just considering the idea, I urge you to reach out to me. Perhaps together, we can create something monumental :) Thank you for your time and insights. I eagerly look forward to engaging in discussions and hearing your viewpoints. Please remember to like and subscribe. Nothing motivates to write more than positive feedback :) Matt.

Started a content marketing agency 6 years ago - $0 to $5,974,324 (2023 update)
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mr_t_forhireThis week

Started a content marketing agency 6 years ago - $0 to $5,974,324 (2023 update)

Hey friends, My name is Tyler and for the past 6 years, I’ve been documenting my experience building a content marketing agency called Optimist. Year 1 - 0 to $500k ARR Year 2 - $500k to $1MM ARR Year 3 - $1MM ARR to $1.5MM(ish) ARR Year 4 - $3,333,686 Revenue Year 5 - $4,539,659 Revenue How Optimist Works First, an overview/recap of the Optimist business model: We operate as a “collective” of full time/professional freelancers Everyone aside from me is a contractor Entirely remote/distributed team Each freelancer earns $65-85/hour Clients pay us a flat monthly fee for full-service content marketing (research, strategy, writing, editing, design/photography, reporting and analytics, targeted linkbuilding, and more) We recently introduced hourly engagements for clients who fit our model but have some existing in-house support Packages range in price from $10-20k/mo We offer profit share to everyone on our core team as a way to give everyone ownership in the company In 2022, we posted $1,434,665 in revenue. It was our highest revenue year to date and brings our lifetime total to $5,974,324. Here’s our monthly revenue from January 2017 to December of 2022. But, like every year, it was a mix of ups and downs. Here’s my dispatch for 2023. — Running a business is like spilling a drink. It starts as a small and simple thing. But, if you don’t clean it up, the spill will spread and grow — taking up more space, seeping into every crack. There’s always something you could be doing. Marketing you could be working on. Pitches you could be making. Networking you could be doing. Client work you could help with. It can be all-consuming. And it will be — if you don’t clean up the spill. I realized this year that I had no containment for the spill that I created. Running an agency was spilling over into nearly every moment of my life. When I wasn’t working, I was thinking about work. When I wasn’t thinking about work, I was dreaming about it. Over the years, I’ve shared about a lot of my personal feelings and experience as an entrepreneur. And I also discussed my reckoning with the limitations of running the business we’ve built. My acceptance that it was an airplane but not a rocket. And my plan to try to compartmentalize the agency to make room in my life for other things — new business ideas, new revenue streams, and maybe some non-income-producing activity. 🤷 What I found in 2022 was that the business wasn’t quite ready for me to make that move. It was still sucking up too much of my time and attention. There were still too many gaps to fill and I was the one who was often filling them. So what do you do? Ultimately you have two choices on the table anytime you run a business and it’s not going the way you want it: Walk away Turn the ship — slowly For a huge number of reasons (personal, professional, financial, etc), walking away from Optimist was not really even an option or the right move for me. But it did feel like things needed to change. I needed to keep turning the ship to get it to the place where it fit into my life — instead of my life fitting around the business. This means 2022 was a year of transition for the agency. (Again?) Refocusing on Profit Some money is better than no money. Right? Oddly, this was one of the questions I found myself asking in 2022. Over the years, we’ve been fortunate to have many clients who have stuck with us a long time. In some cases, we’ve had clients work with us for 2, 3, or even 4 years. (That’s over half of our existence!) But, things have gotten more expensive — we’ve all felt it. We’ve had to increase pay to remain competitive for top talent. Software costs have gone up. It’s eaten into our margin. Because of our increasing costs and evolving scope, many of our best, most loyal clients were our least profitable. In fact, many were barely profitable — if at all. We’ve tried to combat that by increasing rates on new, incoming clients to reflect our new costs and try to make up for shrinking margin on long-term clients. But we didn’t have a good strategy in place for updating pricing for current clients. And it bit us in the ass. Subsidizing lower-profit, long-term clients with new, higher-margin clients ultimately didn’t work out. Our margins continued to dwindle and some months we were barely breaking even while posting six-figures of monthly revenue. 2022 was our highest revenue year but one of our least profitable. It only left one option. We had to raise rates on some of our long-term clients. But, of course, raising rates on a great, long-term client can be delicate. You’ve built a relationship with these people over the years and you’re setting yourself up for an ultimatum — are you more valuable to the client or is the client more valuable to you? Who will blink first? We offered all of these clients the opportunity to move to updated pricing. Unfortunately, some of them weren’t on board. Again, we had 2 options: Keep them at a low/no profit rate Let them churn It seems intuitive that having a low-profit client is better than having no client. But we’ve learned an important lesson many times over the years. Our business doesn’t scale infinitely and we can only handle so many clients at a time. That means that low-profit clients are actually costing us money in some cases. Say our average client generates $2,500 per month in profit — $30,000 per year. If one of our clients is only generating $500/mo in profit, working with them means missing out on bringing on a more profitable client (assuming our team is currently at capacity). Instead of $30,000/year, we’re only making $6,000. Keeping that client costs us $24,000. That’s called opportunity cost. So it’s clear: We had to let these clients churn. We decided to churn about 25% of our existing clients. On paper, the math made sense. And we had a pretty consistent flow of new opportunities coming our way. At the time, it felt like a no-brainer decision. And I felt confident that we could quickly replace these low-profit clients with higher-margin ones. I was wrong. Eating Shit Right after we initiated proactively churning some of our clients, other clients — ones we planned to keep — gave us notice that they were planning to end the engagement. Ouch. Fuck. We went from a 25% planned drop in revenue to a nearly 40% cliff staring us right in the face. Then things got even worse. Around Q3 of this year, talk of recession and layoffs really started to intensify. We work primarily with tech companies and startups. And these were the areas most heavily impacted by the economic news. Venture funding was drying up. Our leads started to slow down. This put us in a tough position. Looking back now, I think it’s clear that I made the wrong decision. We went about this process in the wrong way. The reality sinks in when you consider the imbalance between losing a client and gaining a client. It takes 30 days for someone to fire us. It’s a light switch. But it could take 1-3 months to qualify, close, and onboard a new client. We have lots of upfront work, research, and planning