[HN Gopher] Lessons from my first exit
       ___________________________________________________________________
        
       Lessons from my first exit
        
       Author : saeedesmaili
       Score  : 321 points
       Date   : 2024-11-14 07:32 UTC (15 hours ago)
        
 (HTM) web link (mtlynch.io)
 (TXT) w3m dump (mtlynch.io)
        
       | akoboldfrying wrote:
       | Absolute gold for any founder or would-be founder, as are all his
       | posts on TinyPilot and his other web businesses. Raw numbers and
       | transparency abound, and the overall tone is that of a well-
       | organised, fair-minded person.
        
         | optymizer wrote:
         | Agreed. I saved it in case it goes offline, for when I'll need
         | to sell my future business, if I ever start one.
        
       | garyclarke27 wrote:
       | Nice writeup - Wow your broker fee was crazy high 15%. I paid 3%
       | when I sold a $5M business in the UK.
        
         | vdvsvwvwvwvwv wrote:
         | So your fee was higher
        
       | adwn wrote:
       | > _I had a dedicated TinyPilot GCP project, but it was within my
       | personal Google account._
       | 
       | This sounds crazy to me. Never ever mix your business and
       | personal accounts _for anything_! The point of an LLC (in any
       | jurisdiction) is to keep your personal and business concerns
       | separate, so why would you break that rule for Google? Which is
       | why my reaction to these lines:
       | 
       | > _I always sent emails related to the business from my
       | @tinypilotkvm.com email address._
       | 
       | > _I always used @tinypilotkvm.com email addresses whenever
       | signing up for services on behalf of TinyPilot._
       | 
       | was along the lines of "Well, DUH!" Of course, that's the first
       | thing you do with a new business: dedicated bank account,
       | dedicated email address.
        
         | anonzzzies wrote:
         | I don't know which project is going to make it and which is
         | not; will be very painful opening companies for all of these.
         | So I open one once something is doing $5k+/mo only.
        
           | adwn wrote:
           | That doesn't really contradict my point. Create separate
           | accounts _as soon as you open a business_ , not as as soon as
           | you create a new directory under _~ /projects/_.
        
             | anonzzzies wrote:
             | Yeah, so my entries under ~/projects are 'new' until
             | $5k/mo, so that works.
        
           | eadmund wrote:
           | The pain and cost very much depend on one's jurisdiction
           | (hey, once upon a time it literally required an act of
           | Parliament!). And there are levels to it, too. Absolutely,
           | the first time one sets up a company one needs to hire a
           | lawyer. But after that it's more of a judgment call.
           | 
           | $5k/month is $60k/year -- I am not myself comfortable with
           | the unlimited personal liability risk that brings without a
           | company.
        
             | anonzzzies wrote:
             | > $5k/month is $60k/year -- I am not myself comfortable
             | with the unlimited personal liability risk that brings
             | without a company.
             | 
             | Yeah, here that's not such a problem; I wouldn't do a LLC
             | at all if it would not really help with selling it.
        
           | croisillon wrote:
           | if you have a couple projects making a couple thousands a
           | months, you could still open one company to manage those
           | projects
        
         | gizzlon wrote:
         | Regarding GCP migration: I would just add the new account(s) as
         | Owner to every relevant project. Then they can remove you after
         | the 30 days or whenever they're comfortable.
        
         | mtlynch wrote:
         | Author here. Thanks for reading.
         | 
         | > _This sounds crazy to me. Never ever mix your business and
         | personal accounts for anything! The point of an LLC (in any
         | jurisdiction) is to keep your personal and business concerns
         | separate, so why would you break that rule for Google?_
         | 
         | The finances were always separate. The company GCP project was
         | on a dedicated billing account within GCP, so I don't think it
         | violated any rules about business/personal separation of an
         | LLC.
         | 
         | > _was along the lines of "Well, DUH!" Of course, that's the
         | first thing you do with a new business: dedicated bank account,
         | dedicated email address._
         | 
         | Dedicated email address: yes.
         | 
         | Dedicated bank account: no, not from the start.
         | 
         | What bank do you use that will give you a dedicated account for
         | every business idea you have before you even know if it will
         | materialize into something?
         | 
         | I have a business checking account under my sole proprietorship
         | before I know if the business will turn into anything. A few
         | months into TinyPilot, I registered an LLC and created
         | dedicated bank accounts at that point.
         | 
         | But there's so much work and friction in opening a business
         | bank account in the US that I couldn't possibly do it as soon
         | as I have the idea for the business. I had ~10 other businesses
         | that flopped before TinyPilot. It's impractical to have
         | dedicated bank accounts for each one ready to go on day one.
         | And registering an LLC is ~$600 all-in plus a few hundred in
         | yearly renewals, plus $200 to shut it down.
        
       | anonzzzies wrote:
       | People use a broker for these amounts? I did a bunch of sales
       | around 1m$ just with escrow myself. But that was a while ago; is
       | it the norm or?
        
         | rodrigobellusci wrote:
         | He explains that the broker found a buyer he couldn't have
         | found by himself. If I recall correctly he had looked for
         | buyers but none had met his criteria.
        
         | maxresdefault wrote:
         | For what line of business? Were there multiple smaller sales
         | totaling 1m$ or multiple 1m$ sales?
        
