Selling your company doesn’t make you happy

I've tried writing this comment multiple times and I'm struggling to find a way to explain it well. We sold our company[1] and part of the sale terms were we would be retained as the "managers" of the products (websites) and I always approached the sale as: "We take their money, they use their experience and assets to increase the value of the products and we continue to manage the product" and in theory that's what happened, unfortunately I made one big mistake: I didn't at any point realise how much control (freedom) mattered.<p>The company that acquired us is fine and I have no problems with them in any way and I enjoy my job, but it's just so different to how it was before. I guess a good real world comparison is renting vs. owning, if you own your home you can paint the walls, install a new floor or turn an entire wall into a television. When you're renting you're limited to very insignificant and inconsequential things, you can move around your sofas, have red plates instead of blue and get a new desk, but what sort of control is that? It's all cosmetic.<p>If I ever sell a company again I will absolutely make sure that the sale is the end of my involvement. If I wake up in the morning and have control I can think "today I'm going to make my company so fucking awesome, yeah!" because the sky is the limit, but as an employee it's just "oh, today I'm going to work... my goals are x and I can't change that" and when the former was previously possible and is no longer an option it's very depressing. I guess depressing is a dramatic word, but that's how it feels. Maybe stifling would be better, or trapped.<p>[1] I say company but the company was just for the sake of legalities, we didn't have an office or any formal structure, we just ran a couple of websites.<p>(I've been thinking about this for a while now and this blog post reminded me how I felt, sorry if the comment is too off-topic)

It depends on your circumstances, and specifically whether (a) running the company is what you most want to spend your time on and (b) whether you want liquidity and diversification.<p>I didn't want to spend my life running Viaweb, and I did want liquidity and diversification, so selling it made me very happy.

While I agree with the sentiment, the freedom provided by an exit (or alternately just a very profitable company) is certainly something that can make someone happy.<p>It isn't the 0's in the bank account, it's what they provide. It means you can work on bigger projects with more funding requirements. It means you don't ever have to worry about how the mortgage is getting paid next month, because you don't have one. It means you don't have to worry about how to get health care to take care or your aging parents, or how you are going to get your kids through college.<p>These are some of the biggest problems in life, and all of them go away with a big exit. Then you can spend your time focusing on the things that make you happy, which is probably for many of us building another company. The point is that it removes some stress and some worries, and that is a very good thing.

I built and sold a company last year. It was relatively small, but being able to go from an idea to acquisition in less than a year was incredibly validating to me, and that definitely made me happy.<p>Also, having extra cash in the bank means I have to worry less about how I'm going to pay rent this month, giving me more time to think about and do things that do make me happy, like spending time with family and friends, and making things.<p>Money can't buy you happiness, but it definitely doesn't hurt.

If you're a normal human being, you're likely to notice over time that the things that you think will make you happy, when they finally happen, don't. It's just something people are really bad at predicting.<p>If you're a normal human being, probably the only thing which actually makes you happy at the end of the day is helping somebody else selflessly-- best is if they don't even know it was you.<p>We're weird animals.

Selling for a good profit gives you the flexibility to do other things that you want to do, especially things that require capital, like starting a small team of devs and designers to work on another startup or creating a private space transport company.<p>So many artists around me would just love it if they could have even a marginal exit as to be artists all the time. However, most (as in, 99.9%) have to take a full-time job to make ends meet.<p>My point is not to say it's disingenuous to state that selling a company doesn't make a person happy. But I think one cannot underestimate how those finances helped to further happiness and even continued success.

There's another, very salient reason for selling your company. But only if you are a serial entreprenuer:<p>An exit validates your ability to build to sell and may move you ahead of the pack when a potential angel or VC calculates your probability for a successful exit, especially compared to others who are "unproven."

Related (from 2007 but still relevant!): <a href="http://www.erica.biz/2007/hitting-the-jackpot-doesnt-mean-instantly-becoming-happy/" rel="nofollow">http://www.erica.biz/2007/hitting-the-jackpot-doesnt-mean-in...</a><p>This does seem to be a consensus amongst successful entrepreneurs.

Paul Graham seems pretty happy doing Y Combinator, and what I've learned of him from the internet makes me think he's better off there than running the same company he started 'back in the day', both personally and in terms of what he's giving back to the world.

If you haven't already met your financial goals, then selling your company should help, and that should make you happy.<p>If you have met your financial goals, then the only reason to sell is if you aren't enjoying what you're doing or want to move on to other things. In which case selling gives you the freedom to do that.<p>It sounds like the author got a big pile of money and it didn't make him as happy as he thought it would. No surprise there, it's pretty well known that money doesn't buy happiness<i>.<p></i>Beyond about 75K/yr or so <a href="http://www.time.com/time/magazine/article/0,9171,2019628,00.html" rel="nofollow">http://www.time.com/time/magazine/article/0,9171,2019628,00....</a>

'The grass is always greener on the other side of the fence' is what my father always says.<p>He is a man who spent much of his youth traveling the world trying to 'find himself'. He ended up moving back to the same town he was born in.