that goes into the process. We have to learn a new brand voice, tone, and style. It’s a marathon. So, for every client we “trade”, there’s a lapse in revenue and work. This means that, in retrospect, I would probably have made this transition using some kind of staggered schedule rather than a cut-and-dry approach. We could have gradually off-boarded clients when we had more definitive work to replace them. I was too confident. But that’s a lesson I had to learn the hard way. Rebuilding & Resetting Most of the voluntary and involuntary churn happened toward the end of 2022. So we’re still dealing with the fall out. Right now, it feels like a period of rebuilding. We didn’t quite lose 50% of our revenue, but we definitely saw a big hit heading into 2023. To be transparent: It sucks. It feels like a gigantic mistake that I made which set us back significantly from our previous high point. I acted rashly and it cost us a lot of money — at least on the surface. But I remind myself of the situation we were in previously. Nearly twice the revenue but struggling to maintain profitability. Would it have been better to try to slowly fix that situation and battle through months of loss or barely-break-even profits? Or was ripping off the bandaid the right move after all? I’m an optimist. (Heh, heh) Plus, I know that spiraling over past decisions won’t change them or help me move forward. So I’m choosing to look at this as an opportunity — to rebuild, reset, and refocus the company. I get to take all of the tough lessons I’ve learned over the last 6 years and apply them to build the company in a way that better aligns with our new and current goals. It’s not quite a fresh, clean start, but by parting ways with some of our oldest clients, we’ve eliminated some of the “debt” that’s accumulated over the years. We get a chance to fully realize the new positioning that we rolled out last year. Many of those long-term clients who churned had a scope of work or engagement structure that didn’t fit with our new positioning and focus. So, by losing them, we’re able to completely close up shop on the SOWs that no longer align with the future version of Optimist. Our smaller roster of clients is a better fit for that future. My job is to protect that positioning by ensuring that while we’re rebuilding our new roster of clients we don’t get desperate. We maintain the qualifications we set out for future clients and only take on work that fits. How’s that for seeing the upside? Some other upside from the situation is that we got an opportunity to ask for candid feedback from clients who were leaving. We asked for insight about their decision, what factors they considered, how they perceived us, and the value of our work. Some of the reasons clients left were obvious and possibly unavoidable. Things like budget cuts, insourcing, and uncertainty about the economy all played at least some part of these decisions. But, reading between the lines, where was one key insight that really struck me. It’s one of those, “oh, yeah — duh — I already knew that,” things that can be difficult to learn and easy to forget…. We’re in the Relationship Business (Plan Accordingly) For all of our focus on things like rankings, keywords, content, conversions, and a buffet of relevant metrics, it can be easy to lose the forest for the trees. Yes, the work itself matters. Yes, the outcomes — the metrics — matter. But sometimes the relationship matters more. When you’re running an agency, you can live or die by someone just liking you. Admittedly, this feels totally unfair. It opens up all kinds of dilemmas, frustration, opportunity for bias and prejudice, and other general messiness. But it’s the real world. If a client doesn’t enjoy working with us — even if for purely personal reasons — they could easily have the power to end of engagement, regardless of how well we did our actual job. We found some evidence of this in the offboarding conversations we had with clients. In some cases, we had clients who we had driven triple- and quadruple-digital growth. Our work was clearly moving the needle and generating positive ROI and we had the data to prove it. But they decided to “take things in another direction” regardless. And when we asked about why they made the decision, it was clear that it was more about the working relationship than anything we could have improved about the service itself. The inverse is also often true. Our best clients have lasting relationships with our team. The work is important — and they want results. But even if things aren’t quite going according to plan, they’re patient and quick to forgive. Those relationships feel solid — unshakeable. Many of these folks move onto new roles or new companies and quickly look for an opportunity to work with us again. On both sides, relationships are often more important than the work itself. We’ve already established that we’re not building a business that will scale in a massive way. Optimist will always be a small, boutique service firm. We don’t need 100 new leads per month We need a small, steady roster of clients who are a great fit for the work we do and the value we create. We want them to stick around. We want to be their long-term partner. I’m not built for churn-and-burn agency life. And neither is the business. When I look at things through this lens, I realize how much I can cut from our overall business strategy. We don’t need an ultra-sophisticated, multi-channel marketing strategy. We just need strong relationships — enough of them to make our business work. There are a few key things we can take away from this as a matter of business strategy: Put most of our effort into building and strengthening relationships with our existing clients Be intentional about establishing a strong relationship with new clients as part of onboarding Focus on relationships as the main driver of future business development Embracing Reality: Theory vs Practice Okay, so with the big learnings out the way, I want to pivot into another key lesson from 2022. It’s the importance of understanding theory vs practice — specifically when it comes to thinking about time, work, and life. It all started when I was considering how to best structure my days and weeks around running Optimist, my other ventures, and my life goals outside of work. Over the years, I’ve dabbled in many different ways to block time and find focus — to compartmentalize all of the things that are spinning and need my attention. As I mapped this out, I realized that I often tried to spread myself too thin throughout the week. Not just that I was trying to do too much but that I was spreading that work into too many small chunks rather than carving out time for focus. In theory, 5 hours is 5 hours. If you have 5 hours of work to get done, you just fit into your schedule whenever you have an open time slot. In reality, a single 5-hour block of work is 10x more productive and satisfying than 10, 30-minute blocks of work spread out across the week. In part, this is because of context switching. Turning your focus from one thing to another thing takes time. Achieving flow and focus takes time. And the more you jump from one project to another, the more time you “lose” to switching. This is insightful for me both in the context of work and planning my day, but also thinking about my life outside of Optimist. One of my personal goals is to put a finite limit on my work time and give myself more freedom. I can structure that in many different ways. Is it better to work 5 days a week but log off 1 hour early each day? Or should I try to fit more