       | ffjffsfr wrote:
       | great write up.
       | 
       | > $920k over four years
       | 
       | so this gives an average yearly salary of 230k. Very close to
       | FAANG senior salary with much more risk, effort and (probably)
       | worse life-work balance. OP quit from google in 2018 and ran some
       | other business, and this is his biggest sale so far. I think it
       | shows how hard it is to make better money outside FAANG even when
       | extremely talented and lucky like OP. But it's probably more
       | about lifestyle choices.
        
         | ragnot wrote:
         | Kinda sobering when you think about it.
        
         | deadbabe wrote:
         | It's not worth it. Neither is freelancing. One of the appeals
         | of freelancing was being able to work from anywhere in the
         | world and still make money, but with wider availability of
         | remote jobs that advantage evaporates.
         | 
         | Working for a good company is still the best most consistent
         | way to make good money and have a good life.
        
           | fragmede wrote:
           | How many companies let you work 3 days a week? Not from home,
           | just three days a week aka5 day weekends every week?
        
             | deadbabe wrote:
             | Depends. Are we talking hours? Because if so, then most
             | companies barely give 2 days worth of work per week. And in
             | many cases, people probably work half of that, maybe 4 or 5
             | hours of actual focused work per day.
             | 
             | A freelancer spending very little time working probably
             | isn't making much money. But an employee who spends little
             | time working, is still bringing in those same paychecks,
             | week after week.
        
         | tempworkac wrote:
         | interesting to reconcile this with calls to tax the rich. maybe
         | we should be rewarding such effort after all? think about the
         | tens of thousands of jobs created from people working at Google
         | who'd make L3 or less at Google working twice as much...
        
           | dkdbejwi383 wrote:
           | I'm not sure I follow what you're saying. People who work at
           | Google should pay more/less tax? Or that people who start
           | companies should get more tax breaks (or pay more?)
           | 
           | I'm European so I don't really click with the obsession some
           | places have with avoiding tax, so you may have to explain it
           | like I'm 5 :-)
        
             | thrw42A8N wrote:
             | Lol, Europe is the home and crown palace of tax evasion,
             | look to the Netherlands, Ireland, Switzerland,
             | Liechtenstein, Andorra, Gibraltar, Isle of Man, Jersey...
        
           | qzw wrote:
           | Speaking as a small business owner/entrepreneur myself, there
           | are lots of tax deductions available to people like me that
           | aren't to some collecting a salary. And that's without doing
           | any of the borderline or outright illegal stuff that I see
           | many other business owners do, such as taking fancy
           | vacations, leasing luxury cars, or buying real estate for
           | personal use but writing them off as business expenses. The
           | IRS basically now lacks the resources to go after most such
           | cases, and even if they're caught, the penalty often just
           | amounts to paying back the avoided taxes. There's really very
           | little incentive to play by the rules. I've had CPAs tell me
           | outright that I'm leaving money on the table by not using
           | some of these so-called tax minimization strategies. Anyway,
           | it's all kind of beside the point because "tax the rich" as
           | policy covers so much ground that it's impossible to discuss
           | the pros and cons without specifying what specific proposal
           | we're talking about. My point is simply that business
           | ownership and entrepreneurial activity are already quite well
           | incentivized/rewarded by the current tax code.
        
             | hartator wrote:
             | What are these miraculous tax deductions you are talking
             | about?
             | 
             | Writing personal expenses as business expenses is tax
             | fraud, not tax optimization. CPA suggesting this should be
             | fired.
        
               | hash872 wrote:
               | 1. The Trump era automatic 20% deduction for LLC or
               | corporate income. Totally unjustifiable, it's 20% off
               | your revenue for everyone with a company for no public
               | policy reason that I know of 2. You can mostly avoid
               | paying into SS/Medicare by taking the large majority of
               | your compensation via distributions, not salaried income
               | 
               | Just off the top of my head
        
               | hartator wrote:
               | You mean QBI? To apply, it needs to be matched with W-2
               | wages so you won't escape SS/Medicare, and it's not
               | against revenue but profit.
        
               | qzw wrote:
               | It encourages paying more wages, but it's still a 20%
               | giveaway to the business owners for _paying themselves_.
               | I know that my own effective tax rate went down a couple
               | percent when QBI took effect. If the idea behind the
               | requirement to pay reasonable wages is to get more SS
               | /Medicare tax revenue, then QBI more than offsets any
               | gains. Plus the business owner can tweak their own
               | numbers to determine what's the most advantageous mix of
               | W-2 vs K-1 income. It's another advantage not available
               | to regular wage earners.
        
               | schmidtleonard wrote:
               | Should be but won't be.
               | 
               | I can also attest that in my local small business
               | community I have been met with puzzlement and suspicion
               | for not engaging in expense fraud and PPP fraud.
               | Deviation is almost completely normalized.
        
               | qzw wrote:
               | Of course it's against the law, and so is not obeying the
               | speed limit. And both are being done every day widely and
               | more or less blatantly with little to no chance for
               | consequence. In fact you're probably more likely to get a
               | speeding ticket than to be audited. Hence the CPAs who
               | would recommend some of these "strategies" as long as
               | there's even the slightest plausible justification,
               | because in their experience there's very little risk for
               | pushing the envelope.
        
