My Startup Failed – Five Hard Lessons

If you are bootstrapping, your professional and social status, superficially, are reset to zero.

When I started to socialize my jump off the deep-end, you can feel those who were waiting for you to fall. That was infuriating. Professionally, emails / InMails / calls that were once promptly answered went stale and require several, demeaning pings to get a reply. I do not come from money and I went to a state school. Had I had a different network to line up a pre-seed / seed before leaving the corporate world, this would have been different. Lean on family, true friends and intrinsic strength while building your business. If you're like me, you're starting from ground zero.

You no longer have a boss giving you work; It is on you to manufacture work across all business functions.

I was used to having work scoped for me and completing it within a given time frame. I had to learn how to set / manage a strategic vision, break that down into work products and delegate out those work products to completion. This was a very difficult adjustment for me as a 28-year-old and probably took me around six (6) months to catch my footing. In the end, the strategy lived in a set of investor Google Slides, breaking down work products existed in my leather padfolio and delegation happened via Slack to contractors sourced from UpWork. You have to gear switch between strategic and execution. I spent every idle second I was awake thinking about the business. The work is never finished.

You've probably never failed in your life. This is different.

I had never failed up until this point in my life. Starting a technology business changed me. I owned the strategy and so when direction was incorrect, that was on me. I owned sales and so when we'd have a customer with a Docusign + terms sitting in their inbox for a demoralizing amount of time, that was on me. I owned fund raising and so when we got denied by YC, Sequoia, 50+ VC firms, Angels, etc..., that was on me. You're failing over and over and over again with your career trajectory at stake, your personal savings on the line and your whole team is watching. You learn, tactically, how to do all of this stuff correctly through the reps but going through this process is brutal. Because of this experience, in business and sometimes in life, I am emotionally callous.

Business, Legal, Technical (BLT): Your product is not 'in-market' until all three (3) are solved.

I figured out the business model 1.5 years in: Sell it like 'valet-trash' to senior living operators to boost their NOI and they pass down costs as value-add amenity. I figured out the technical product 2.0 years in: two of our features are 'morphine', the rest are 'nice to have'. Tear out all the 'nice to have' and Sprint to making the 'morphine'-features enterprise-ready. We were about to go-live on our product in two (2) facilities but hit a legal block: we needed to pony up for a REAL MSA (vs. shit I drafted up) for true legal protection ($20K) and we needed our product certified by UL to be honestly regulatory compliant ($80K). Which leads me to my final point...

Nobody is coming to save you.

I didn't make it to the point where I had leverage over investors for fair terms. I had burned 2.5 years worth of my own savings, 401K, etc... and morale on the team was low because the funds were running dry. When we got to the legal block Winter '23, VC funding for seed evaporated and I had 'unfinished IP' without a balance sheet. I remember sitting in my in-law's basement when reality hit that I had busted out. 2.5 years of the hardest work of my life with no monetary success to speak of. And as true as it was in the beginning, it was in the end - nobody is coming to save you.

Aftermath:

I landed a $300K/YR job 10-days after I busted out. Getting the job made the last 6 - 12 months of running the business feel like Stockholm Syndrome: I'm not worth $100K investment as startup founder but $300K/YR as a W2 IC? I had the income now to push the business over the hump, but that would've required me to restart the engagement with the two (2) facilities, rally the troops and moonlight my duties at business. I was fucking burned out. I could not do it.

I am in a better place today. I live in Manhattan with my wife and baby, living a 'human experience' after having spent a long time in isolation. I fixed health issues (high blood pressure, GI, sleep, etc...) that piled up over the course of the venture. I L+1'd to another FAANG and am slated to clear $500K/YR. I thought my story as a founder would have been all-for-not without an exit that I could put on LinkedIn. That's a farce. Turns out people respect those who really went for it regardless of outcome. The experience is broadly applicable and comes through every day in my work.

Whether through W2 or my own venture, I'll be ready for the opportunity to own P&L again.