hours into each workday so I can take a full day off? Of course, it’s the latter. Both because of the cost of context switching and spreading work into more, smaller chunks — but also because of the remainder that I end up with when I’m done working. A single extra hour in my day probably means nothing. Maybe I can binge-watch one more episode of a new show or do a few extra chores around the house. But it doesn’t significantly improve my life or help me find greater balance. Most things I want to do outside of work can’t fit into a single extra hour. A full day off from work unlocks many more options. I can take the day to go hiking or biking. I can spend the day with my wife, planning or playing a game. Or I can push it up against the weekend and take a 3-day trip. It gives me more of the freedom and balance that I ultimately want. So this has become a guiding principle for how I structure my schedule. I want to: Minimize context switching Maximize focused time for work and for non-work The idea of embracing reality also bleeds into some of the shifts in business strategy that I mentioned above. In theory, any time spent on marketing will have a positive impact on the company. In reality, focusing more on relationships than blasting tweets into the ether is much more likely to drive the kind of growth and stability that we’re seeking. As I think about 2023, I think this is a recurring theme. It manifests in many ways. Companies are making budget cuts and tough decisions about focus and strategy. Most of us are looking for ways to rein in the excess and have greater impact with a bit less time and money. We can’t do everything. We can’t even do most things. So our #1 priority should be to understand the reality of our time and our effort to make the most of every moment (in both work and leisure). That means thinking deeply about our strengths and our limitations. Being practical, even if it feels like sacrifice. Update on Other Businesses Finally, I want to close up by sharing a bit about my ventures outside of Optimist. I shared last year how I planned to shift some of my (finite) time and attention to new ventures and opportunities. And, while I didn’t get to devote as much as I hoped to these new pursuits, they weren’t totally in vain. I made progress across the board on all of the items I laid out in my post. Here’s what happened: Juice: The first Optimist spin-out agency At the end of 2021, we launched our first new service business based on demand from Optimist clients. Focused entirely on building links for SEO, we called the agency Juice. Overall, we made strong progress toward turning this into a legitimate standalone business in 2022. Relying mostly on existing Optimist clients and a few word-of-mouth opportunities (no other marketing), we built a team and set up a decent workflow and operations. There’s still many kinks and challenges that we’re working through on this front. All told, Juice posted almost $100,000 in revenue in our first full year. Monetizing the community I started 2022 with a focus on figuring out how to monetize our free community, Top of the Funnel. Originally, my plan was to sell sponsorships as the main revenue driver. And that option is still on the table. But, this year, I pivoted to selling paid content and subscriptions. We launched a paid tier for content and SEO entrepreneurs where I share more of my lessons, workflows, and ideas for building and running a freelance or agency business. It’s gained some initial traction — we reached \~$1,000 MRR from paid subscriptions. In total, our community revenue for 2022 was about $2,500. In 2023, I’m hoping to turn this into a $30,000 - $50,000 revenue opportunity. Right now, we’re on track for \~$15,000. Agency partnerships and referrals In 2022, we also got more serious about referring leads to other agencies. Any opportunity that was not a fit for Optimist or we didn’t have capacity to take on, we’d try to connect with another partner. Transparently, we struggled to operationalize this as effectively as I would have liked. In part, this was driven by my lack of focus here. With the other challenges throughout the year, I wasn’t able to dedicate as much time as I’d like to setting goals and putting workflows into place. But it wasn’t a total bust. We referred out several dozen potential clients to partner agencies. Of those, a handful ended up converting into sales — and referral commission. In total, we generated about $10,000 in revenue from referrals. I still see this as a huge opportunity for us to unlock in 2023. Affiliate websites Lastly, I mentioned spending some time on my new and existing affiliate sites as another big business opportunity in 2022. This ultimately fell to the bottom of my list and didn’t get nearly the attention I wanted. But I did get a chance to spend a few weeks throughout the year building this income stream. For 2022, I generated just under $2,000 in revenue from affiliate content. My wife has graciously agreed to dedicate some of her time and talent to these projects. So, for 2023, I think this will become a bit of a family venture. I’m hoping to build a solid and consistent workflow, expand the team, and develop a more solid business strategy. Postscript — AI, SEO, OMG As I’m writing this, much of my world is in upheaval. If you’re not in this space (and/or have possibly been living under a rock), the release of ChatGPT in late 2022 has sparked an arms race between Google, Bing, OpenAI, and many other players. The short overview: AI is likely to fundamentally change the way internet search works. This has huge impact on almost all of the work that I do and the businesses that I run. Much of our focus is on SEO and understanding the current Google algorithm, how to generate traffic for clients, and how to drive traffic to our sites and projects. That may all change — very rapidly. This means we’re standing at a very interesting point in time. On the one hand, it’s scary as hell. There’s a non-zero chance that this will fundamentally shift — possibly upturn — our core business model at Optimist. It could dramatically change how we work and/or reduce demand for our core services. No bueno. But it’s also an opportunity (there’s the optimist in me, again). I certainly see a world where we can become leaders in this new frontier. We can pivot, adjust, and capitalize on a now-unknown version of SEO that’s focused on understanding and optimizing for AI-as-search. With that, we may also be able to help others — say, those in our community? — also navigate this tumultuous time. See? It’s an opportunity. I wish I had the answers right now. But, it’s still a time of uncertainty. I just know that there’s a lot of change happening and I want to be in front of it rather than trying to play catch up. Wish me luck. — Alright friends — that's my update for 2023! I’ve always appreciated sharing these updates with the Reddit community, getting feedback, being asked tough questions, and even battling it out with some of my haters (hey!! 👋) As usual, I’m going to pop in throughout the next few days to respond to comments or answer questions. Feel free to share thoughts, ideas, and brutal takedowns in the comments. If you're interested in following the Optimist journey and the other projects I'm working on in 2023, you can follow me on Twitter. Cheers, Tyler P.S. - If you're running or launching a freelance or agency business and looking for help figuring it out, please DM me. Our subscription community, Middle of the Funnel, was created to provide feedback, lessons, and resources for other entrepreneurs in this space.