               | stanford_labrat wrote:
               | my very first exposure to this was paying for parking. i
               | worked at a large private university which had a
               | beautiful but very big campus. ofc for some reason the
               | institution decided that employee's had to pay for their
               | own parking, which i disagreed with on moral grounds and
               | the fact that parking was so far away it was like a 20
               | minute walk just to get to my work space...so i did an
               | experiment where i basically never paid for parking in my
               | entire 4 years there.
               | 
               | it would have cost me about 2 grand to diligently pay for
               | parking. the actual expense from tickets? about 100 bucks
               | maybe 200. and some of them got automatically thrown out
               | just by challenging them. now towards the end of my time
               | there i did see a guy get towed as he was walking up to
               | his car. i started paying for parking then.
        
               | rurp wrote:
               | Interesting, I had the exact opposite experience as a
               | student at a public university in California. There were
               | meter maids patrolling the parking lots _constantly_ ,
               | and it was common for people to be ticketed within
               | minutes. It must have been a huge revenue driver for the
               | school. The enforcers were so zealous I received multiple
               | tickets despite having a valid annual pass displayed
               | clearly in my window, which I then had to burn time
               | fighting to get dismissed.
        
           | Eridrus wrote:
           | There is already a very big tax break for entrepreneurs:
           | QSBS.
           | 
           | You have to stick it out for 5 years (the rollover provisions
           | are not well aligned with SAFEs), but all your capital gains
           | are tax free up to $10m.
           | 
           | Reforming the rollover provisions or making it not a hard cut
           | off would certainly be helpful though.
        
           | sharemywin wrote:
           | we go into debt 2T every year without the extra money I would
           | argue a lot of the nice to haves get cut from people's
           | budgets.
           | 
           | where do you think Netflix and google ads fit in Maslow's
           | hierarchy of needs?
           | 
           | Also, big tech had a huge amount of jobs cuts recently.
        
         | antupis wrote:
         | A big part is that you are not working for man but yourself.
        
           | pfarrell wrote:
           | Don't forget your investors and your board.
        
             | kfrane wrote:
             | It's a bootstrapped business, no investors/board.
        
         | yen223 wrote:
         | It's not quite apples-to-oranges, because he started a hardware
         | company, which historically has much smaller margins than
         | software.
         | 
         | The difference isn't just working for FAANG vs running a
         | business, the difference is also working in software vs working
         | in hardware.
        
           | lokimedes wrote:
           | The difference is working for yourself. It's the business
           | version of achieving adulthood (for some).
        
         | rco8786 wrote:
         | > Very close to FAANG senior salary
         | 
         | Base salary maybe. But more like ~40% of FAANG TC. (Which only
         | furthers your point)
        
         | ericjmorey wrote:
         | High risk activities are never going to be accurately
         | represented by a single data point.
        
           | sharemywin wrote:
           | good point it's the 99 out of 100 cases that fail miserably
           | that more accurately reflects expected value.
        
             | riku_iki wrote:
             | Sure, its educated gambling, but it is not fair to exclude
             | high value exits too.
        
               | toomuchtodo wrote:
               | It is when they're effectively lottery tickets.
        
         | optymizer wrote:
         | Senior devs are closer to 400K-500K total comp. Very senior
         | devs are above that.
         | 
         | Still, the value of working on your own project full-time
         | (rather than someone else's thing) can easily justify accepting
         | the difference.
        
           | yen223 wrote:
           | I'm surprised no one here has factored in the very real risk
           | of getting laid off.
        
             | negus wrote:
             | Do you think that this risk is bigger than you business
             | being hit by the market?
        
               | yen223 wrote:
               | Probably not, but it's still not 0
        
         | throwaway23453 wrote:
         | It's not clear to me if the $920k is including his salary. If
         | he paid himself a good salary, the numbers will look different.
        
           | baxtr wrote:
           | It seems like the $920k include all profits. The sale alone
           | yielded $490k in profit.
        
             | mtlynch wrote:
             | Correct, I did not draw a salary.
        
         | nakovet wrote:
         | If you are maximizing income, go work for the company that pays
         | you the most. If you consider other things then it's not that
         | simple: * control on which project you work on * choose your
         | cooworkers * choose your office location * return to office
         | policies * choose process and bureaucracies It's about how many
         | degrees of freedom you want.
        
         | fuzzythinker wrote:
         | Money wise, FAANGs are more like 2x of $920k with comps. If the
         | output is guaranteed, and stress is kept at 2x FAANG, it's like
         | trading stress and the thrill and difference in experience for
         | money. I would choose this.
        
         | vdvsvwvwvwvwv wrote:
         | Meh. He could have made 10M or 0.
         | 
         | Google founders themselves could have got a nice job at IBM.
         | 
         | Op is free as in bird too.
        
