Ask HN: Founders who sold their company, what do you do? - PirxThePilot
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Joe8Bit
Exited with two co-founders when our runway ran out. Sold our IP and assets
for a modest amount to our main competitor.

I realised that (as CTO) the main area I couldn't contribute to was 'the
business' of running a successful company. So I decided to remedy that, I
joined McKinsey and left last year as an Associate Partner. I'm now the VP
Engineering at a fast growing tech company (250+ people) and the impact I can
have with technology is an order of magnitude greater than before because of
the intervening experience

~~~
123ol12313
Can you explain a little about how your experience at McKinsey has allowed you
to have a greater impact? Why did you go back to VP Engineering after having
consulting experience? At first though, I would think your technology
experience would give you leverage on the business side rather than the other
way around.

~~~
Joe8Bit
Among many other things the experience gave me:

* Empathy with the folks who's thinking was alien to me previously. I learned through doing their job. I could communicate with them and work in their context in a way that allows me much more leverage and ability to have impact with engineering.

* I learned the semantics and pragmatics of running a large organisation which gave me the lexicon and confidence to be taken seriously doing it (therefore more leverage) and taught me lots of small but important tactical lessons (e.g. how to manage difficult shareholders)

* How to communicate complex technical subjects to people who either don't/can't/won't understand them.

* A HUGE network

I went back because I missed it. I wanted to do consulting as a way of getting
better at being an engineering leader, not leaving it forever. I was offered a
few things at VC/PE firms, or in typical 'business' roles, but none of them
really appealed. Not my passion.

~~~
karambahh
Thanks for your insights.

I had never thought of the big 3 as possible route post-sale. Sale is not on
the radar atm so back to my daily operational duties in my small yet thriving
company :-)

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kp02
Sold last year (2 founders) to a very focused private equity fund from a weak
position - We were bootstrapped and profitable but large competitors entered
the space and we were slowly losing the battle.

From financial perspective it was personally a good deal. Now have a 3-year
non-compete for a specific field. The new owner is doing well with a larger
team, resources and synergies between their other investments.

One aspect that's not very often covered is the psychological side which was
very hard for me. Soon after closing and moving forward, I absolutely felt
lost, more than ever before - Kind of lost my purpose? No customers to care
about, weaker connection with earlier team mates and professional friends from
the industry, a lot of free time and no hecticness I used to have.

Started working on something new, validated and built the 1st version of the
product, got very light traction but didn't find a profitable model for it.
Had investment offers on table to get funded but declined as we were not
confident about the business case.

Now investing slowly, doing the things I like more intensively (skiing &
climbing) and trying to understand what would the next
professional/entrepreneurial step be and what I want in life.

~~~
japhyr
How hard is it to build something new while under a non-compete?

I understand you can find new areas to work in, but I imagine you'd think back
to previous work and be tempted to make connections to that field, or use some
of what you built previously in the new context.

Is it difficult, or is it just a completely separate problem space?

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corbett3000
I sold my 10 year old company about a year ago and promoted my #2 to CEO to
lead it post acquisition. Aside from the company related responsibilities I
still have here's what I've been doing:

-Actively working to strip away the identity/persona I built up over the last decade while leading the company, in order to get back to "who I really am and/or accurately understand who I've become" outside of the context of the company and the role of CEO/Founder.

-Reading SO MUCH. And specifically the book "The Adult Years" has been essential for me in understanding the life stages we all go through and how to manage transition best.

-Going on extreme/esoteric retreats: like climbing a snowy mountain this winter in Poland in just a bathing suit. I'm trying to push myself physically in ways I've never done before.

-Bought a house for the first time and am learning to be a DIY god.

-Supporting my wife's entrepreneurial journey as much as possible (she's the founder of her own successful company).

-Being open again to mentoring/supporting others as much as possible.

-I hope to soon become a Court Appointed Advocate so I can help NYC area kids who are caught up in "the system" in some way shape or form.

-Oh and...lot of financial/estate planning work :)

~~~
badpun
> Going on extreme/esoteric retreats: like climbing a snowy mountain this
> winter in Poland in just a bathing suit. I'm trying to push myself
> physically in ways I've never done before.

I don't know how tall or remote was this mountain, but a guy I know nearly
died (well, technically he was dead for a bit while they reanimated him on the
rescue helicopter) running in Polish mountains last winter without a proper
clothing.

