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 have a similar story. I let myself steer pretty far in the startup direction before I ultimately dropped those plans.
7 years later, I'm on a M&A team evaluating startups in the exact space I would have been in. There are many of them and few of us (companies looking to acquire). Most of them have failed or will fail and get nothing (beyond investment). The winner will get a mediocre payout that, for the founder, will merely compare to the salary I've earned in the meantime, if my back-of-the-envelope is correct. The stress, of course, will not compare. That's the reward for the winner.
> What I do regret is never finishing my side projects.
Just want to say I finally got out of that prison, and it's pretty nice. The trick for me was releasing way, way before I felt like I was ready. E.g., my little Twitter bot brings me a fair bit of pleasure: https://twitter.com/sfships
I actually had much bigger ambitions; the Twitter bot was my grudging compromise. I still hope to get to those bigger plans, but it's really satisfying to see actual people getting actual value. It's given me the energy to go back and productionize the infrastructure. Once that's done, I should be well placed to do a bit more.
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'd not suggest doing it on the fear of regret of not doing it
Second this. Don't start a company because you think it's "checking a box". It has to be something you can't imagine not doing, or else you're in for a world of hurt.
Also, unless you're going to be a one-person operation, it's a very serious responsibility. People will be affected by your hiring and firing decisions (and not just your employees, but those in their circle).
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.
This is so true. I've started a few startups and had a good acquisition. I've since made it one of my missions to espouse the underappreciated role that luck plays in a successful startup, and in life, in general.
You don't often hear it from people who have had the kind of success that leads them to being keynote speakers, I think, because everyone wants to feel like they deserve the success they've gotten. So, survivorship bias tends to kill this message. I think it's important, though, for people to understand when evaluating decisions (past, present, and future) and for learning from and empathizing with others.
Everyone likes to think of life as a meritocracy; that when you succeed it's because of the decisions you made and actions you executed. But people can make the right decisions for the wrong reasons, or vice versa. People can be prevented from making the decisions they'd like through no control of their own. And perhaps most significantly to the point, two different people can make the same decisions with different outcomes.
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.
One point I love about having many bosses is that the more numerous they are, the more you can get away with ignoring any single one. When I was consulting, I always tried to keep a few gigs going at different levels. That way if one client wanted something insane or dangerous, I could say, "Gosh, so busy!" and move along.
Paradoxically, having the ability to say no meant I didn't have to say it very much. When a client wanted something foolish, I could say confidently, "I don't think that's in your best interests," and explain why without fear.
This doesnt match my experience. Your users/clients are not bosses, they are optional. It's a qualitatively different experience from having "2 levels of bosses"
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.
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?
Bootstrapping is the magic word you are looking for.
Keep your day job, spend your nights and weekends working on your side hustle. Take the money from your day job and pay a developer to work on your side hustle while you work on the sales and marketing. Start making money on your side hustle and turn it into your day job.
Thank you, I'll google around for bootstrapping techniques going forward. Seems like one of those things where you need to know the right words to ask about or you have to really clumsily search around until someone tells you!
Of all my side projects, I've never thought of a way to monetize one. Would probably also be worth consulting an expert on that.
Build the absolutely smallest thing that someone will pay for. Keep adding features that customers ask for. Market every new feature. Reinvest everything you make back into the business. Don’t quit your day job until you have enough profits that it makes sense to go full time into your business
The solution for me was buying cheap houses in Detroit. For $30K you can buy a house that nets you $500 a month ($800/month rent minus expenses) so for example if you save $150K from your job that buys 5 houses yielding $2500 a month (or if you had $300K savings, $5K a month). That was the way I was able to replace at least part of my income and venture off to the land of not having a salary to free up time to pursue other projects.
That's a 20% yield if I'm not mistaken, there's got to be some catch to it.
Are those people renting a $30,000 house with $800 per month able to get banking services (and mortgages)? If not, I would feel like a dickensian landlord renting those houses to them.