My boss taught me how to build a Failed business (15 lessons)
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aminekhThis week

My boss taught me how to build a Failed business (15 lessons)

I'm a senior software developer at a three-year-old startup that has been making $0 in revenue. I've been with this startup since its beginning, and it pays me $1200/month. My boss has broken the records of the number of stupid ideas and stupid features that he asked me to implement. He taught me (unintentionally) all the lessons I should NOT do to build a successful business. From bad product ideas, bad business decisions, not listening to your team, not building what target customers want, and falling in love with your bad product. The product we're working on is a desktop program that moves the cursor with your finger using the webcam (gesture recognition). Why in the world would anyone pay money to move the mouse cursor with his finger? No one knows. My boss watched Iron Man (the film) and saw how Tony Starks do gestures in front of his "advanced" computer and thought it was cool so he asked me to build this for him to sell it to enterprises (then pivoted the target customer to schools). Of course, no one bought this software. All the people he meets tell him it is cool but he never hears from them again. No one on the team, except my boss, thinks this software will succeed. He keeps adding irrelevant features to this software just because he "thinks" people will love it. We added 3D object visualizer, ChatGPT integration, and Quizzes. I suggested moving everything to the cloud and focusing only on improving the education industry by providing solutions that help teachers better prepare their lessons and understand where each student lacks by recording lessons, summarizing them for students, generating quizzes using AI, and analyzing the part that each student didn't understand. However, to do that, we need to forget the part of moving the cursor with fingers because it can be done only on Python, not NextJS. He simply replied, "NO, moving the cursor with fingers is COOL". So here are the lessons I learned from my boss to build a failed business: Never listen to your team. Always build what you think is good and never let anyone from your team say it's a bad idea. Fall in love with your business idea. Don't talk to customers. If no one bought your product, it's because they don't understand how cool it is. If a member of your team say it's a bad idea, ignore them, they don't understand how cool your idea is. Always hire interns because they're free labor and give them the most sensitive parts of the work like payments and databases. Make your business dependant on you. Don't let your team do their job the right way, give them orders to do it YOUR way. Hire experts to tell them what to do not to tell you what to do and how to do it. Never do marketing because people will steal your idea. Ask your team "What you think?" but ignore them. If your wife and children think your product is cool then it's cool. Start a business in an industry that you know nothing about but act like you know everything. If no one is buying your product, keep adding irrelevant features that no one asked for. \--- Edit: I didn't mention all the "stupid" ideas I built for him so here you go: Replacing Zoom, Teams, and Meet meetings with meetings in the metaverse. Target customer: Enterprises. An app that lets you scroll through social media without touching your mobile screen (using gesture recognition). We didn't build this because it's technically impossible to continuously use the phone camera outside your own app. He didn't believe me so asked his friend and told him the same thing. A software that controls the computer with gestures (moving cursor, single click, double click, ALT Tab...). Target customers: Enterprises Building a classroom in Decentraland (metaverse) to replace classes through Zoom and Teams He told me to build the startup website but to not make the home page the first page a user lands on when he opens the website. He wants to make the visitor lands on another "almost" empty page and if the user wants to go to the home page he should click on "Home" in the navbar.

Started a content marketing agency 8 years ago - $0 to $7,863,052 (2025 update)
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mr_t_forhireThis week

Started a content marketing agency 8 years ago - $0 to $7,863,052 (2025 update)

Hey friends, My name is Tyler and for the past 8 years, I’ve been documenting my experience building a content marketing agency called Optimist. Year 1 — 0 to $500k ARR Year 2 — $500k to $1MM ARR Year 3 — $1MM ARR to $1.5MM(ish) ARR Year 4 — $3,333,686 Revenue Year 5 — $4,539,659 Revenue Year 6 — $5,974,324 Revenue Year 7 - $6,815,503 Revenue (Edit: Seems like links are banned now. You can check my post history for all of my previous updates with lessons and learnings.) How Optimist Works First, an overview/recap of the Optimist business model: We operate as a “collective” of full time/professional freelancers Everyone aside from me is a contractor Entirely remote/distributed team We pay freelancers a flat fee for most work, working out to roughly $65-100/hour. Clients pay us a flat monthly fee for full-service content marketing (research, strategy, writing, editing, design/photography, reporting and analytics, targeted linkbuilding, and more)\ Packages range in price from \~$10-20k/mo \This is something we are revisiting now* The Financials In 2024, we posted $1,032,035.34 in revenue. This brings our lifetime revenue to $7,863,052. Here’s our monthly revenue from January 2017 to December of 2024. (Edit: Seems like I'm not allowed to link to the chart.) The good news: Revenue is up 23% YoY. EBITDA in Q4 trending up 1-2 points. We hosted our first retreat in 4 years, going to Ireland with about half the team. The bad news: Our revenue is still historically low. At $1MM for the year, we’re down about 33% from our previous years over $1.5MM. Revenue has been rocky. It doesn’t feel like we’ve really “recovered” from the bumps last year. The trend doesn’t really look great. Even though, anecdotally, it feels like we are moving in a good direction. EBITDA is still hovering at around 7%. Would love to get that closer to 20%. (For those who may ask: I’m calculating EBITDA after paying taxes and W2 portion of my income.) — Almost every year, my update starts the same way: This has been a year of growth and change. Both for my business—and me personally. 2024 was no different. I guess that tells you something about entrepreneurship. It’s a lot more like sailing a ship than driving a car. You’re constantly adapting, tides are shifting, and any blip of calm is usually just a moment before the next storm. As with past years, there’s a lot to unpack from the last 12 months. Here we go again. Everything is Burning In the last 2 years, everything has turned upside down in the world of content and SEO. Back in 2020, we made a big decision to re-position the agency. (See post history) We decided to narrow our focus to our most successful, profitable, and consistent segment of clients and re-work our entire operation to focus on serving them. We defined our ICP as: \~Series A ($10mm+ funding) with 6-12 months runway to scale organic as a channel Product-led company with “simple” sales cycle involving fewer stakeholders Demonstrable opportunity to use SEO to drive business growth Our services: Content focused on growing organic search (SEO) Full-service engagements that included research, planning, writing, design, reporting And our engagement structure: Engaged directly with an executive; ownership over strategy and day-to-day execution 1-2 points of contact or stakeholders Strategic partner that drives business growth (not a service vendor who makes content) Most importantly, we decided that we were no longer going to offer a broader range of content that we used to sell. That included everything from thought leadership content to case studies and ebooks. We doubled-down on “SEO content” for product-led SaaS companies. And this worked phenomenally for us. We started bringing on more clients than ever. We developed a lot of internal system and processes that helped us scale and take on more work than we’ve ever had and drive great outcomes for our ideal clients. But in 2023 