~~~
corbett3000
Wow. Um...what was his medical condition?

~~~
badpun
It's hard to tell what really happened, as he has no recollection of the time
before the accident. The rescue party, alarmed by his wife, found him laying
on the trail, unconscious and in severe hypothermia. The thing is, while he
was running in his relatively light running clothes (the whole run was
supposed to take only 40 minutes), the weather suddently turned for the worse,
with temperature drop and snow fall. Hard to tell if he lost consciousness
just because of the cold or if something else was also a factor.

------
lazyjones
Solo founder (with VC), sold after 15 years (last 13 highly profitable).

Good question. Trying to invest carefully, enjoy life and undo the damage
entrepreneurship did to my friendships, hobbies... No 40+ hours/week jobs any
more, thank you.

~~~
ksec
How do you "Undo" the damage? Really interested in that part.

You dont have to be an entrepreneur to be super busy. Some part of the world
expect you to work at at least 80 hours a week. So i guess this is good for
everyone to know.

*As you grew older, you came to realise how little money actually means.

~~~
lazyjones
> _How do you "Undo" the damage? Really interested in that part._

Lost time is lost, but you can get in touch with old friends, apologise to
people you ignored because you were busy, find new hobbies, travel... At least
that's what I'm trying to do. I also lost 2 close family members during that
time and deeply regret not having spent more time with them, but that's just
how it is.

> _As you grew older, you came to realise how little money actually means._

I'd still disagree, it means a lot and makes life so much easier. It's just
something you tend to take for granted when you have it and other things you
don't naturally become more important.

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hopfog
I sold my company last year and the deal came with a standard lock-up period.
The company that bought us has a really bright future and I'm excited to be
part of their journey so I don't mind.

I'm currently working hard on integrating the product into their portfolio.
Since they are using our former company as a stepping stone into a new market
it's a lot like running a startup again, just with much more capital and
people.

~~~
solarkraft
Sounds pretty fun! Are you still working as much as before?

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cthulhuology
First company I sold... paid off student loans, traveled around for a year....
then started a consultancy..

Second company I sold... invested in a friend's business (she's now my wife),
self funded another business (that one failed to find a buyer).... went back
to work...

Third company I sold... paid down mortgages, put kids into private schools,
fixed up house, self funded another business ( currently a going concern,
break even)...

What do I do now? Keep working... started a new businesses and handed off day
to day operations to my business partner, and am now taking a new job so I can
move to Europe.

What do I plan to do in the future... same thing, keep working, looking for
interesting projects, probably start more business.

~~~
maxwin
invested in a friend's business (she's now my wife) --> Best ROI lol

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superplussed
I played professional poker for 3-4 years after selling my first startup in
2007. In hindsight I should have jumped straight back into tech, but I was
seriously burned out and the poker monies was good.

~~~
downandout
_> The poker monies was good._

Would you mind sharing round figures? I've always wondered how much pro poker
players that don't have endorsements etc. actually manage to scrape away from
the game after rake, travel expenses, leaks (pit games), etc.

~~~
superplussed
I made 90% of my winnings online, and treated live tournies and cash games as
kind of a break from my real job. I was a heads up specialist (we used to be
referred in a derogatory sense as "bum-hunters") who could enjoy basically
variance-free winnings if you were table selecting well enough. So my winnings
were comfortably in the 6 figures each year pre-tax, until Black Friday hit
and it all came crashing down.

~~~
unwind
If (like me) you don't know anything about the (online) poker scene, "Black
Friday" here is likely a reference to United States v. Scheinberg [1], a
federal criminal case against the founders of some major online poker sites.

[1]
[https://en.wikipedia.org/wiki/United_States_v._Scheinberg](https://en.wikipedia.org/wiki/United_States_v._Scheinberg)

~~~
teddyuk
out of interest, do the people of the usa generally agree that gambling like
this should still be illegal (especially when most other countries allow it?).

i'm in the uk and gambling is allowed.

~~~
Retric
People are going to be all over the map on this one. I see large downsides and
minimal upsides to online gambling.

I think it should be illegal in practice because people get into massive
downward spirals. Now, that does not mean we need no ban ultra low stakes
poker, just the kind of games that cause people to go broke. Aka, someone that
loses 200$ a month on poker is not a big deal. Someone that's losing 20,000+$
/ month is likely a different story.

