mr_t_forhire•This 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.)
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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