         | fsckboy wrote:
         | > _so this gives an average yearly salary of 230k. Very close
         | to FAANG senior salary with much more risk_
         | 
         | this is just bad analysis, and as part of that you don't
         | understand risk.
         | 
         | Financial risk is _the variance of the expected outcomes_ , it
         | is not a component of the expected value. The risk that you
         | will fall short is always balanced by the risk that you will
         | strike it rich; otherwise, you have calculated your expected
         | value wrong. Expected value does not include variance, it's the
         | missing factor.
         | 
         | your faang salary is your upper bound on income, is the cost
         | you bear eliminating the risk; the risk the entrepreneur takes
         | is rewarded by the option on vast riches.
         | 
         | You are looking backward as if you could have guessed a priori
         | what would happen. If you could guess looking-backward-in-
         | advance that you'd wind up with a faang salary running your own
         | gig, definitely worth "the risk".
        
           | navane wrote:
           | I don't understand this. Afaik the parent argues that the
           | 230k/yr is a lucky outcome of starting a business, far more
           | people end up with less or nothing. And this "winning"
           | situation of gaining 230k/yr is barely in range of a "sure"
           | outcome of being employed at Google. Concluding that if even
           | a successful entrepreneur is set to gain less then an
           | employee at faang, entrepreneurship is not a sound decision
           | for fang employees. How is risk portrayed wrong here?
        
             | fsckboy wrote:
             | > _How is risk portrayed wrong here?_
             | 
             | because he portrayed risk as "the risk of losing money",
             | but that is not a proper definition of risk.
             | 
             | it's easier to understand the concept with the stock market
             | because there is a market price (there is not a market
             | price for startups). If a stock in the market has a price,
             | what does it mean to say that it's a risky stock? that it
             | might drop? No, not if you say that to the exclusion of the
             | risk that it might also go up.
             | 
             | If a company has a price in the market, and you are an
             | omniscient who can definitively say that there are a bunch
             | unaccounted for factors that increase the probability that
             | that stock will go down, what you would conclude (because
             | you are an omniscient who also understands risk) is that
             | the price of the stock is wrong, not that the riskiness has
             | been mis-assessed.
             | 
             | This is an important area of finance, it's the basis, or
             | rather the inescapable conclusion, of option pricing, the
             | famous Black-Scholes model. It turns out the option price
             | calculation does not contain any of the probabilities of
             | what might happen to the stock/company in the future, the
             | option price is only based on the _variance_ of the
             | outcomes. How can that be? Turns out the probabilities (the
             | expected value) have already been accounted for in the
             | market price of the underlying security. If a market is
             | fairly pricing stocks, riskyness means degree of variation
             | in outcomes.
             | 
             | There is a probability in variance, the probability "that
             | you will wind up away from the mean". the FAANG salary is
             | the mean, with no risk, meaning you aren't going to fall
             | below or go above. He called out the other option as
             | "risky" and somehow decided that the outcome this founder
             | experienced was the upper limit, had no chance of being
             | higher. He had no basis to think that, and his analysis is
             | basically Monday night quarterbacking. "Since you didn't
             | make the field goal, you shouldn't have tried, should have
             | tried for a touchdown instead", ignoring that on average
             | it's easier to get a field goal.
        
       | dbacar wrote:
       | Thanks for sharing with such clear concise information. I believe
       | this is very valuable insight for some of us.
        
       | mtlynch wrote:
       | Author here.
       | 
       | Happy to answer take any feedback and answer any questions about
       | this post.
        
         | simultsop wrote:
         | how many businesses you run?
        
           | mtlynch wrote:
           | Right now, I just have one business that makes money. It's an
           | ingredient parsing API that I wrote in 2018.[0] It was not a
           | good idea, but it still makes $100-200/mo without me doing
           | anything. Until a few months ago, I also had a website about
           | the keto diet that made about $100/mo, but I sold it because
           | I wasn't doing anything with it.[1]
           | 
           | I'm currently working on a book about writing as a developer,
           | and that's my main focus for the next few months,, but I
           | don't know if I' call it a business because I haven't sold
           | anything yet.[2]
           | 
           | [0] https://zestfuldata.com/
           | 
           | [1] https://mtlynch.io/notes/buy-is-it-keto/
           | 
           | [2] https://refactoringenglish.com
        
             | akomtu wrote:
             | Imo, you can make good money, and do some good, guiding the
             | numerous laid off developers on the business pastures, if
             | only you figure out how to scale beyond the usual personal
             | couch model. Perhaps some sort of QA platform with paid
             | access: free-tier for read-only users, basic-tier allows
             | asking questions, and premium users get occasional 1-1
             | guidance? Just a random idea. This might work because they
             | can relate to you and thus trust you, unlike yet another
             | MBA suit.
        
             | hellohelu wrote:
             | Thanks for the article. Great read. Can I ask how you sold
             | the website making $100 month?
        
         | fragmede wrote:
         | Given the numbers, the stress, the freedom, the self-
         | actualization, would you still quit Google and take this
         | journey, knowing then what you know now? Do you feel richer or
         | poorer for the experience? What's next for you?
        
