Hi WSO!
I left a Director, GTM role in 2020 to build a business in B2B Healthcare Technology. I closed the business 2.5 years later. This post will detail five (5) lessons that I learned the hard way:
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.
Based on the most helpful WSO content, here are five hard lessons from your startup journey, along with insights that align with broader entrepreneurial experiences:
Resetting Professional and Social Status
Entrepreneurship often strips away the external validation tied to corporate roles. As you noted, responses to emails and calls can dwindle, and the lack of a pre-existing network or financial backing can make the journey even tougher. Leaning on close relationships and intrinsic motivation is critical during this phase.
Self-Directed Work and Strategic Vision
Transitioning from a structured corporate environment to managing all aspects of a business is a steep learning curve. As you experienced, setting a strategic vision, breaking it into actionable tasks, and delegating effectively are essential skills. The constant need to switch between strategy and execution is a hallmark of startup life.
Facing Failure for the First Time
Many founders, like yourself, encounter failure on an unprecedented scale. The emotional toll of owning every aspect of the business—strategy, sales, fundraising—can be brutal. However, as highlighted in WSO threads, failure is often the best teacher, building resilience and emotional fortitude.
The Importance of Business, Legal, and Technical Alignment
Your realization that a product isn't truly "in-market" until business, legal, and technical hurdles are cleared is a crucial takeaway. Many startups falter because they underestimate the importance of regulatory compliance, legal protections, or refining their product to focus on core value propositions.
The Reality That Nobody Is Coming to Save You
The stark truth of entrepreneurship is that success often hinges on your ability to persevere without external rescue. As WSO discussions emphasize, the journey is long, uncertain, and requires immense personal sacrifice. Yet, even in failure, the skills and lessons learned are invaluable.
Aftermath and Reflection
Your post-venture success—landing a high-paying role and regaining personal health—underscores a key insight from WSO: the entrepreneurial experience, regardless of outcome, is highly respected and applicable in other professional contexts. The resilience, adaptability, and strategic thinking you developed as a founder are assets that shine in any role.
Your story is a testament to the grit required in entrepreneurship and the value of the lessons learned, even when the outcome isn't as planned. Whether you return to owning a P&L through W2 or another venture, you're better equipped for the challenges ahead.
Sources: Advice from an ex-IB MD - The Importance Of Failure, From PE >> Startup >> Back to PE, 6 Lessons Learned After Leaving Finance For Entrepreneurship, What Harvard Business School is Teaching This Tech Entrepreneur
Fantastic post, SB’d.
Glad to hear you’re doing better too.
any thoughts on what someone can do to accrue the emotional reps/develop the emotional callousness prior to taking the leap?
That's the thing. There really isn't any amount of preparation you can do. Just take the risk and trust yourself to figure it out.
I keep coming to wso for great posts like these. Invaluable lessons here
As someone who's interested in going the startup route, when would you have thought it was too early? Do you wish you gave it a shot earlier?
Currently in my senior year of undergrad, going into IB after graduation and trying to figure out when is truly too early (realizing that there's not necessarily a clear cut answer)
I'd say it depends on the type of business you want to start. If it's consumer driven party planning platform aimed at college kids, then senior year of undergrad isn't too early. If it's a cloud security platform selling to F500 CIOs, you need to get years of industry experience.
There's minimal downside in getting experience at a high growth start up on your resume, quit and start a company. Learn from people that are building a business and get in early enough that you can wear a lot of hats. That's going to be better than any schooling you could do and allows you to learn from others' mistakes when you start your own company.
Great to hear from someone who isn't afraid to voice their experience that didn't work out. Far more important than the typical success stories social media is inundated with.
Knowing what you know now, if offered a chance to restart your life, would you still go through with this?
Good question. Yes, I would. Leaving the corporate world and bootstrapping a business was an extremely formative experience that I think I did at the right phase of my life. I have absolutely zero (0) impostor syndrome now as a technology business professional. Through application, I forged the mindset of a 'builder' and 'operator'. I learned to live alone, in a reality that I manufacture, to stay obsessed with something all day and for years. I am proud of all of these features of myself and I don't how I would have acquired them otherwise.
Congratulations on your courage to try it, follow through and pick up the pieces and find a new path for you. Maybe the time will come again and this prior experience will be valuable. Your worth is for you to define, as nobody knows your journey as well as you do. Thank you for sharing.
I'm always extremely interested in the post-startup-failure details of these stories, so thank you for sharing where you are today. I have a few questions:
I’ve operated portfolios of senior living communities. I read your story as if the other side was me (dragging feet on the docusign, liability aversion, investors/owners priorities like paying the mortgage, pricey conference marketing channels, fortress inaccessibility). Part of the problem I think is the inherent difficulty to convert sales within my industry. Were you prepared for this?