and 2024, things started going awry. One big change, of course, was the rise of AI. Many companies and executives (and writers) feel that AI can write content just as well as an agency like ours. That made it a lot harder to sell a $10,000 per month engagement when they feel like the bulk of the work could be “done for free.” (Lots of thoughts on this if you want my opinions.) But it wasn’t just that. Google also started tinkering with their algorithm, introducing new features like AI Overviews, and generally changing the rules of the game. This created 3 big shifts in our world: The perceived value of content (especially “SEO content”) dropped dramatically in many people’s minds because of AI’s writing capabilities SEO became less predictable as a source of traffic and revenue It’s harder than ever for startups and smaller companies to rank for valuable keywords (let alone generate any meaningful traffic or revenue from them) The effect? The middle of the content market has hollowed out. People—like us—providing good, human-crafted content aimed on driving SEO growth saw a dramatic decline in demand. We felt it all year. Fewer and fewer leads. The leads we did see usually scoffed at our prices. They were indexing us against the cost of content mills and mass-produced AI articles. It was a time of soul-searching and looking for a way forward. I spent the first half of the year convinced that the only way to survive was to run toward the fire. We have to build our own AI workflows. We have to cut our rates internally. We have to get faster and cheaper to stay competitive with the agencies offering the same number of deliverables for a fraction of our rates. It’s the only way forward. But then I asked myself a question… Is this the game I actually want to play? As an entrepreneur, do I want to run a business where I’m competing mostly on price and efficiency rather than quality and value? Do I want to hop into a race toward cheaper and cheaper content? Do I want to help people chase a dwindling amount of organic traffic that’s shrinking in value? No. That’s not the game I want to play. That’s not a business I want to run. I don’t want to be in the content mill business. So I decided to turn the wheel—again. Repositioning Part II: Electric Boogaloo What do you do when the whole world shifts around you and the things that used to work aren’t working anymore? You pivot. You re-position the business and move in another direction. So that’s what we decided to do. Again. There was only one problem: I honestly wasn’t sure what opportunities existed in the content marketing industry outside of what we were already doing. We lived in a little echo chamber of startups and SEO. It felt like the whole market was on fire and I had fight through the smoke to find an escape hatch. So I started making calls. Good ol’ fashioned market research. I reached out to a few dozen marketing and content leaders at a bunch of different companies. I got on the phone and just asked lots of questions about their content programs, their goals, and their pain points. I wanted to understand what was happening in the market and how we could be valuable. And, luckily, this process really paid off. I learned a lot about the fragmentation happening across content and how views were shifting. I noticed key trends and how our old target market really wasn’t buying what we were selling. Startups and small companies are no longer willing to invest in an agency like ours. If they were doing content and SEO at all, they were focused entirely on using AI to scale output and minimize costs. VC money is still scarce and venture-backed companies are more focused on profitability than pure growth and raising another round. Larger companies (\~500+ employees) are doing more content than ever and drowning in content production. They want to focus on strategy but can barely tread water keeping up with content requests from sales, demand gen, the CEO, and everyone else. Many of the companies still investing in content are looking at channels and formats outside of SEO. Things like thought leadership, data reports, interview-driven content, and more. They see it as a way to stand out from the crowd of “bland SEO content.” Content needs are constantly in flux. They range from data reports and blog posts to product one-pagers. The idea of a fixed-scope retainer is a total mismatch for the needs of most companies. All of this led to the logical conclusion: We were talking to the wrong people about the wrong things\.\ Many companies came to one of two logical conclusions: SEO is a risky bet, so it’s gotta be a moonshot—super-low cost with a possibility for a big upside (i.e., use AI to crank out lots of content. If it works, great. If it doesn’t, then at least we aren’t out much money.) SEO is a risky bet, so we should diversify into other strategies and channels to drive growth (i.e., shift our budget from SEO and keyword-focused content to video, podcasts, thought leadership, social, etc) Unless we were going to lean into AI and dramatically cut our costs and rates, our old buyers weren’t interested. And the segment of the market that needs our help most are looking primarily for production support across a big range of content types. They’re not looking for a team to run a full-blown program focused entirely on SEO. So we had to go back to the drawing board. I’ve written before about our basic approach to repositioning the business. But, ultimately it comes down to identifying our unique strengths as a team and then connecting them to needs in the market. After reviewing the insights from my discussions and taking another hard look at our business and our strengths, I decided on a new direction: Move upmarket: Serve mid-size to enterprise businesses with \~500-5,000 employees instead of startups Focus on content that supports a broader range of business goals instead of solely on SEO and organic growth (e.g., sales, demand gen, brand, etc) Shift back to our broader playbook of content deliverables, including thought leadership, data studies, and more Focus on content execution and production to support an internally-directed content strategy across multiple functions In a way, it’s sort of a reverse-niche move. Rather than zooming in specifically on driving organic growth for startups, we want to be more of an end-to-end content production partner that solves issues of execution and operations for all kinds of content teams. It’s early days, but the response here has been promising. We’ve seen an uptick in leads through Q4. And more companies in our pipeline fit the new ICP. They’re bigger, often have more budget. (But they move more slowly). We should know by the end of the quarter if this maneuver is truly paying off. Hopefully, this will work out. Hopefully our research and strategy are right and we’ll find a soft landing serving a different type of client. If it doesn’t? Then it will be time to make some harder decisions. As I already mentioned, I’m not interested in the race to the bottom of AI content. And if that’s the only game left in town, then it might be time to think hard about a much bigger change. — To be done: Build new content playbooks for expanded deliverables Build new showcase page for expanded deliverables Retooling the Operation It’s easy to say we’re doing something new. It’s a lot harder to actually do it—and do it well. Beyond just changing our positioning, we have to do open-heart surgery on the entire content operation behind the scenes. We need to create new systems that work for a broader range of content types, formats, and goals. Here’s the first rub: All of our workflows are tooled specifically for SEO-focused content. Every template, worksheet, and process that we’ve built and scaled in the last 5 years assumes that the primary goal of every piece of content is SEO. Even something as simple as requiring a target keyword is a blocker in a world where we’re not entirely focused on SEO. This is relatively easy to fix, but it requires several key changes: Update content calendars to make keywords optional Update workflows to determine whether we need an optimization report for each deliverable Next, we need to break down the deliverables into parts rather than a single line item. In our old system, we would plan content as a single row in a Content Calendar