           | mtlynch wrote:
           | Re-posting from a similar answer I gave in another thread:
           | 
           | Yep, still happy with the decision. A lot of my comp at
           | Google was stock, so I would have made a lot from the stock
           | price movement over the last six years, and I'm a bit envious
           | of that, but still yes.
           | 
           | I do still love the independence of working for myself, so
           | I'm happy to have had the last six years of that rather than
           | feeling unfulfilled at Google.
           | 
           | With everything shifting around AI, and big tech could be
           | doing massive dev layoffs in the next five years. Given that
           | risk, I'm happy to have experience as a founder rather than a
           | dev who could be laid off immediately in a down market.
           | 
           | https://news.ycombinator.com/item?id=42126800
           | 
           | > _Do you feel richer or poorer for the experience?_
           | 
           | Definitely richer. I'm glad I did it, and it was so much more
           | meaningful than the work I did at Google or any previous job.
           | 
           | > _What 's next for you?_
           | 
           | My wife and I just had our first child over the summer, so
           | I'm mostly on paternity leave to enjoy time with my family,
           | but I'm slowly easing back into work. My next project is a
           | book about what I've learned about writing effectively as a
           | software developer.[0] Eventually, I'd like to try building a
           | SaaS, but working on a book is much friendlier to an
           | unpredictable work schedule at the moment.
           | 
           | [0] https://refactoringenglish.com/
        
             | fragmede wrote:
             | Congratulations on the kid!
        
               | mtlynch wrote:
               | Thanks! It's been really fun. Of course, challenging at
               | times, but overall I'm really glad I've had this time off
               | to enjoy with my family.
        
             | MattSayar wrote:
             | Have you had any consulting or speaking opportunities come
             | up from these blog posts?
        
               | mtlynch wrote:
               | No, nobody's ever really reached out about
               | consulting/speaking. I haven't pursued it either, as I
               | prefer to have products rather than making money from
               | one-off jobs.
        
         | optymizer wrote:
         | Thanks for the article and for including so many specific
         | numbers in it for our benefit (details that I imagine many
         | others might have decided to omit).
         | 
         | Now that you've been through this process, how would you go
         | about finding a buyer yourself?
         | 
         | Also, are there any resources you found valuable for starting
         | your business? How did you go about hiring your first employee
         | and setting everything up for them as employees?
         | 
         | Again, thanks for the writeup and congrats on the sale!
        
           | mtlynch wrote:
           | Thanks for reading!
           | 
           | > _Now that you 've been through this process, how would you
           | go about finding a buyer yourself?_
           | 
           | It would have been tough to find a buyer. Before I met Quiet
           | Light, I was worried a broker wouldn't take me, and I'd have
           | to find a buyer myself. So my plan was to (in order) start
           | more loudly telling other founders that I'm looking for a
           | buyer, reach out to more adjacent companies pitching them on
           | a strategic acquisition, discuss on my blog that I'm looking
           | for a buyer, and if all else fails, put up a banner on the
           | store website saying the company is for sale. The problem was
           | that the more loudly I advertise the company is for sale, the
           | more obvious it is to buyers that I'm desperate to sell. It
           | also risks spooking customers who might not want to buy
           | hardware from a company whose ownership is about to change.
           | 
           | > _Also, are there any resources you found valuable for
           | starting your business?_
           | 
           | Minute for minute, the best resource I've found is Jason
           | Cohen's talk, "Designing the Ideal Bootstrapped Business."[0,
           | 1] The key insight for me is that bootstrapped businesses
           | have very different strengths and weaknesses than a VC-backed
           | startup, so you should pick a business that plays to those
           | strengths.
           | 
           | I also enjoyed _Start Small, Stay Small_ by Rob Walling [2]
           | and _The Mom Test_ by Rob Fitzpatrick[3]. The tl; dr from
           | those is that you need to avoid the trap of building
           | something for months and then looking around for customers
           | once it 's done. You instead should flip it and talk to
           | customers before you even start and find out what they need.
           | 
           | It's not a book or resource, but one of the most valuable
           | things I did and wish I did it earlier was create a course.
           | It's a very condensed version of the experience of
           | bootstrapping a business because you need to identify a need,
           | create a product that fills the need, then market it to
           | customers. And you don't have to be the world expert on
           | anything, you just need to know enough to get someone who's
           | at level N to level N + 1 and who likes the way you explain
           | things. And you can pick a small topic and create a course
           | with 30-100 hours of work.
           | 
           | I spent 60 hours on my first course, and it made $10k, so
           | it's not like a smash hit, but it's the highest ROI thing
           | financially I've done since quitting Google.
           | 
           | > _How did you go about hiring your first employee and
           | setting everything up for them as employees?_
           | 
           | In the first few months, I was assembling all the devices,
           | packing boxes, and printing out instruction sheets myself. It
           | wasn't sustainable because I was also trying to write code
           | and do customer support. It was during COVID and my wife and
           | I were quarantining strictly, but she also was looking for a
           | job since she was in grad school, so she was employee #1.
           | 
           | We started with just Google Docs. I'd write things and share
           | them with her, and she'd ask questions or make updates.
           | 
           | My next hires were developers, which was a pretty dumb
           | decision because it's the most expensive role, and it's the
           | job I like doing most myself. I was finding that I didn't
           | have time to advance the product because customer support was
           | taking too much time, so I should have hired a customer
           | support person. But I hired devs because I'd hired devs
           | before and worked with a lot of devs, so it was a role I felt
           | comfortable hiring. For that, I tried to add lots of
           | automated checks on Github and document things there. I also
           | wrote guidelines on my blog that became official guidelines
           | for devs within the company.[4]
           | 
           | We moved into an office in early 2021, and at that point, I
           | had to hire real W-2 employees rather than contractors. For
           | that I used JustWorks, which I hated. I switched to Gusto,
           | and they were poor but not terrible. In the future, I'm going
           | to avoid creating a business that needs W-2 employees because
           | in the US, it's just set up so badly for small businesses to
           | manage the paperwork around it.
           | 
           | As we were moving into the office, we also switched from
           | Google Docs to Notion, and I had a good experience with
           | Notion. It's set up well for internal documentation, and it's
           | user friendly, so it's easy for everyone to do basic
           | searching and editing.
           | 
           | I could go on and on about hiring, but those are the biggest
           | things that come to mind.
           | 
           | [0] https://www.youtube.com/watch?v=otbnC2zE2rw
           | 
           | [1] https://mtlynch.io/notes/designing-the-ideal-
           | bootstrapped-bu...
           | 
           | [2] https://mtlynch.io/book-reports/start-small-stay-small/
           | 
           | [3] https://mtlynch.io/book-reports/the-mom-test/
           | 
           | [4] https://mtlynch.io/freelancer-guidelines/
        
