Regreting Not Doing a Startup

I did one for about 6 months. It flamed out hard. My co founders and I parted ways. We had no idea what we were doing and it showed. Had we persisted we might have succeeded, but honestly who knows or cares. You have to ask yourself what it is you actually want from starting a business.

Is it to become a wealthy and famous billionaire? Don't bother unless you have all the pieces stacked in your favor.

Is it to do something you're passionate about? Find a way to do that anyway, whether it's through working with friends on it, working for someone on it, or working by yourself on it. You can still do that with a day job, just try to limit all the other things in your life that might distract you.

Is it to be your own boss? You're not gonna ever be your own boss. Your boss is the person who pays you the money. You can only be your own boss by achieving financial independence which you can do with similar amounts of risk in other ways.

Is it because you hate your job or chosen career? Entrepreneurship amplifies, not limits, the effects of that.

Most successful businesses are started by people in their mid careers who have developed a solid network and good set of skills as well as a decent financial cushion and sent their kids of to be independent of them financially.

I very nearly did a startup with a friend. We had a bit of seed money and were accepted into an accelerator, and had a decent beta. But we had major concerns about the market, which seemed to be a bit of a fad, so we pulled out at the last minute. I don't regret that decision at all - within a couple years the primary competitors failed and Amazon ate their lunch.

What I do regret is never finishing my side projects. I recently stumbled across a little website that my boss had paid me $50 to make for his cousin years ago. It was a slick but very simple site that basically just played a few useful audio files. The site now accepts donations and has been wrapped into paid iOS and Android apps that have thousands of downloads. It kills me that someone has made thousands of dollars off of that dead-simple weekend project. Over the last 10 years there has virtually never been a time when I wasn't working on a side project, and yet I haven't actually launched and monetized a single one.

i regret working myself into early alcoholism and it costing me my marriage.

i look back on life now and realize that me being a workaholic wasn't necessary. i was making damn good money with the career i had, but always needed MORE. wish the old me could tell the young me that you're rich enough and if you really want to make an impact on this world, be one of the few in your generation to celebrate a 50 year wedding anniversary.

my friend... if you're married, go home and kiss that spouse of yours.

I'm not the archetype you were asking for, but I am later-ish in my career (40 years old). I co-created a startup not all that long ago (little over a year). I don't regret creating a startup, but it is very very hard at times in ways I did not anticipate. So, there are times when I'm very envious of my former self. Where I got to deal with the perils of regular employment rather than the perils of being an employer. Thoughts like, "Ah, I remember the good old days when this kind of thing was somebody else's problem to deal with. Those were good times. Good times. Welp... (rolls up sleeves to try to figure out the least bad decision from a mountain of uncertainty)"

That's despite having previously operated a moderately successful small business and also helping lots of other companies take on difficult technical challenges and get their products to market. So, there are a lot of things that I had my eyes wide open to that sometimes less experienced founders I know end up a bit blindsided by.

I can't speak for anyone else, but I can say for myself that if my motivation for undertaking this were rooted primarily in the possibility of regretting not having done it, said FOMO would probably not provide the sustaining fortitude necessary to keep pushing and pushing and pushing through the numerous challenges in fundraising, development, go-to-market execution, etc. etc.

So, my only real bit of commentary would be to do a startup because you're dead certain that's the thing you want/need/should do to achieve some goal about something you want to change about the world, the marketplace, and/or the state of technology, etc. I'd not suggest doing it on the fear of regret of not doing it. If that makes any sense? That said, if you have a goal or ambition like that, then I'm always supportive of folks who want to go out there and grab ahold of entrepreneurship and ride it either into the dirt or into the sunset.

I'm the opposite of the person you're asking for, but I'll take a stab. I have the academic pedigree to have worked in a lucrative scientific / banking / management field, but instead chose to take an entrepreneurial path. I could likely have made more money (risk adjusted) on the other path, but am thankful on a DAILY BASIS that I'm a pirate, and didn't join the navy.

Had I not chosen the entrepreneurial path, I'm confident I'd be the person you're asking for: late in my career and regretting not starting a business.

Nope. I refuse to regret my past choices, so that I can be happy with my situation. If you gambled and won, it might have been a bad bet. If you gambled and lost, it still might have been a good bet. No sense in regrets. Best of all possible worlds, and all that.

Before you regret something you didn't do, ask yourself whether you understand that thing well enough to regret it. Why did you want to do a startup?

For example, one popular reason is "I'm my own boss", but that's largely wrong. If you're trying to make money, you have bosses. Going from a salaried job means going from one or a few bosses to many, many bosses. Depending on the startup, these could be a multitude of consumers, a few big clients and/or investors. These bosses will not tell you directly what to do, but will rather stop paying you, or never pay to begin with if you don't do what they want out of you.

You needs and wants about what you want to do is probably very different from what your bosses will pay you to do, and adjusting your needs/wants/ideas to what will pay is what we call "finding product-market fit". Yes, new markets arise, and sometimes someone extraordinary will mold the market to themselves, but largely you'll be molding yourself to the market.

This is not to say being your own boss is BS - you still get plenty of autonomy and are the final decision maker. The layers between you and the market are extremely thin, so the highs are higher and the lows are lower.

I recommend side gigs. I co-founded a reasonably successful business (5 employees) from a side-gig (i was supporting getting remote sensor data remotely from a modem into a form easily red by clients).

Side gigs are reasonably risk free and will grow or shrink organically. You're not trying to force a market. The question is do you know something that works as a side gig? If so go for it.

Remember that the big idea->millions in venture funding->unicorn or bust path isn't the only way to go. That's a very stressful path.

No. You can start a startup at any time.

What people mean when they regret not doing a startup they mean they typically regret not trying to start one when young, having it become a booming success and then reap the rewards for a larger portion of their lives.