spreadsheet. It was a really wide sheet with lots of fields where we’d define the dimensions of each individual article. This was very efficient and simple to follow. But every article had the same overall scope when it came to the workflow. In Asana (our project management tool), all of the steps in the creation were strung together in a single task. We would create a few basic templates for each client, and then each piece would flow through the same steps: Briefing Writing Editing Design etc. If we had anything that didn’t fit into the “standard” workflow, we’d just tag it in the calendar with an unofficial notation \[USING BRACKETS\]. It worked. But it wasn’t ideal. Now we need the steps to be more modular. Imagine, for example, a client asks us to create a mix of deliverables: 1 article with writing + design 1 content brief 1 long-form ebook with an interview + writing + design Each of these would require its own steps and its own workflow. We need to break down the work to accommodate for a wider variety of workflows and variables. This means we need to update the fields and structure of our calendar to accommodate for the new dimensions—while also keeping the planning process simple and manageable. This leads to the next challenge: The number of “products” that we’re offering could be almost infinite. Just looking at the example scope above, you can mix and match all of these different building blocks to create a huge variety of different types of work, each requiring its own workflow. This is part of the reason we pivoted away from this model to focus on a productized, SEO-focused content service back in 2020. Take something as simple as a case study. On the surface, it seems like one deliverable that can be easily scoped and priced, right? Well, unpack what goes into a case study: Is there already source material from the customer or do we need to conduct an interview? How long is it? Is it a short overview case study or a long-form narrative? Does it need images and graphics? How many? Each of these variables opens up 2-3 possibilities. And when you combine them, we end up with something like 10 possible permutations for this single type of deliverable. It gets a bit messy. But not only do we have to figure out how to scope and price all for all of these variables, we also have to figure out how to account for these variables in the execution. We have to specify—for every deliverable—what type it is, how long, which steps are involved and not involved, the timeline for delivery, and all of the other factors. We’re approaching infinite complexity, here. We have to figure out a system that allows for a high level of flexibility to serve the diverse needs of our clients but is also productized enough that we can build workflows, process, and templates to deliver the work. I’ve spent the last few months designing that system. Failed Attempt #1: Ultra-Productization In my first pass, I tried to make it as straight forward as possible. Just sit down, make a list of all of the possible deliverables we could provide and then assign them specific scopes and services. Want a case study? Okay that’ll include an interview, up to 2,000 words of content, and 5 custom graphics. It costs $X. But this solution quickly fell apart when we started testing it against real-world scenarios. What if the client provided the brief instead of us creating one? What if they didn’t want graphics? What if this particular case study really needs to be 3,000 words but all of the others should be 2,000? In order for this system to work, we’d need to individual scope and price all of these permutations of each productized service. Then we’d need to somehow keep track of all of these and make sure that we accurately scope, price, and deliver them across dozens of clients. It’s sort of like a restaurant handling food allergies by creating separate versions of every single dish to account for every individual type of allergy. Most restaurants have figured out that it makes way more sense to have a “standard” and an “allergy-free” version. Then you only need 2 options to cover 100% of the cases. Onto the next option. Failed Attempt #2: Deliverable-Agnostic Services Next, I sat down with my head of Ops, Katy, to try to map it out. We took a big step back and said: Why does the deliverable itself even matter? At the end of the day, what we’re selling is just a few types of work (research, writing, editing, design, etc) that can be packaged up in an infinite number of ways. Rather than try to define deliverables, shouldn’t we leave it open ended for maximum flexibility? From there, we decided to break down everything into ultra-modular building blocks. We started working on this super complex system of modular deliverables where we would have services like writing, design, editing, etc—plus a sliding scale for different scopes like the length of writing or the number of images. In theory, it would allow us to mix and match any combination of services to create custom deliverables for the client. In fact, we wanted the work to be deliverable-agnostic. That way we could mold it to fit any client’s needs and deliver any type of content, regardless of the format or goal. Want a 5,000-word case study with 15 custom graphics? That’ll be $X. Want a 2,000-word blog post with an interview and no visuals? $Y. Just want us to create 10 briefs, you handle the writing, and we do design? It’s $Z. Again, this feels like a reasonable solution. But it quickly spiraled out of amuck. (That’s an Office reference.) For this to work, we need to have incredibly precise scoping process for every single deliverable. Before we can begin work (or even quote a price), we need to know pretty much the exact word count of the final article, for example. In the real world? This almost never happens. The content is as long as the content needs to be. Clients rarely know if the blog post should be 2,000 words or 3,000 words. They just want good content. We have a general ballpark, but we can rarely dial it in within just 1,000 words until we’ve done enough research to create the brief. Plus, from a packaging and pricing perspective, it introduces all kind of weird scenarios where clients will owe exactly $10,321 for this ultra-specific combination of services. We were building an open system that could accommodate any and all types of potential deliverables. On the face that seems great because it makes us incredibly flexible. In reality, the ambiguity actually works against us. It makes it harder for us to communicate to clients clearly about what they’ll get, how much it will cost, and how long it will take. That, of course, also means that it hurts our client relationships. (This actually kind of goes back to my personal learnings, which I’ll mention in a bit. I tend to be a “let’s leave things vague so we don’t have to limit our options” kind of person. But I’m working on fixing this to be more precise, specific, and clear in everything that we do.) Dialing It In: Building a Closed System We were trying to build an open system. We need to build a closed system. We need to force clarity and get specific about what we do, what we don’t do, and how much it all costs. Then we need a system to expand on that closed system—add new types of deliverables, new content playbooks, and new workflows if and when the need arises. With that in mind, we can start by mapping out the key dimensions of any type of deliverable that we would ever want to deliver. These are the universal dimensions that determine the scope, workflow, and price of any deliverable—regardless of the specific type output. Dimensions are: Brief scope Writing + editing scope Design scope Interview scope Revision (rounds) Scope, essentially, just tells us how many words, graphics, interviews, etc are required for the content we’re creating. In our first crack at the system, we got super granular with these scopes. But to help force a more manageable system, we realized that we didn’t need tiny increments for most of this work. Instead, we just need boundaries—you pay $X for up to Y words. We still need some variability around the scope of these articles. Obviously, most clients won’t be willing to pay the same price for a 1,000-word article as a 10,000-word article. But we can be smarter about the realistic break points. We boiled it down to the