         | alberth wrote:
         | (been an avid reader of your posts over the years. thanks so
         | much for sharing!)
         | 
         | Q: personal guarantee loans/contracts
         | 
         | I know it's common practice for lenders & commercial real
         | estate to make small business owners personally guarantee the
         | loan/contract.
         | 
         | Did you have any of this? And if so, how did you unwind those
         | contract?
        
           | mtlynch wrote:
           | Thanks for reading!
           | 
           | No, the only place where I was personally on the hook was
           | credit cards, but that was fine because I just paid the
           | balance and closed the accounts.
           | 
           | I maybe had to give a personal guarantee to rent our office,
           | but it was $600/mo and the landlord was extremely laid back
           | and agreed to month-to-month after our lease was up.
           | 
           | I didn't take out any small business loans to start the
           | business, as I started it with my own cash, and then it
           | generated enough revenue to sustain itself.
           | 
           | The buyer may have had more complicated agreements with his
           | lenders to purchase the business, but I wouldn't be exposed
           | to any of that.
        
         | gwbas1c wrote:
         | Just wanted you to know that I've been looking at a lot of your
         | blog entries for Tiny Pilot over the last few years. This is
         | the first one I've skimmed to the end.
         | 
         | Great writeup!
        
         | depr wrote:
         | >I didn't want a bad outcome for anyone, but the worst case for
         | me was significantly worse than the worst case for any other
         | member of the team.
         | 
         | Your worst case is you lose the deal and the time and money you
         | spent on it, and their worst case is they are fired and lose
         | their healthcare (that is how it works in America right?), is
         | that correct?
        
           | mtlynch wrote:
           | Thanks for reading!
           | 
           | > _Your worst case is you lose the deal and the time and
           | money you spent on it, and their worst case is they are fired
           | and lose their healthcare (that is how it works in America
           | right?), is that correct?_
           | 
           | Yeah, I get that perspective.
           | 
           | As I said, I don't think there's any good solution here. I
           | don't think it's fair for me to hand the company over to
           | someone who might just fire the employees, but I also can't
           | promise to keep everyone in their role forever regardless of
           | a sale.
           | 
           | For added context, everyone at the company worked part-time,
           | generally a max of 20 hours per week. Some were contractors
           | who had multiple clients, others were founders with their own
           | side projects, and others worked part time because they
           | wanted to focus on other things in their personal life.
           | Nobody had healthcare insurance through the company.
           | 
           | So, in the worst case of an owner coming in and firing
           | everyone, it would suck, but it's also not like anyone would
           | be like, "Oh no! I just bought a new house on the expectation
           | that I'd be at the company for the next 20 years!"
           | 
           | The worst case for me isn't just that I lose some time and
           | money. I was terrified of not being able to sell the company
           | by the time my son was born. I was the sole founder and
           | manager, so I can't exactly say, "Okay, I'm going to take a
           | few months of paternity leave. Pay yourselves and our vendors
           | while I'm gone." So I'd be probably in a position of letting
           | down both the team and my family trying to keep the company
           | afloat while becoming a new father.
        
             | depr wrote:
             | Alright, thanks for answering my question!
        
         | LouisSayers wrote:
         | One thing that wasn't really covered was: why did you sell?
         | 
         | Especially at a 2.4 multiple... It seems like you could have
         | just let it keep running mostly on autopilot (assuming the team
         | could keep working on improvements)?
        
           | mtlynch wrote:
           | Thanks for reading!
           | 
           | I wrote about that in a previous post:
           | https://mtlynch.io/i-sold-tinypilot/#why-sell
        
         | astonvilla wrote:
         | Great writeup. The writing was clear and engaging that it made
         | me want to read it, even though I'm not in the industry. I have
         | a question that is adjacent to your experience, but not
         | specifically about the post. But hopefully your experience of
         | founding a company for four years could shed some insight. Some
         | background: I'm an incoming medical school student, and
         | sometimes I wish I went into tech rather than medicine. My
         | question: would it be worthwhile for a medical student to
         | invest time to learn programming in order to potentially found
         | a software company (I know you founded a hardware company, but
         | previously worked as a software engineer)?
         | 
         | Now I know this is such a broad question, with many factors
         | that could influence whether this pursuit is worthwhile, but
         | maybe your experience could point out whether this is even
         | something to consider. For example, would I even gain the
         | necessary skillsets required to found a company whilst pursuing
         | medicine? Would knowledge of tech compliment a medical-related
         | company, or would I better spend my time working on the non-
         | tech side of a company?
         | 
         | Your writing is great to highlight the complexities in the
         | world of indie businesses. Thanks.
        