I empathize with you and mostly blame the sector you were trying to crack. Not to say there isn’t good opportunities to innovate and capitalize on, but there are headwinds that I’ve observed first hand.
Pick a sector that is the opposite (customer needs to move fast, unregulated, investors/owner priorities are massive growth which you can grow alongside, wide range of effective marketing channels, and decision makers are accessible and of various status levels) would be my advice (or at least 50% of those attributes). Problem is you’ll face massive competition and limited barriers to entry (I think strong sales channel in a difficult sector to penetrate is a competitive advantage). That’s the flip side.
I feel for you and glad you landed on your feet. Thanks for sharing.
Great post. 11/10 respect for the attempt. Glad you landed on your feet.
Should’ve listened to Jensen Huang, who literally told aspiring entrepreneurs to not start a company and that he wouldn’t do it again. Many other founders say the same thing. The expected value is just too low.
True entrepreneurs are maniacs driven by God complexes
When I’m asked for advice by aspiring entrepreneurs I always have to start with something like, “just want you to know that I’ve become risk adverse over time and somewhat jaded, and that I don’t want to discourage you from doing something based on my personal views at the moment. You often need ignorance and a lot of positivity to start a company. What I’m going to say, you need to think about and plan for, but don’t dwell on it.”
I think it's more than acceptable to fail at your first business, good for you for trying. I have been in the game since I was 18 or 19 and I'm in my early 30s now. ALL of my friends that stuck with entrepreneurship make a lot more than we could have via W2.
Not saying it's just the right path for everyone but something to consider! It might take 3 - 5 tries before you stumble into an excellent business and make good money...
Some people get lucky with their first business, and for others it takes a few tries. No shame in fucking up a few times before getting lucky!
Hard agree here. I usually tell people that they shouldn't start a company if they're asking for advice. If that's enough to deter them they weren't going to be able to stomach the inevitable failures that come with the journey.
I remember the first 12 months after quitting my job to explore the "idea maze" to start a company and it was failure after failure. The main learning was to fail quickly and pivot until there was some semblance of founder market fit.
Your 2nd and 3rd points are really what it's all about, the 2nd is functional and the 3rd motivational (as it's required to have the necessary motivation to keep moving forward).
No longer have a boss giving you work: 100% and likely the reason why most fail at building their own biz. Highly recommend reading "The E-Myth: Why Most Small Businesses Fail and What You Can Do About It", by Gerber. I've read it at least 10 times and it meant something different to me at each stage of my business.
Strip away the income for a second. Performing tasks for your boss and deciding what tasks need to be done (and when) are two VERY DIFFERENT things. What you'll find in the latter is that learning how to work on meaningful (revenue producing, and critical operations that are required for revenue to book) are all that really matter, at least initially. So forget about 9-5 or 9-9 or X. You work long hours making sure you're getting checks and figuring out how to deliver on your promise (product or service neutral). Do I look at emails? Do I return that call? Do I meet with a vendor? Do I make cold calls? Do I work on the prototype? All of these things and more have to be done but you have to figure out by who and when. When you first start, most likely the anser is always by You. But when and how is important. The skillset you learned in college and your first few yrs on the job are not aligned with this mentality. You were used to performing a task well, ahead of schedule, and profitably. But the what and why to do X was determined by someone else. The E-Myth breaks it down to Entrepreneur, Manager, and Technician. You were basically a Technician. Becoming a Manager and then an Entrepreneur is very difficult as it takes a totally different skillset, especially for those type A, high achievers who simply followed a path.
You've probably never failed: Since you can recall, teachers, coaches, your parents, and your bosses have given you a goal, and you've blown it out of the water! That's great. Congrats! But now, nobody cares about that. You work on the wrong stuff (per point above) and your business fails (You run out of capital, you lose employees, you lose customers, etc.) and you can't figure it out. Why did this happen? The reality is there are no excuses. It's all about you figuring it out.
I was that never fail guy. Then my first business failed miserably. Almost went into personal bankruptcy. Learned a lot along the way, mostly to fight the battles that were worth fighting, resource what was worth resourcing, build processes to scale, etc. Next business was /is a big success. I learned a day of work is not about what you did (time and effort) but far more about what impact you made (results). I'd rather work an hour per day and drive the business / create new opportunities than 10 hrs and work on minutia that likely doesn't matter in the least (like all those model footnotes that no one will ever read).
Being an entrepreneur is a mindset. It uses very different muscles than being a star employee. At the end of the day, you either have it or you don't. But if you want freedom, it's a great way to live. Just be ware that freedom includes freedom to fail!
You also need to just be able to flat out sell (regardless of product, service, market). Business is about revenue and revenue is about selling. They don't buy. You sell. Without those initial checks you never have proof of concept. You need to be able to let your customers underwrite your expansion when you're just starting out.
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