most common ranges: (Up to) 250 words 1,000 words 3,000 words 6,000 words 10,000 words This gives us a much more manageable number of variables. But we still haven’t exactly closed the system. We need one final dimension: Deliverable type. This tells us what we’re actually building with these building blocks. This is how we’ll put a cap on the potentially infinite number of combinations we could offer. The deliverable type will define what the final product should look like (e.g., blog post, case study, ebook, etc). And it will also give us a way to put standards and expectations around different types of deliverables that we want to offer. Then we can expand on this list of deliverables to offer new services. In the mean time, only the deliverables that we have already defined are, “on the menu,” so to speak. If a client comes to us and asks for something like a podcast summary article (which we don’t currently offer), we’ll have to either say we can’t provide that work or create a new deliverable type and define the dimensions of that specific piece. But here’s the kicker: No matter the deliverable type, it has to still fit within the scopes we’ve already defined. And the pricing will be the same. This means that if you’re looking for our team to write up to 1,000 words of content, it costs the same amount—whether it’s a blog post, an ebook, a LinkedIn post, or anything else. Rather than trying to retool our entire system to offer this new podcast summary article deliverable, we’ll just create the new deliverable type, add it to the list of options, and it’s ready to sell with the pre-defined dimensions we’ve already identified. To do: Update onboarding workflow Update contracts and scope documents Dial in new briefing process Know Thyself For the last year, I’ve been going through personal therapy. (Huge shout out to my wife, Laura, for her support and encouragement throughout the process.) It’s taught me a lot about myself and my tendencies. It’s helped me find some of my weaknesses and think about how I can improve as a person, as a partner, and as an entrepreneur. And it’s forced me to face a lot of hard truths. For example, consider some of the critical decisions I’ve made for my business: Unconventional freelance “collective” model No formal management structure Open-ended retainers with near-infinite flexibility General contracts without defined scope “Take it or leave it” approach to sales and marketing Over the years, I’ve talked about almost everything on this list as a huge advantage. I saw these things as a reflection of how I wanted to do things differently and better than other companies. But now, I see them more as a reflection of my fears and insecurities. Why did I design my business like this? Why do I want so much “flexibility” and why do I want things left open-ended rather than clearly defined? One reason that could clearly explain it: I’m avoidant. If you’re not steeped in the world of therapy, this basically means that my fight or flight response gets turned all the way to “flight.” If I’m unhappy or uncomfortable, my gut reaction is usually to withdraw from the situation. I see commitment and specificity as a prelude to future conflict. And I avoid conflict whenever possible. So I built my business to minimize it. If I don’t have a specific schedule of work that I’m accountable for delivering, then we can fudge the numbers a bit and hope they even out in the end. If I don’t set a specific standard for the length of an article, then I don’t have to let the client know when their request exceeds that limit. Conflict….avoided? Now, that’s not to say that everything I’ve built was wrong or bad. There is a lot of value in having flexibility in your business. For example, I would say that our flexible retainers are, overall, an advantage. Clients have changing needs. Having flexibility to quickly adapt to those needs can be a huge value add. And not everything can be clearly defined upfront (at least not without a massive amount of time and work just to decide how long to write an article). Overly-rigid structures and processes can be just as problematic as loosey-goosey ones. But, on the whole, I realized that my avoidant tendencies and laissez faire approach to management have left a vacuum in many areas. The places where I avoided specificity were often the places where there was the most confusion, uncertainty, and frustration from the team and from clients. People simply didn’t know what to expect or what was expected of them. Ironically, this often creates the conflict I’m trying to avoid. For example, if I don’t give feedback to people on my team, then they feel uneasy about their work. Or they make assumptions about expectations that don’t match what I’m actually expecting. Then the client might get upset, I might get upset, and our team members may be upset. Conflict definitely not avoided. This happens on the client side, too. If we don’t define a specific timeline when something will be delivered, the client might expect it sooner than we can deliver—creating frustration when we don’t meet their expectation. This conflict actually would have been avoided if we set clearer expectations upfront. But we didn’t do that. I didn’t do that. So it’s time to step up and close the gaps. Stepping Up and Closing the Gaps If I’m going to address these gaps and create more clarity and stability, I have to step up. Both personally and professionally. I have to actually face the fear and uncertainty that drives me to be avoidant. And then apply that to my business in meaningful ways that aren’t cop-out ways of kinda-sorta providing structure without really doing it. I’ve gotta be all in. This means: Fill the gaps where I rely on other people to do things that aren’t really their job but I haven’t put someone in place to do it Set and maintain expectations about our internal work processes, policies, and standards Define clear boundaries on things like roles, timelines, budgets, and scopes Now, this isn’t going to happen overnight. And just because I say that I need to step up to close these gaps doesn’t mean that I need to be the one who’s responsible for them (at least not forever). It just means that, as the business leader, I need to make sure the gaps get filled—by me or by someone else who has been specifically charged with owning that part of the operation. So, this is probably my #1 focus over the coming quarter. And it starts by identifying the gaps that exist. Then, step into those gaps myself, pay someone else to fill that role, or figure out how to eliminate the gap another way. This means going all the way back to the most basic decisions in our business. One of the foundational things about Optimist is being a “different kind” of agency. I always wanted to build something that solved for the bureaucracy, hierarchy, and siloed structure of agencies. If a client has feedback, they should be able to talk directly to the person doing the work rather than going through 3 layers of account management and creative directors. So I tried to be clever. I tried to design all kinds of systems and processes that eliminated these middle rungs. (In retrospect, what I was actually doing was designing a system that played into my avoidant tendencies and made it easy to abdicate responsibility for lots of things.) Since we didn’t want to create hierarchy, we never implemented things like Junior and Senior roles. We never hired someone to manage or direct the individual creatives. We didn’t have Directors or VPs. (Hell, we barely had a project manager for the first several years of existence.) This aversion to hierarchy aligned with our values around elevating ownership and collective contribution. I still believe in the value a flat structure. But a flat structure doesn’t eliminate the complexity of a growing business. No one to review writers and give them 1:1 feedback? I guess I’ll just have to do that….when I have some spare time. No Content Director? Okay, well someone needs to manage our content playbooks and roll out new ones. Just add it to my task list. Our flat structure didn’t eliminate the need for these roles. It just eliminated the people to do them. All of those unfilled roles ultimately fell back on me or our ops person, Katy. Of course, this isn’t the first time we’ve recognized this. We’ve known there were growing