           | mtlynch wrote:
           | Thanks for reading and for the kind words!
           | 
           | First, a meta comment is that I've found that you should
           | weigh advice based on how similar the advisor is and how
           | closely their success matches what you want. So, given that I
           | came in with a background in software already, my advice
           | might not be a good match for you.
           | 
           | I feel like I went down a lot of misguided paths as a founder
           | following advice of people who were successful but were very
           | different from me (e.g., their goal was to reach $1B in
           | valuation, they love pitching to customers).
           | 
           | That said, the thing I recommend to a lot of people curious
           | about starting out with an indie business is to create a
           | course or a book. People call these "info products" and that
           | term has kind of a stench to it, but I think they're a great
           | way to learn. I prefer the term "educational product" because
           | there's less of a stigma. I created a video course in year
           | three of going off on my own, but I wish I'd done it sooner.
           | 
           | I think people feel reluctant to create an educational
           | product because they feel like they're not an expert at
           | anything, but you don't have to be the world expert on
           | something to make a course. You just have to know enough that
           | you can get your students from level N to level N + 1. You
           | can take something that you recently learned and make a
           | course that you wish that you'd had that would have let you
           | learn the same information in 5 hours rather than 50 hours.
           | And you don't have to be the world's greatest teacher as long
           | as you can find some people who enjoy the way you explain
           | things.
           | 
           | Creating an educational product is like a microcosm of the
           | full experience of launching a business. It forces you to
           | think about what customers want, build something that fills
           | the need, and then market it to find customers who want it.
           | And all that stuff is hard, but it's much easier to do with a
           | course. If you spent 50 hours making a course and find out
           | you can't sell it, you lost 50 hours. You can learn from the
           | failure and try a new course or product the next month. If
           | you spent 2 years learning to code and building a tech
           | product and find that nobody wants it, you'll feel very tied
           | to that idea and have a hard time pivoting to another idea.
           | 
           | I have my issues with Pieter Levels, but I think he's a great
           | case study in trying businesses rapidly and then doubling
           | down on the ones that work. When he started, he didn't know
           | how to code well, so his early products would just be like a
           | Google Sheets spreadsheet that he sold access to.
        
         | negus wrote:
         | Thank you for the hint about the business phone registered in a
         | call redirect service.
        
       | hartator wrote:
       | 2.4x annual profit seems like a pretty bad deal.
        
         | toasterlovin wrote:
         | Low multiples are pretty normal for a small business. There's a
         | lot of risk for the buyer. IMO it makes selling an ongoing
         | concern not worth it if you can significantly reduce the time
         | required to just keep running the business.
        
       | ekanes wrote:
       | These are very insightful, thank you for sharing this @mtlynch
        
       | antoniuschan99 wrote:
       | Congrats on the sale! Wondering what your thoughts are of these
       | extremely low cost kvm's from Sipeed (NanoKVM)?
       | 
       | Do you think that allows you to expand your market since the
       | hardware is cheaper as you maintain great user experience? Or
       | does that force you to go upmarket as hobbyists need only the
       | minimal feature set?
       | 
       | A lot of very cheap risc-v boards like milk-v duo sbc are
       | available now
        
         | mtlynch wrote:
         | Thanks!
         | 
         | > _Wondering what your thoughts are of these extremely low cost
         | kvm's from Sipeed (NanoKVM)?_
         | 
         | > _Do you think that allows you to expand your market since the
         | hardware is cheaper as you maintain great user experience? Or
         | does that force you to go upmarket as hobbyists need only the
         | minimal feature set?_
         | 
         | To be clear, I'm totally gone from the company at this point,
         | so I'm not thinking about strategy for TinyPilot at all
         | anymore.
         | 
         | But I will say that every year, I'd see a new KVM over IP pop
         | up that claimed that they were going to undercut TinyPilot by
         | 60%. And then they fizzle out, and I never hear from them
         | again.
         | 
         | My suspicion is that people see TinyPilot and say, "Wow, that
         | looks like $100 worth of hardware being sold for $400!I could
         | do what they're doing and sell for $200 and eat their lunch and
         | still make $100 on every unit!" But then as you get into it,
         | there are all these more subtle costs like compliance testing,
         | tariffs, customer returns, insurance, etc.
         | 
         | And that's before you even get to customer support. For a KVM
         | over IP, you can't just give customers a "have you tried
         | turning it off and on again?" support response because the
         | issues are more technical and deal with things like NATs and
         | proxies. So if you're making $20 per sale on a low-cost device,
         | and then the customer has one conversation with a support
         | engineer, you lost your profit and probably would have been
         | better off not selling to them at all.
         | 
         | So, I think there's room to reduce prices as hardware prices
         | come down, but I'll be surprised if other vendors can slash
         | prices to below $100 and still run profitably in the long-term.
        
