What no one talks about when running and selling a business

I've had the best year of my life post acquisition - spending more time with family, friends and thinking what's next. constantly thinking about what's next, it's actually annoying that I can't turn it off.

The "how much did you make" question is super annoying and it happens but generally those around me are respctful and understand that I still plan to work and in many ways will need to. Not enough to do nothing, enough to choose something meaningful and not waste our precious time.

My only advice to you is don't be afraid to reconnect with some old friends and embrace new ones, especially friends of friend who don't know much about your exit and ask to hang out with you because of who you are when they interact with you sans knowing your financial history.

What is challenging for me is the fact that most people cannot relate to my life. They can't understand why you'd work 60+ hours a week on a fledgling business. They can't understand the obsession and inability to "turn it off." They don't understand what it takes to get a customer to actually pay you, let alone build something people enjoy using and solves problems. I do find that many folks assume you just "lucked" your way in to success.

And I think bootstrapped business owners have it the worst of all. It's comparably easy to spend VC cash once you get funding, rather than money from "your own pocket." It's not hard to justify hiring 5 people when the VCs explicitly tell you that's what the money is for. Bootstrapping a successful business is indeed a rare feat, and only the people who've been there can understand exactly how all consuming and difficult it is. (At least, that's been my experience so far)

One of the unfortunate side effects of hustle/grit/what have you, that I myself experienced and can relate to the author.

My story:

For just about ever I have been a developer in the civilian world and an Army reservist. Normally the Army reserves thing is just a part time weekend gig doing some really boring administrative work, but sometimes its more.

The first time I was in management I was 24 years old. I hadn't finished my bachelor's degree yet. I was working as the tech lead of network operations in a group called TNOSC. This network, though, covered all of US and coalition forces in Kuwait, Iraq, and Afghanistan except for airport control systems.

This was in 2004 during the post-invasion surge into Iraq. I am not sure how many dedicated users I had (maybe 100,000) but there around 300,000 people who were impacted by my network between coalition military forces and supporting civilians. For perspective 300,000 is bigger than Google, Facebook, Microsoft, and Apple combined. In that management position I published the organization's taskorg (a diagram of who owns who plus the structure of our clients). We had two dedicated brigades to manage and my higher authority was CENTCOM with a dotted line to DISA. My clients were two 3-stars and a 4-star.

Running that organization was somewhat like running a start-up in reverse. We already had business and dedicate clients to support, but just jumping you are actually figure out the necessary relationships and how to do the technical aspects of your job. Life doesn't wait for you to catch up. You just have to figure everything out immediately.

In the real world I am software developer. I am not in management. I don't even bring up the prior military story. People simply cannot relate. They know the corporate world they are isolated into. In the civilian world you don't get magically dropped into that kind of position out of the blue.

Furthermore, people outside the military are more fragile. In the civilian world one of the most important interpersonal qualities is kindness while in the military kindness isn't valued. In the military kindness is like hard work. In most jobs nobody is rewarded for hard work. They are reward for what they accomplish. Hard work is silently implied. In the military what's important is honesty, respect (above and below), and bluntness.

I find in the corporate world I am constantly tempering my words and using my "inside voice" so that I don't come off as offensive. It is so easy to come off as an arrogant dick. People who have known me for a while or been through similar environments get it, but for everybody else its too easy to look like an asshole.

This is even more true in that I work as a web (JavaScript) developer. The most frequent kind of developer in the web are people who don't want to be there, have absolutely no regard for the technologies, and wish they were doing something else. The other extreme are immature childish developers who work in the web because it has a lower barrier to entry in the contributor roles require a large dose of abstractions and dependencies for every aspect of their job. Both of these groups are different shades of imposters who constantly live in fear that they will be discovered. Pro tip - Everybody knows who the imposters are. I sure as hell cannot relate my military experiences to these groups who hanging to their one and only career by their nails.

There are plenty of successful entrepreneurs that are perfectly capable of relating to others and treating their fellow men, friends and family with dignity and respect.

Some people succeed because they're playing nice with others, some succeed in spite of not being able to do so, some even succeed because they are are assholes.

There is no correlation here and you probably won't be able to extract many lessons from this piece, no one talks about it because it isn't a particularly common experience.

Wealth does not typically turn assholes in to non-assholes.

First I told him about survivorship bias and laid out basically the same statistics as in the article. Then I showed him that he could double his income in 3-5 years just by learning the craft of software engineering - risk free -- and still have plenty of time to enjoy his new marriage and enjoy his hobbies.

If his own company was struggling, he would be up late worrying about it. If the company he is working for is struggling and he keeps his skills up, he could easily get another job in our metro area. It's been that way for me for over 20 years.

