Why I failed as CEO
After 11 years of running marketing and design teams for ecommerce print-on-demand marketplaces and seeing lots of success, I took on a role as CEO of a fledgling competitor. I thought I knew everything about how to make this specific type of company grow. I had the playbook. I had the pedigree. I had the experience. I was confident that all I needed to do was replicate what worked for me in the past and I’d be able to save a sinking ship.
I was wrong.
The company was still hemorrhaging money when we decided to part ways. I did not stop the downward spiral quickly enough. I did not deliver success. I did not finish the job.
Why?
The answer is simple: I started with the wrong assumption. I assumed that all ecommerce print-on-demand marketplaces act the same way, from their marketing mix to their information architecture to their supply-side economics. Armed with that assumption, I wrote a 6 page strategic plan for the competitor I was taking over for, borrowing concepts and tactics that worked in my previous roles at other companies. The problem was that these concepts and tactics worked under different and outdated circumstances. The competition had matured, the marketing environment had changed, and most importantly the supply-side of the equation had ceased to be a strategic power. What began as a cornered resource had morphed into a commodity, and the brand’s unique selling position moat had eroded.
And I didn’t see it. Or refused to see it. Or thought it didn’t apply to me.
So I pushed forward with my roadmap, imposing an ill-fitted growth program onto a company that had a different set of problems I was too blind to see. I was delivering features, not learning to solve the customer’s problem. I wasn’t validating my learning, applying a rigorous method for demonstrating progress and discovering valuable truths about the company’s present and future business prospects.
When the results weren’t coming in, I’d pivot to another chunk of my roadmap.
Performance-based pMax campaign buckets on Google Ads not working? Switch to rearchitecting the site for SEO traffic.
Full-funnel Facebook account structure with Advantage+ Shopping not working? Switch to CRO improvements.
Automated email updates not working? Switch to optimizing and leveraging supply-side unit economics.
Pivoting is fine, when it’s based on lean thinking that seeks to eliminate waste and maximize value in any process or system using a unit of measurement called validated learning tied to quantifiable KPIs. But I wasn’t thinking like this. I was scrambling to validate I wasn’t a one-hit wonder. I was scrambling to validate I could run a company.
A better way to approach this situation would be to use the principles found in The Lean Startup by Eric Ries. Principles that were engrained in me by my former boss and mentor. Principles that I threw aside in pursuit of fame, glory, and quick wins. Principles that I thought I didn’t need to repeat since I already went through them at my previous company. Namely…
Validated Learning: running frequent experiments that test each element of a company’s vision
Build-Measure-Learn: building and iterating on MVPs tied to qualitative and quantitative feedback loops
Innovation Accounting: a quantitative approach allowing us to see whether our iterations are working
I bypassed the validated learning principle. I thought I had already “validated” what worked in this vertical. I didn’t create short-cycle feedback loops. I thought the marketing community had already done that work for me and provided me with the most up to date marketing playbooks. And I never took a quantitative approach to the fine tuning iterations.
Although I failed, I also realized I went through a tremendous period of growth both personally and professionally. Here are a few things I’ve learned:
Climbing the corporate ladder isn’t for me. I got to the top. I finally arrived. I was validated. But it wasn’t worth it. It sucked the life out of me. I now understand that I don’t ever want to run a company again. I’m not that person. Rather, I’m a great consigliere. I prefer to focus my time and energy on the marketing side of the business. That’s the one area that invigorates me.
Speed is a superpower that must never be compromised. Minimize the total time through the build-measure-learn feedback loop. While that doesn’t mean we should disregard things like Google’s and Facebook’s campaign learning phase, it does mean that something in the company pipeline should be finishing a feedback loop on a weekly basis.
You can’t go at this alone. Having a mentor or a group of peers you regularly talk to and confide in is crucial to your personal and professional success. Lone rangers do not exist. I would be lost if I didn’t make and strengthen connections in a specific marketing community and in my personal network.
My crash-landing taught me the most valuable lessons of my career. The "playbook" approach to leadership is a recipe for disaster if blind to individual circumstance. Instead, I should have embraced lean startup principles. The sprint for quick wins blinded me to the slow, iterative dance of progress. Something I vow to never fall for again.