Awesome post. Whether or not you'd like to sell a company for millions isn't the point - the point is that buckets of money won't make you happy, and it's really not what drives most successful entrepreneurs. Good entrepreneurs look at the money primarily as a scorecard and validation of their efforts and ideas. Is the money great? Sure. Does it buy some comforts and remove some stresses. Absolutely. But never mistake it for what really creates passion and happiness.<p>It's funny how as we grow we always move our bar and expectations. I remember when I first started my company, I thought "If only I had X orders and $X in revenue per month! I'd be set!"<p>Well, now I do have $X revenue. And I don't feel any different, just like he discusses. I simply have created a new "if I only" in my mind that drives me forward.<p>I think the trick is to continually be pushing forward toward growth and improvement while realizing that if you can't be happy with what you have, you likely won't be able to after a large, multi-million dollar exit.<p>Easier said than done, right?

All due respect Ryan, but were those life changing dollar amounts for the acquisitions? I seem to remember DropSend being sold on your blog, and Carsonified was a consulting company or something from what I can remember? Not to take anything away from your accomplishments and I 100% agree that money will never make you happy, but if you had gotten say $500 million from your acquisitions would the story be any different?

I might be late to this thread here but my question is: how do you go about selling your company for low 7 figures? I'm not asking how to make it worth that, my question is assuming that's a reasonable price for someone to buy your company for.<p>Do you mark it as for sale? Are they mostly private offers? Go through a broker?<p>Basically, I'm interested in how to actively put up for sale a company that is too big for something like flippa.com for instance

"Its true money can't buy you happiness. But it can buy you a big fucking yacht to pull up along side it."<p>-Diamond David Lee Roth

Going through "getting out" right now - essentially selling my chunk, but not sure what I like better: the uncertainty of a young startup or the stress of haggling with partners what my share should be worth.

I think people have come to undervalue proprietorship. In other times and places, it was/is a good thing just to have steady work as (say) an innkeeper. If we consider this as just an income stream, it's not much to strive for. If we want to be pointy-haired bosses, it seems pathetic. But a self-sustaining way of life offering some fulfillment is valuable, and not everyone can have a self-sustaining way of life where they order around lots of other people.

Selling OpenAir was a very positive experience. It gave me three things. A tremendous sense of accomplishment, financial security and most importantly the freedom to go back to the most exciting and difficult part of business, building startups from scratch.

Ryan, I would like to take your advice, but only for my second hypothetical company. I need the zeroes, even if they come with regrets. I can use some of the zeroes to start company 2, at which point I will start following your advice.

Again with these titles. speak for yourself.

Coming up to the end of several years of vesting after an acquisition. The acquiring company has been absolutely awesome and fun to work for, but its nothing like being in complete control of your destiny as a startup founder. You have a boss, you have smaller aspirations, its impossible to have as large an impact, and you have to push through lots of people to try new or risky things. The best you can hope for is a non-dysfunctional and creative organization, and I've been extremely lucky to have joined one. But I still miss the wild west of the scrappy startup phase, there really is nothing like it. PG's post about humans in their native habitat is spot on. You remember very quickly what it's like to be a caged animal when you are acquired.<p>That said, I think the author of this post is glossing over a major point.<p>When you're doing a startup in your 20s with essentially zero net worth, you're taking a massive risk. If you get sick, if your family members get sick, if you end up busting up your car, if your landlord throws you out, and so on, could all be complete disasters. Of course, you (generally) know this going into it but the reality is most young first time founders are dancing on the edge of disaster, on all fronts. (As I was) I know you're <i>supposed</i> to be financially secure before you start a company, but in practice this means 6-9 months of living expenses, and you still are one or, if you're very lucky, two disasters away from total ruin. If you want to be successful, you almost <i>have</i> to jump in when it feels dangerous to do so, because if you keep delaying for safety you'll never make the jump as your standard of living rises to meet your salary and so on.<p>Now, after an acquisition and the admittedly grueling process of going through a payout schedule, I am of the mindset that finally getting to a solid payout is going to be a life changing event for me. No, not because I will buy fancy cars or go on lavish vacations. In fact, I expect my standard of living to <i>decline</i> as the low-risk returns I expect to earn on my payout in the markets will result in a virtual "pay cut" for the time being as I prepare for the next adventure.<p>But what it <i>will</i> mean is I can have another thrilling startup experience (for all the reasons most people do it) without all of the truly scary, risky, life-endangering consequences. Sure, the startup can still fail and I can waste my time. Sure, I will still need to think frugally. But if disaster strikes, I (or my loved ones) won't end up bankrupt, on the streets, or dead. Also, until I jump back into the game again with a solid team and idea, I will be free to experiment and pursue where ever my curiosity leads me in finding that idea without the pressure cooker of "maybe I should start doing consulting again soon to pay the bills."<p>I haven't gotten quite to the finish line yet, but I have to imagine it will be a very liberating feeling, as long as I have a clear perspective on what exactly money can and cannot do for me, and how I should take advantage of the opportunity of having a few million in the bank. For me, its about freedom from having someone control my life, and removing the ambient risks life has without financial security, not about material things or indulgences. I'm so happy to live in a country where having one lucky break of an exit of a few million dollars can bring about this type of freedom if acted upon wisely.

Some people don't know how to retire.<p>Some people don't want to.

This article is out of touch with what it's like to not yet be a financially independent, respected, and successful entrepreneur.<p>Making a few million dollars, one path to which is selling a company, solves a huge number of problems. You stop worrying about making rent, take a year off and start something new without worrying about a paycheck, return to school to change careers without risk, have children and afford a babysitter, build the company you want to even if you don't have confidence it will succeed, hire a maid, have a lawyer do your taxes, have price insensitive vacations, wear fancy hats and expensive suites and deign to tell people how little difference money made in your life, ... shall I go on?