Before we call Dave_TRS a slumlord, consider another perspective: The renter needs a home but can't afford the $30K to buy a house. $800 would be a basement apartment where I live, and about half the cost of what I hear studio apartments are going for in the nearest major city to my location. Dave_TRS is providing a service to the market at a price that isn't exploitative and the renter has a roof over the heads and everybody wins.
Even at a 10% interest rate and 0% down, a $30k mortgage is only $263/mo. This person is basically admitting that they are extracting value off the backs of the working poor due to unequal access to the banking system. I cannot imagine admitting being a slumlord on a public forum. And people wonder why people hate landlords.
If he got a loan, it wouldn't be 0% down because it would be on investment terms not residential terms. Chances are a $30K house needed improvement before it could be rented, and rentals are seldom free to run either -- there's ongoing maintenance, there's the carrying costs between tenants, etc. Calling the parent poster a slumlord without facts when your account is just a few hours old is pretty lame.
I wondered if there was a catch too so I started by buying one, and then expanding from there only after I saw it could work. It does feel strange buying the houses for so cheap, but I wouldn't say I feel any guilt or regret about the prices of the Detroit market. The price is what it is so I don't fault myself for getting a deal. As for $800 a month, for a freshly renovated 3 bedroom home I think the tenants aren't doing too badly either.
To the question about banking services, it's just not profitable to give mortgages on 30K homes for banks so they don't bother generally.
I have a business partner who is from Detroit (but doesn't live there), and still has some family there. So they are a fallback when there is a true emergency. For day to day property management and maintenance we have a network of contractors that we found on Craigslist or through referrals. Some of them stole from us or did bad work, but we didn't rehire, so eventually we developed strong relationships with reliable people.
I'd always wanted to take that risk and work on my own startup and I figured this was what was most likely to hold me back at some point.
Then I found myself in a situation where I had no girlfriend, my high paying finance job started to really suck cause my manager was a total idiot, and I was located in China which has an extremely vibrant entrepreneurial environment. I had quite a lot of savings by that time and living expenses are generally quite low in China. Also I was just a touch above 25 and young so I made the leap.
I guess I was luckier and can definitely appreciate it being harder the older you get and have no good answer to that. I can only imagine it'll get worse the longer you wait though. I think Musk said something along the lines of if you see yourself regretting it a few years down the line for not trying then just go for it
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.
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!
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.
Doing a startup takes luck. So much luck. Luck of birth, luck of everything going right, luck of meeting co founders, luck of circumstances being right to allow you to take risk. It's mostly just luck.
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.
> startups that fail put you very far behind relative to peers
I think this really depends on what metric you're using for success. If it's finances, a failed startup is almost certainly a significant setback. In terms of experience, that's much more debatable.
Believe me, finances is the metric of success for 95% of people and for the 5% where it isn’t they are either independently wealthy already or so delusional that failure is guaranteed.
Re: the inevitable "money isn't the metric of success" replies
You're not just saying that money isn't your metric of success, you are saying that nothing money can buy is your metric of success. Money can buy runway for your next startup, it can buy safety & security for your family, it can buy political influence, it can buy food for starving African children, and it can even buy time (shorter commutes and other peoples' time).
The world is full of people trying to convince you that making money for yourself shouldn't be a goal, but that helping them make money should be. These people don't ultimately care about money either, but they do care about something that money can buy, and they have internalized this fact.
If you truly don't care about anything that money can buy, all the power to you -- just please make sure you aren't being taken for a ride by someone using "money isn't the metric of success" to vampire your time and energy.
if no one did anything because they loved it, or because they thought it would help humankind, the world would be a much sadder and more transactional place. i dont know that we would have mathematicians, musicians, writers, costumers, chefs...or really much of anything
maybe just replace delusional with 'idealistic' or some other dismissive but less directly offensive term
Or maybe it's that many people who did those things and became successful with it are from privileged positions that allowed them to do such things...
And so if we lifted people into positions where they didn't feel like their basic needs would be taken away if they didn't work some job making money then they could experiment and do things that were less transactional... But until we have that Star Trek future - we gonna be transactional.
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. :)
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.