There are better regrets to avoid in life; the regret of a lost love, the regret of not reconciling with your parents, the regret of not having a child, or the regret of not tending to ones health.

I'm not exactly late in my career but having been doing this for ~7 years I'm not clear how people are able to accumulate the capital to start a business and have enough cash to live on until it makes money. It's something that seems like a great experience, and I can see myself wishing I had been able to, but I just don't know how I'd afford it.

Even assuming you have virtually no business expenses other than cloud hosting, are you just supposed to watch your emergency fund disappear?

I worked with a man who had done boring and lucrative government contracting, startups, tech companies, and self employment over a 35 year career. His last “job” is a startup. You always have choices. Especially if your skills are up to date.

I have started a few things with varying levels of success. I was looking at starting another thing, but instead decided to take a job with a not-for-profit. I don't regret the choice, because as a general rule I believe it's never too late to start something. I'll never stop having ideas, and given that we've had 250 years of technological and economic innovation, I think there will always be opportunities.

What I would regret is walking past a specific confluence of circumstances that seemed especially auspicious. It's sort of the inverse of my top reasons startups fail: https://www.quora.com/Startups/What-are-the-early-symptoms-t...

If this time I had found people I really wanted to work with, an idea that had promise, a market that we loved, etc, then I would be kicking myself for walking past that. At the end of the day, I ended up taking the path where I thought my next few years would have the most impact on the things I care about. I made the best decision I could with the facts I had. We'll see!

I started a business. Sold it for a couple years salary. Glad I did it. Don’t miss it.

My first internships were early-stage / startup type businesses, and the last decade+ of my tech career were at similar companies or businesses of my own. They gave me a wider array of experiences and a greater sense of personal control, but there's no doubt I would have made a lot more money elsewhere.

I wish in the early part of my career I would have not been so eager to get into startup / entrepreneurship land and had instead tried to get a few more "name brands" on my resume, for the experiences and contacts. That would have helped down the road.

I would actually spin this question back around on you: Now that you are in a later stage of your career, what's stopping you from starting something now? Don't ask if you will regret not doing it, figure out your plan and do it.

Honestly, don’t regret not starting a business. It’s about 1000 times harder than you think it is, despite all the glamor and wealth that 1% of the people achieve. Doing a startup takes a certain personality type. I am not that personality type. I joined a startup and saw the type of madness that was occurring and that made me understand how ill suited I was to start my own company.

My guess is that if you didn’t already start one at this point, you probably don’t have the proper personality type in the first place. Founders don’t need the opportunity, then just go for it, and it’s that type of spirit that keeps them going through all the ups and downs.

It isn't a binary question of "startup or not" - but always comes down to the specifics of what problem you wanted to solve, how you wanted to solve it, and all of the logistics (especially timing and team composition).

I am 50, my advice is don't fall into the trap that its either or. You can get a lot of signal without quitting your job. You can get a lot of work done by a $15/hour stay at home mom remotely. You don't have to risk it all. Once you are making money you can make the jump, or abort if it's not working. Just make sure your spouse is on board so there are no fights. If she is not (no sexism intended, I assume you are a man because women don't typically ask questions like this) then dont lose your marriage over it. That is a very real thing.

I think about this most days. The problem is that startups that fail put you very far behind relative to peers and the majority of startups fail.

It's fun, but it's also gambling with your financial future.

Have data on the opposite end: super stable type (Stanford MS&E undergrad; PhD track in ML 10+ years ago) who chose startups and entrepreneurship in scrappy, un-sexy niches of retail excess, operations research in shipping, etc., passing up opportunities in ibanking, hedge fund, and ML in Big Tech in the past ~15 years. My East Asian extended family was INCREDIBLY FRUSTRATED that I kept going off the beaten path and not following the "cultural formula" of good school->good role in company->seniority through years of service for a tried-and-true path forward... and they were right.

The EV of every path I've skipped was probably low eight figures by age 40 and more comfort/sanity, based on my friends/peers who went into them. Instead I have a semistable lifestyle business that I obsess over 24/7 and am constantly doing things outside my comfort zone, and while I make a reasonable amount there's a lot of business and inventory risk loaded in every step.

If I had a recommendation it would be this: instead of FOMO, collect a data point or two -- especially since you're implying that you're more steady-eddy and mature in your career path, switching to do a business for 2-3 years is super respectable and has very little downside since I imagine you have plenty of network and history to fall back to. Several of my friends in their 30s-40s have expressed a romanticized view of my career path to me, to which I bluntly say: this is mostly shit work that I suffer through to be consistent with identity and my values. It's got higher highs and WAY lower lows than your traditional 9-5, and I wouldn't wish this upon my enemies or friends. Do it only because you see unfilled needs and it bothers you so deeply that you gotta fix it on the market yourself.

There's a deep amount of glorification of entrepreneurship that's celebrated... and while I think everyone loves to see the journey, I honestly don't think most people would care for it themselves. To use an analogy: it's exhilarating to see an olympic gymnastic do her thing and push the limits of human possibility in 3-5 minutes on TV... but honestly, do most kids wanna practice 4-8 hours daily in a gym during your formative years of 8-18, obsessing over form and weight transfers and live with constant soreness and bodyaches while most people their age get to play videogames and gossip with friends and develop life their own way? Starting a business can have tradeoffs that feel similar -- for the brief moments of glory that are celebrated there's a lot of discomfort, monotony, suffering, and uncertainty that accompanies it that is rarely portrayed.

But simmer in that angst and FOMO... just realize you can use that as energy to get you to start down the path. Get a good advisor who's done it MULTIPLE TIMES BEFORE and hash out an MVP, and get the experience yourself before you figure out whether you want more. You're in a good position of having developed a long track record, so leverage your strengths and come collect a data point. :)