I enjoy being a corporate drone, I go to work every day and leave the job at work -- and I'm a technical lead -- imagine how easy it is if you are "just" a senior developer? If you are a two income family in a good job market with one income as the average senior software engineer, you are guaranteed to be well within the top 10% of earners and be able to live a pretty good life.

Everybody says this, all the time. I would like to propose the controversial theory that actually material things do make people happy, at least within certain constraints.

When I was younger I had shitty cheap material things which made me unhappy. Now I have better stuff which makes me happier.

I used to have a shitty unairconditioned apartment. That made me unhappy. Now I have an apartment whose temperature isn't a problem.

I used to have cheap furniture, which was uncomfortable, and that made me unhappy. Now I have better furniture which is comfortable, I am happier.

I used to have a cheap unreliable car, which broke down and made me unhappy. Now I have a reliable, comfortable car I have no reason to be unhappy.

If you're a baseline-unhappy person (as I suspect the author is) then material goods are unlikely to improve your unhappiness. But I'm a baseline fairly happy person, I don't get unhappy unless there's a specific reason, like discomfort or inconvenience. Sensible acquisition of material goods can remove discomfort and inconvenience, thus making you happy.

That's a nice observation. Trying to prove you're the smartest person in the room during a casual social setting has to be one of the most irritating traits I can think of.

Anecdotal story: I was at a party and commented on a plane flying over us saying 'isn't it so cool something that big can fly?'. Someone drunkenly chimed in giving a 5 minute lecture on the physics of plane flight - an intentionally jargon-filled explanation at that. Everybody in the circle just walked away and 8 years later I still remember that as one of the most obnoxious things I've ever witnessed.

If you're an asshole without money, you're going to be an asshole when you have money, too. Money doesn't change you; it reveals you.

This is an interesting read, but the author spends way too much time defending his POV. He expects the people around him to just intuitively know what his skills are, but that isn't realistic. People can't know what you consider yourself to be good at unless you tell them.

The idea of a leader taking control of a 4 member band without consent is laughable. That is a dictator, not a leader.

It strikes me as interesting that I do not see this called out more in the comments.

Edit: Digging a bit further, it looks like the startup that he sold was Valet Gourmet which was a food delivery business in North Carolina and he worked on it for ~12 years. That's probably a bit longer than the tech startup timelines we tend to think of here.

You want to see some folks having fun or making music after an exit, talk to the horns or rhythm section.

Truth #3 — the skills that make you a good leader DO NOT transfer to social settings

For me it's the opposite. Learning how to network and interact honestly and with genuine care has completely reshaped my personality. I have such an easy time making friends these days and can, in a given, uncomfortable social interaction, easily distinguish between people being obnoxious and me being the one at fault (stepping over boundaries, being unreasonable, being superficial in my interaction). Ascribing "blame" properly saves you so much self-loathing and miscommunication. I have much greater control of my social life.

Truth #4 — the same charismatic attitude that makes you a good leader also makes you an asshole

Yes, and such is life. People will inevitably misunderstand you if they spend enough time focusing on you. There is an inherent imbalance in your relationship. My solution is to apologise when it comes up, and just always always greet people with respect (i hug) and leave them with respect (it was nice seeing you). Continual courtesy will override occasional mishaps, even the bad, drunken ones. Be honest about not being perfect, and show that you're trying.

Truth #5 — life post-exit is not all happy times

Very true. You really do need external confirmation in your life.

1. Help folks struggling to pay rent for a short while. Give them breathing room to get their lives on even keel. You have superhuman powers now. Use it. They'll be thankful. But don't expect anything back in return.

2. Start a soup kitchen in your local neighbourhood and get to know the folks. Each one of us is a Dostoyevski protagonist, swashbuckling hero waging war against our own crazy demons and wild fancy windmills. Ambition and its bitter outcomes are in all of us - not just "entrepreneurs".

3. "Soft adopt" a nephew/niece who is on the verge of falling into the deadly post teenage trap of feeling helpless, hopeless and depressed about their future. Some ideas: sponsor coding camps/programming classes, fund their college education or their sports interests. Encourage, encourage encourage. (Start with the worst off in the family. I am planning to adopt our 23-yo soon-to-be-full-drug-addict nephew unless someone intervenes. He's grown more despondent and depressed after dropping out of college. His troubled childhood and misery of coping with a broken family - parents are now effectively divorced has turned him into a lone outcast. I still remember holding him as a rugrat. I still believe we can cultivate a future he can be proud of.)

4. Lastly, simple thing: when folks invite you over for dinner or barbecues always insist on making the salad or dessert. Make it, don't buy it.

I think in the end you have to decide how you feel about compassion. There are some folks who have an absolute and resolute belief that compassion is a weakness of character. I personally believe compassion makes every one of us Superman.