           | restalis wrote:
           | Can't those "more subtle costs" be pulled out of the product
           | cost itself and offered or at least expressed separately? Say
           | customer support, if it'd be offered as a paid service
           | instead of "free" as in baked-in-product-cost, thus giving
           | the customer a choice to either go for that easy-pick fruit
           | of available paid support, or the alternative of investing
           | more of their own effort into figuring out and solving the
           | encountered problems by using the docs available to them, or
           | maybe giving up on the problematic use-cases in the first
           | place? Or tariffs - is it bad to let the customers know that
           | there are cost differences in the product offered to them due
           | to their request coming from different tariff-impacted
           | markets?
        
       | aimazon wrote:
       | "My lawyer warned me that when I sell my business, I lose limited
       | liability protection. If the purchase agreement didn't limit my
       | liability to the buyer, the buyer could later sue me for any
       | amount, even if it exceeds what they paid in the acquisition."
       | 
       | "Sales below $1M are usually asset sales, meaning that the buyer
       | is purchasing assets from the business but not the business
       | itself. So, I technically still own a company called TinyPilot,
       | but I transferred all of its physical and intellectual property
       | to the new owner."
       | 
       | Aren't these contradictory? If it's an asset sale, the deal is
       | between TinyPilot LLC and the buyer for the assets.
        
         | mtlynch wrote:
         | Author here.
         | 
         | Yeah, that seemed strange to me, too, but that was how my
         | lawyer told me it worked. And the buyer's lawyer cared enough
         | to fight about the exact amount of liability, so I assumed the
         | buyer's lawyer felt that way as well.
         | 
         | In practice, it seems like liability protection would have to
         | change in some way otherwise the seller could abuse the system.
         | Like imagine that I sell the new owner $200k worth of inventory
         | and then the new owner discovers that, unbeknownst to either of
         | us, the inventory has some kind of defect and is unsellable. If
         | the buyer comes back and says, "Hey, I want my $200k back," it
         | would be strange if I'm allowed to say, "Oh, too bad for you.
         | I've shut down the LLC that sold you that inventory and moved
         | all the money to my personal accounts, so there's no money for
         | you now."
        
           | aimazon wrote:
           | A typical acquisition of the legal entity from the
           | shareholders provides protection because there's no limited
           | liability in the deal (as it's a sale by the shareholders (as
           | individuals)). An asset sale has higher risk for the buyer
           | (because the sale is, essentially, looting the corpse of a
           | legal entity) with the benefit of not having any liability
           | for the legal entity's past deeds. Purchasing assets from the
           | company while also expecting the former owner to be on the
           | hook for the value of assets is trying to eat their cake and
           | keep you on the hook to make them another cake.
           | 
           | That said, U.S. LLCs are not normal limited liability
           | companies (like they are in the rest of the world). A U.S.
           | LLC is a weird amalgamation of tax and law. Perhaps what
           | you're describing (as described to you buy your lawyer) is
           | just one more weird aspect of U.S. LLCs.
           | 
           | (Outside of the U.S., a limited liability company is nothing
           | like a U.S. LLC. The closest the U.S. has to a typical
           | limited liability company is an Inc.)
        
             | mtlynch wrote:
             | Thanks! That's helpful context.
        
         | amccollum wrote:
         | I don't know about the author's case, but often asset purchase
         | agreements will make the principals / shareholders party to the
         | agreement personally with specific liability provisions. If
         | there are no assets left in the company, the buyer has no
         | recourse against it, since it is essentially an empty shell (in
         | certain cases, insurance could be an exception to this). As a
         | buyer, you will want to have some protection against issues you
         | don't know about at the time of sale (perhaps because you
         | weren't told about them, or the seller was negligent).
        
       | neilv wrote:
       | > _If I do this again, I'd wait to tell my team about the sale
       | until it's a done deal, but I'd also make sure the team knows
       | that an acquisition is always a possibility. I'd explain before I
       | even start looking for a buyer that an acquisition might happen,
       | and that the team won't necessarily know it's happening. If it
       | did, I'd prioritize a buyer whose vision aligns with the team's
       | interests, as I did with TinyPilot._
       | 
       | > _This strategy is not ideal or fair to everyone, but it feels
       | like the least bad of many flawed options._
       | 
       | That's better than the norm, but I agree it's not entirely
       | satisfying.
       | 
       | For sales larger than the one the author wrote about, I wonder
       | whether the possible problems that the author mentioned could be
       | averted by making the sale a win for the employees.
       | 
       | Ideally, the employees already would have enough vested equity,
       | for the sale to be positively life-changing. But if not, maybe,
       | as the sale is planned, everyone gets issued RSUs that vest
       | immediately if and when a deal closes? Or bonuses? Or maybe the
       | sale terms include retaining everyone for at least a year at
       | double compensation?
       | 
       | (More generally, I believe in cutting in early startup employees
       | on equity in a more significant way than is conventional. And
       | maybe the imminent-sale alignment risks are another instance in
       | which significant pieces of the pie would help and be
       | appropriate.)
        
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