Personal Essay: From High-Growth Tech Startup to Exit: My Journey of Failure

September 1, 2023 thehrobserver-hrobserver-highgrowth

So what do you do?” His gaze skims me, sizing up my appearance, my essence, weighing the potential utility to be exploited. I’m at a ReFi DAO networking event in Lisbon, surrounded by those on a mission to rescue the world, or maybe they’re pursuing ventures so cryptic that sounding impressive suffices. It’s not quite the tech domain I once navigated, more like a fusion of that and the social entrepreneurship arena. Nonetheless, I’m at home here — I know the terrain, the strings to pull, how to shine. Except, my response to the classic question isn’t what it used to be three years back.

I’m fully invested in motherhood right now. I’ve…” I hear the disappointment even before my words fully escape, feel his dismissal. “I apologize,” he interjects, “an old friend just walked in. Catch up with you later, perhaps!” And he’s gone. A few years ago, that answer might’ve dented my pride, but today, such reactions are the norm. “How could someone like you fail?” “What went wrong? You were an A player!”. The remarks roll in, even the in-laws contributing their fair share of disapproval. In the end I’ve started wondering myself — what did actually go wrong? How did I fail my startup?

Founder Relations

Co-founding is pretty much like being in a marriage setup, as many have pointed out before. And just like in a marriage, having the wrong partner can turn things toxic and disempowering. My co-founder challenge came from being close friends — we let our friendship cloud our decision-making. Issues that arose often got tangled in emotional messiness instead of being addressed like operational or leadership hurdles. I turned a blind eye to many things, overstaying in this friend-foundership way longer than I should’ve, even when others warned me about the red flags.

My friend, my co-founder, was (and probably still is) a tech genius, a mind with a beautiful complexity that taught me much over the years. But he also had facets I chose to ignore. Many promises were unkept, and it all came crashing down eventually. Stripping emotions, I crunched numbers and realized that I’d been shortchanged by a year’s salary, funds diverted to company investments I wasn’t aware of, strategic moves made without my input that I couldn’t support, books and paperwork that never materialized. In the end I confronted him, but ownership and financial access remained off-limits, sealing our personal and professional split. We reached our dealbreaker scenario.

In hindsight, the missteps are clear. But everything seems easy and clear when in hindsight. Yet, I have no regrets about operating in good faith with sincere intentions. Because living in fear, mistrust, and constant scrutiny just isn’t my style — I don’t believe that such an environment breeds greatness.

Those times moved swiftly, decisions aplenty, and I misplaced my trust. That’s the bottom line.

Here’s what I wish we’d talked about before embarking upon this journey together:

  1. Alignment of Values and Ethics: Ensure that your personal values and ethical standards align, as these factors significantly influence decision-making and shape the startup’s culture. We aligned theoretically, but not practically when it came down to things such as how we treated those that we hired, what type of culture we wanted to have.. and many other areas.
  2. Vision of Success: Discuss your co-founder’s vision of success — is it a rapid financial exit, building a large company, or cultivating a small, tight-knit team without a predefined exit strategy? All of these can be great — if you’re aligned.
  3. Perceptions of Failure: Define what failure means to each of you and how you would handle setbacks and challenges. Managing difficulties is an inevitable part of the journey.
  4. Work-Life Balance Expectations: Address expectations around work-life balance to avoid burnout and ensure a healthy partnership. We didn’t and I can quite frankly reveal that our way of working was brutal on general health and wellbeing. I managed to suffer from several burnouts and even ended up at a buddhist retreat.
  5. Consult Previous Partners and Colleagues: Engage with previous partners and colleagues to gain insight and gather feedback before entering a partnership.
  6. Stress Management Approach: Understand how your potential co-founder handles stress to gauge compatibility in high-pressure situations.
  7. Dealbreaker Scenarios: Identify and communicate dealbreaker scenarios — situations that would lead to reconsidering or ending the partnership.
  8. Shared understanding of Quality Standards: In my experience, individuals can greatly differ in their approach. For me, I can’t tolerate subpar quality. Even a typo or a minor UI flaw triggers my inner perfectionist. Mediocre work pisses me off. However, not everyone shares this viewpoint. Seek a partner who resonates with your dedication to quality and can hold you accountable when needed. What I really admired about my co-founder was our shared commitment to maintaining high standards. If either of us slipped, we gently (or forwardly) nudged each other back on track.
  9. Equity Distribution: Clearly determine the initial ownership split between co-founders. The distribution should reflect contributions and involvement levels accurately. Don’t think that this is easy, and, if you are a woman without a tech background you might find yourself underestimated or undervalued compared to other team members (Surprise — I was!). But here’s the truth: that mindset is flawed! Don’t sell yourself short. Despite the abundance of business suits and code junkies in this world, what truly counts is your unique combination of skills, network, and individuality. Sure, we’re all replaceable to some extent, but your story? That’s one-of-a-kind. Don’t buy into the myth that you’re just another cog. You’re a diamond in the rough sea of sameness. Your distinct story and perspective are irreplaceable. If your partners do not share that perspective tell them to find another business suit. There’s so many of them out there anyways, right.
  10. Legal Agreements: Consult with a lawyer to draft legal agreements, such as a founders’ agreement or a shareholder agreement. These documents outline the terms of the partnership, responsibilities, equity distribution, and more. This is pretty basic, but pretty essential.

Eliot Peper has written a really great book about this topic generally — can highly recmmend reading Uncommon Stock.

Roxanne has published a longer form of this piece here.

Roxane Maar


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