I have similar issues with the App Store and feel Apple / Google should limit
in app purchases per month.

~~~
majani
It's trivial for gamblers to get round such a regulation and trivial for
bookies to plausibly deny it

~~~
Retric
You can say the same thing about DRM, but even 98% effective is good enough to
be very useful. It's the same reason you can't buy lotto tickets with a credit
card even if credit cards let you get cash advances that's an extra step that
really makes a meaningful difference in people's lives.

------
acqthrowaway
We sold to one of the mega tech companies a couple of years ago. I'm still at
the company as an engineering manager. I haven't decided what I want to do
next and there's still some time until my golden handcuffs expire.

~~~
dsign
If you don't mind to share, how long are your "golden handcuffs"? I'm quite
fearful of those....

~~~
SOLAR_FIELDS
Anecdotally what I typically see is a big chunk of change over 4-5 years and
then smaller chunks every year to extend the handcuffs. YMMV

~~~
dsign
It's quite a long time ... I guess many entrepreneurs just want to move on and
hate being on the "you are behold to us" part of the acquisition...

~~~
dagw
I can kind of understand both sides. Company I used to work for bought up a
small company to expand their product portfolio. I don't know the details, but
the acquired company was never really happy with their new life and 2-3 years
later almost everybody from that acquisition had left (and taken some of their
new colleagues with them) and there was no one left in the company that could
really continue the work they'd been doing. Basically 3-4 years later it was
as if the acquisition had never taken place

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justanon1234wh
I'll do a throwaway for this. Company had an exit that was about $120m
personally for me about 3 years ago. It was a hard slog of about 14 years
during which time me and my cofounders got sick of each other, most
relationships that I came in with blew up and so on.

It is so very strange to not work. First off, everyone all the time is lightly
nagging you to work. I don't want to work! I already did that. Surprisingly it
is my retired parents who nag the least since they understand retirement the
best. It's everyone else my own age (35) that is weird. People who lightly
know you ask 100 questions and you sort of have to lie or carefully select
truths when you first meet someone because it goes badly saying what you
really think most days. Some variation on "Don't you get bored?" constantly
coming up. Answer is - no!

After a few years of this lifestyle I am settled in quite nicely and almost
don't remember working except as a distant other life. I work out, I see
friends, I go drinking, I get up at 7am, I read Hacker News, I do a hobby here
and there. Any time I throw myself into a hobby I typically find it fills 2-3
hours a day that is just about enough time in a day to be busy for me
nowadays.

One thing that definitely differentiates is I can travel and do the hobbies of
a rich person. I rarely get to throw around numbers with strangers so almost
weird to even type but I am spending $2.4m this year just on my little pet
projects. Not businesses - just stuff I wanna do for fun with no real purpose.

I am very serious about managing my money and I'm a wealth manager's worst
nightmare. I meet with everyone, talk endlessly about what is possible, read a
lot on investment, and very very rarely give people my business. They are
welcome to pitch but after meeting with a ton of folks I ended up making it my
part time job and I always know more than the back slapping sales guys they
send to try and get 1% fees out of me.

You end up finding other people in similar situations. I have a good friend
from my startup days in a similar boat with a slightly lower number who made
$8m on crypto this year purely out of boredom. He made $10m the year before on
a startup he cofounded for 18 months again out of boredom. We get together
every week or two, talk about the struggle to keep busy but not too busy. Ha
it sounds like we are complaining! It's just a balance as we navigate having
fun with projects but not getting stuck in a decade long slog again.

I guess I like the idea of being 'rich uncle' or 'grandpa' to a startup,
having a flexible amount of involvement. Perhaps daily for 6 months, 4 days a
week for a year more, and then 1 day a week from there. In the real world I
just worry I'd be so involved it would accidentally be me killing myself and
stressing out for 7 years to build a $20m company when my investments make me
$7 a year living my life with freedom.