The OP seems to learned how to be proven right. This may even be a driver of his success. Unfortunately the most of us do not like to be proven wrong all the time and feel offended by people like the OP. Looking at the comments this seems to be true also for the HN folks.

As with leadership skills, I think that enjoying to be a stay at home parent also must be learnt. It might seem hard, or boring, or tedious to some. But I am convinced basically anyone can make an enjoyable experience of it if they actually make an effort. It will not come automatically, it will take some time and effort.

Brutal truth to the author after having read the article is that he probably does qualify as being an asshole.

As a slight counterpoint to that though, despite what everyone says it is okay to be an asshole up to a certain point. It is better to just own up to it though than to deny it. This is advice from a self admitted asshole.

As for the money problem, you can avoid most of the problems by not mentioning your wealth to everyone and certainly by not showing it. Keep that for the closest of your bros, no further.

> Only 0.4% of all businesses make it to $10M in annual revenue. We made it almost halfway through...When I sold my startup, we had 100 people working with us.

> Unfortunately, I no longer have very many friends...

> ...Tesla...$300 pairs of jeans, $450 pairs of boots, concrete countertops...trips to New Zealand no longer bother me. That’s great and all, however ...you come across as a tone deaf asshole.

The only thing I look forward to is the next economic crisis; then maybe I'll be able to build something out of the rubble of other people's failures.

Economic stability is painful for me.

Occasional friction at work is expected, but when you are the leader by title, persuasion, expertise, and (best) because of "referent power," there are lots of ways to resolve conflicts over direction while preserving relationships. These methods often fail in relationships where the power structures are entirely different and have different bases. When you spend most of your time in one environment, it can be difficult to recognize that your skills don't translate to the other (social) environment.

In other words, if people sometimes think you're an asshole at work, the benefits of continuing the relationship often more easily outweigh the costs. The reverse is true in close personal relationships, where you're just an asshole. Then you either learn the different rules and accept that leadership is often much more subtle and soft, or you end up without friends and family.

And yes, money can change you for the worse, especially if you did not grow up with it. I have friends whom I discovered years later are third generation wealthy (9 figures) but basically live an upper middle class existence, minus the financial stress. I have other friends who were raised middle class and made a ton of money. They tend to be those complaining about people asking how much they've made.

It's the difference between living like Hyman Roth in the Godfather Part II, or living like Tony Montana in Scarface. If people are asking that, you're flashing too much. Either stop pimping your lifestyle, or stop worrying that people treat you like a pimp. Better yet, find a different class of people who also have money and won't ask. But the old money will still call you "noveau riche" for the remainder of your life.

Am I the only one who feels that those guys were judgmental assholes rather than the author?

HAHAHAHAHA! I laughed at this

The issue is that this guy is a jerk, that's all.

Sounds like he has taken becoming rich as a license to set his inner jerk free.

The equation of "employees" with "friends" here is a red flag for narcissism. It's possible to have friendly relationships with employees but that relationship is still primarily about exchanging services for compensation. As a result, the employees will put up with a lot more nonsense than any person whose livelihood is not directly dependent on keeping their boss happy.

E.g. "I feel like my opinion doesn't matter around him because I haven't made $1 mil" we'll if that's how you make people feel it's your fault... if they're simply insecure whiners it's your fault for keeping them in your life...

Same thing with friends...

Another area to improve would be a sense of style (no person with style buys $300 jeans, they're basically a product targeted at insecure nouveau riche... just shop at H&M)

... I guess the only reason this article is popular is that it comforts people who haven't made a million dollars that his life sucks too regardless...

And you have to possess certain qualities to succeed in that, which BTW work the best when you are not seeing part 1 as something bad at all.

This WILL make your social life a kind of hell - and you deserve it. People are not dumb customers, though not always able to articulate that (ie from shame, halo effect etc)

That's true whether or not your are successful.

In any case, the only people who are genuinely happy about your success are your parents.

Almost all of the examples of 'having a hard time around other people' amount to their self perceptions not necessarily the authors actions.

It's impossible to 'look at someone like a little girl'. It's mostly likely that these people either feel insecure, or, they project certain qualities upon the author.

I have a very 'straight face' and because of lack of emotional response, people have asked 'why am I angry at them?' when I had not even a whiff of such emotion. I was literally deeply contemplating what they were saying!

Now - it there may be other tons of behavioural signals - and it's possible the author was treating someone as a little girl, i.e. not paying attention, being dismissive, condescending without knowing it - which would then give a different characteristic to that persons opinion.

And it's easy for someone to create feelings when a successful person 'pulls up in a Tesla'. Any hint at bragging/humble-bragging in any way might be taken the wrong way.

But it's a good article, at least it's good to have some self-reflection/self-awareness.