holes in our business as it’s gotten bigger and more complex. Over the years, we’ve experimented with different ways to solve for it. The Old Solution: Distributed Ops One system we designed was a “distributed ops” framework. Basically, we had one person who was the head of ops (at the time, we considered anything that was non-client-facing to be “ops”). They’d plan and organize all of the various things that needed to happen around Optimist. Then they’d assign out the work to whoever was able to help. We had a whole system for tying this into the our profit share and even gave people “Partner” status based on their contributions to ops. It worked—kinda. One big downfall is that all of the tasks and projects were ad hoc. People would pick up jobs, but they didn’t have much context or expertise to apply. So the output often varied. Since we were trying to maintain a flat structure, there was minimal oversight or management of the work. In other words, we didn’t always get the best results. But, more importantly, we still didn’t close all of the gaps entirely. Because everything was an ad-hoc list of tasks and projects, we never really had the “big picture” view of everything that needed to be done across the business. This also meant we rarely had clarity on what was important, what was trivial, and what was critical. We need a better system. Stop Reinventing the Wheel (And Create a Damn Org Chart) It’s time to get serious about filling the gaps in our business. It can’t be a half-fix or an ad hoc set of projects and tasks. We need clarity on the roles that need to be filled and then fill them. The first step here is to create an org chart. A real one. Map out all of the jobs that need to be done for Optimist to be successful besides just writers and designers. Roles like: Content director Design director SEO manager Reporting Finance Account management Business development Sales Marketing Project management It feels a bit laughable listing all of these roles. Because most are either empty or have my name attached to them. And that’s the problem. I can’t do everything. And all of the empty roles are gaps in our structure—places where people aren’t getting the direction, feedback, or guidance they need to do their best work. Or where things just aren’t being done consistently. Content director, for example, should be responsible for steering the output of our content strategists, writers, and editors. They’re not micromanaging every deliverable. But they give feedback, set overall policy, and help our team identify opportunities to get better. Right now we don’t have anyone in that role. Which means it’s my job—when I have time. Looking at the org chart (a real org chart that I actually built to help with this), it’s plain as day how many roles look like this. Even if we aren’t going to implement a traditional agency structure and a strict hierarchy, we still need to address these gaps. And the only way for that to happen is face the reality and then create a plan to close the gaps. Now that we have a list of theoretical roles, we need to clearly define the responsibilities and boundaries of those roles to make sure they cover everything that actually needs to happen. Then we can begin the process of delegating, assigning, hiring, and otherwise addressing each one. So that’s what I need to do. To be done: Create job descriptions for all of the roles we need to fill Hire Biz Dev role Hire Account Lead role(s) Hire Head of Content Playing Offense As we move into Q1 of 2025 and I reflect on the tumultuous few years we’ve had, one thought keeps running through my head. We need to play offense. Most of the last 1-2 years was reacting to changes that were happening around us. Trying to make sense and chart a new path forward. Reeling. But what I really want—as a person and as an entrepreneur—is to be proactive. I want to think and plan ahead. Figure out where we want to go before we’re forced to change course by something that’s out of our control. So my overarching focus for Q1 is playing offense. Thinking longer term. Getting ahead of the daily deluge and creating space to be more proactive, innovative, and forward thinking. To do: Pilot new content formats Audit and update our own content strategy Improve feedback workflows Build out long-term roadmap for 1-2 years for Optimist Final Note on Follow-Through and Cadence In my reflection this year, one of the things I’ve realized is how helpful these posts are for me. I process by writing. So I actually end up making a lot of decisions and seeing things more clearly each time I sit down to reflect and write my yearly recap. It also gives me a space to hold myself accountable for the things I said I would do. So, I’m doing two things a bit differently from here on out. First: I’m identifying clear action items that I’m holding myself accountable for getting done in the next 3 months (listed in the above sections). In each future update, I’ll do an accounting of what I got done and what wasn’t finished (and why). Second: I’m going to start writing shorter quarterly updates. This will gives me more chances each year to reflect, process, and make decisions. Plus it gives me a shorter feedback loop for the action items that I identified above. (See—playing offense.) — Okay friends, enemies, and frenemies. This is my first update for 2025. Glad to share with y’all. And thanks to everyone who’s read, commented, reached out, and shared their own experiences over the years. We are all the accumulation of our connections and our experiences. As always, I will pop in to respond to comments and answer questions. Feel free to share your thoughts, questions, and general disdain down below. Cheers, Tyler

Building Business Development/Sales Pipeline
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Building Business Development/Sales Pipeline

Hey all! Happy weekend wherever you may be! Wanting to get some advice and insight into a couple areas as mentioned in the title. Background is the following: My Partner and I started our company about in 2021. When we kicked off we were building a control and camera vision system for automating and optimizing indoor vertical farms. We got to early mvp but market was not as big and barrier to entry was high. So we pivoted early 2023 to utilize components of our technology in a wildfire detection and risk analysis platform. Happy to say we are once again at MVP but need to get PMF and pipeline going both with revenue generating clients and pilots/demos. Through this period we’ve kept the lights on by running a consulting service and digital agency. We’ve also pushed out a couple of AI tools to market. Effectively I need to build out a strong pipeline for each vertical and associated sales team. Right now spread too thin trying to conduct sales and business dev on each front. Challenges: Wildfire: Business to Gov relationships so need to build for that. Additionally early stage technology so imo relationships are critical. Additionally need to take advantage of grant funding. Target Markets: Canada, USA, Mediterranean, Northern Europe/Scandavian Countries. Consulting and Agency: Things feel dry… we have a recurring client list but we want to grow this channel exponentially, focusing on RFP’s and med to large company profiles rather then the current SMB. Our current activités are mediocre imo for outreach and connection. AI Tools: I believe these are great opportunities. TLDR 1)sales based assistant as well as 2)central AI aggregation with prompt repository. Business Dev Energy into this is basically focused on digital means. In the process of generating video content to push via ads and online social platforms. Challenge: low engagement right now users signing up but no commitments to purchase. Need to evaluate value offer and feedback on PMF. From the sales team side, effectively need to generate the sales so I can expand the team and grow accordingly. I’m a huge proponent of commission based compensation. Also open to a base salary. However anyone I onboard at this moment would have to be commission cause cash-flow. On that front, what are current commissions structures looking like for people? What’s engaging what’s worth taking a risk what is just a huge no? On the challenges for the product lines any feedback questions and even poking holes is appreciated! Thanks!