I didn't know it was a dumpster fire. All I knew is that I wanted to be CEO…the one thing I had been chasing since I first entered corporate life. I wanted to be "the guy." And I was ready. Or at least, I thought I was ready. I was in the midst of a stellar revenue growth run as VP of Marketing at TeePublic, helping grow the ecommerce marketplace from single digit millions to well over $100m over the course of 6 years. I had a team operating on all cylinders. Our founder and CEO had retired earlier in the year and I felt it was time to move on as well.
And then I got a call…
But in a very real sense, I was not ready in the slightest. Nor did I really want to be CEO.
It was from TeeFury, a small-time competitor of TeePublic that had it's heyday back around 2015 but was still puttering around as a daily deals website. And they were on the lookout for a new CEO that could rescue the brand and turn it profitable. The search committee was impressed with my track record and loved the fact that I had success with two of TeeFury’s competitors. So, they offered me the chance to run the company.
Instead of thinking about it and asking questions like:
Are we profitable today, or do you expect me to make us profitable?
How many months of cash do we have in the bank if growth flatlines?
Are you hiring me as a CEO to grow…or as an EMT to resuscitate?
I asked questions like "when can I start?"
The problem was TeeFury was failing. It experienced 5 straight years of declining revenue. It was hemorrhaging creators and it's content moat had eroded. My being hired was a last ditch attempt to save a company whose fundamentals were in shambles.
Come for the bragging rights of being CEO. Stay for the dumpster fire.
But I didn't care. I was CEO. I did it! I made it! I climbed the corporate ladder. I won! In the wise words of Dr. Ian Malcolm from the documentary Jurassic Park, "Adam was so preoccupied with whether or not he could, he didn't stop to think if he should." The CEO title was precious to me. And while it didn't turn me into Gollum, it didn't do me any favors.
What happened? Did I fix TeeFury? Did I put out the dumpster fire?
The short answer is "not really." Don't get me wrong, I was able to move the company in the right direction. We hit profitability after 3 months (but not consistently) and our revenue stopped declining year over year. But it wasn't enough. It was too little, too late. I didn't succeed fast enough for our cash runway. I lasted a year before I was let go.
Looking back, my mistake was with my approach (and that I thought I was hot shit who had a savior complex). I thought I could apply the same tactics and tricks that worked at TeePublic and see the same type of success at TeeFury. Only the problem was, what got me "here" wasn't going to get me "there." I failed to understand my playbook was outdated. It worked…for TeePublic. When we were in growth mode. When we had money to invest in top of funnel activities. When we were one of the dominate players in the market. The playbook worked for a completely different internal and external context. And, ironically, TeeFury failed because of my TeePublic playbook.
I wrote the playbook for a company in growth mode. TeeFury was in triage mode. I tried to scale a fire instead of putting it out. And that's what happens when you're dealing with a dumpster fire: you reach for the tools that made you successful before. But those tools don't work in every situation. The playbook that builds growth is not the one that saves a company from collapse.
If I could do it again, I wouldn't have reached for the TeePublic playbook. That playbook worked because TeePublic was operating in a different context: massive creator supply, a loyal community, strong margins, and a market tailwind that rewarded scale. TeeFury was different. The content moat was gone, creators were leaving, and the big boys like TeePublic were muscling TeeFury out of Google auctions.
If you are brought in to save a dying company, you should know that you're probably not going to save it. Sorry. That's not me being harsh or questioning your skills and experience. It's just the reality of the game we play. Most companies are going to fail. Maybe not shut-the-doors fail, but not grow. So set low expectations. Understand the battle you're fighting and your odds of winning.
Second, understand that what got you here won't get you there. What made you successful in the past doesn't transfer over completely to a new situation. Playbooks are not universal. They're situational. A turnaround requires a different muscle than scale. Triage before growth. Stabilize before strategy.
What I wished I did was to get to first-principles thinking. Instead of slapping on the TeePublic playbook, I should have broken the business down to its atomic structure, diagnosed the real constraint, designed a focused intervention, and only then deployed action. I should have gone in eyes wide open.
What is the real problem, stripped to the core truths?
The moat was gone (our creators were leaving the platform en masse).
Revenue was in free-fall for 5 years and couldn't support OPEX.
Larger competitors were muscling us out of Google auctions.
The daily-deals model wasn't unique or sticky with users anymore.
What is the real constraint?
Supply attrition. Creators left for other platforms giving them more money, more reach, and smarter tools that freed up their time to create more.
Negative feedback loop: fewer creators → weaker catalog → fewer buyers → more creators leaving.
While the major players were consolidating content and generating unique content quickly, we were playing the hits.
Can we rebuild a supply edge fast enough?
Hypothesis: If we secure even a small group of exclusive creators, revenue stabilizes because users have a reason to return daily.
MVP test: lock in 10 high-value artists with guaranteed payouts + prominent placement.
KPI: Repeat purchase rate in 30 days.
Run it, log it, decide fast.
If it works → scale to 50 artists.
If it fails → pivot the model (subscriptions, community drops, licensing) or admit the fire can't be put out.
That's what I should have done. I would have asked the uncomfortable questions about cash, churn, and unit economics. I would have aligned with the board on whether they wanted a builder or an undertaker. And I would have admitted that the ego boost of being "the guy" wasn't worth the cost.
What I did was the wrong answer to the right question. What I should have done was start with the question itself: what does this business need to survive the week?