Dating is a bit funny when you don't work; you sort of self-select the people
for whom it is an issue. People see my house at some point in the dating cycle
and there's no hiding the situation. I have on a whim with 24 hours notice
taken a girl I was attracted to across the world, had a great week, and then
basically that was it. But by and large dating is just normal go around have
dinner get a drink stuff, no helicopter sunset champagne yacht adventures. I
feel a little bad I'm doing it wrong. Very few gold diggers in my life,
surprisingly. I kind of was hoping at one point my friends would have to tear
me off of some model. Ah well. I watch TV shows like Ballers and their idea of
what rich people are like is really funny to me; I do normal things and date
normal people. I suspect based on dating history I'm going to become a stay at
home dad to a career minded woman. I suspect it is rewarding to raise the
kids?

~~~
Ionis75
That lifestyle sounds amazing coming from a late 20 year old. Hoping I can
achieve that in the next 5 years too :)

What was the company specializing in that you co-founded?

~~~
justanon1234wh
Good luck! It was a stunningly unremarkable software company that never makes
it on Hacker News. Slogged it out, bunch of false starts, ended up going
pretty well after a rough first year where it almost blew up and a really
rough fifth year where it again almost blew up.

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csallen
Still working on it post-sale, but with more resources at my disposal and a
sturdy safety net to prevent abject failure due to lack of resources.

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vinrob92
I sold part of my online letting agency for a small amount of €€€ and now
running another company while being a DN in Asia :)

~~~
dmtzz
Mind me asking, what does DN mean?

~~~
cperciva
I'm guessing Digital Nomad.

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majani
Bought it back :)

~~~
solarkraft
Why, how and how did it work out? Would read an entire blog post about it.

~~~
majani
OK then, read this :) [http://www.techweez.com/2017/06/05/majani-speaks-on-
ghafla-a...](http://www.techweez.com/2017/06/05/majani-speaks-on-ghafla-
acquisition-fail/)

------
rasengan
I started more companies and work even harder now. What is the point of doing
anything other than what you love?

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throwaway877544
The startup nearly killed me but I cashed out ~$3M after taxes. It’s all
invested in a portfolio of index funds.

I moved to a ski town in Colorado and ski 3x per week and volunteer teach
fitness classes 4x per week.

My wife and I have plenty of time and money so we “live sexy” - basically
we’re swingers. We try to hook up with others for a threesome our foursome
once a month or so. It is insanely fun but only works because we have a super
strong relationship.

Hooking up with others has been great motivation to stay healthy. I live close
to the main street in our town and walk to the grocery store most days for
lunch. I’m in the best physical shape of my life.

I sleep on average 9 hours a night. If I ever feel at all in a negative mood I
take a nap and feel great again.

I stay lightly in the entrepreneurial game but don’t do anything that demands
much of my time. Working ~20 hours a week I’ll do ~$100k in profits.

My wife and I talk a lot about how we’re basically cheating at life because
money isn’t supposed to buy happiness but in our case it definitely has!

~~~
sigi45
Always interesting to see what other people think is 'cool'.

I love my wife too much to swing. Couldn't and don't want to imagine someone
else having sex with my wife.

~~~
throwaway877544
We mostly do FFM threesomes and soft swap (oral only) in larger group
situations. She’s just not that interested in other guys, moreso the ladies,
which works for me.

I like to see her happy. She likes to see me happy. The dynamic obviously
isn’t for everyone but it works for us.

~~~
sigi45
Would it work the other way around also? Would it be okay for you to do FMM?

Independend of my wifes choice of doing ffm, i will not do this until i'm
compftable with fmm and i'm not. I don't even care for ffm or fmm very much
anyway but fmm is the deal breaker for ffm.

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erikb
I haven't succeeded in that area yet. But here's what I would do: I'd get a
job for about 20h/week as a developer because I like developing. I'd charge a
rather low pay and make sure already in the interview that the boss knows I
can leave any time if he pisses me off too much. Reason being that without a
regular main task and daily interaction with the same people even the biggest
loner feels lonely and useless.

Then I would spend a lot of time travelling, prepping travels, honing my
hobbies, and probably I would also make investing more of a hobby. I expect
it's good to see the effort and ambition of other people succeeding, even if
one is only passively involved in what they are doing.

Last but not least: I hope you ask this question before you succeeded
financially. In the big topics in life one should have at least a broad idea
what one wants to do before huge failures or huge successes are incoming.

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jirenandcell
Congratulations on your success!. Just wondering - How old were you when you
started your company,what would you do differently when starting another
company and the market that you were in, was a large one or a niche?

