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My eighth year as a bootstrapped founder

mtlynch.io

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Re: My eighth year as a bootstrapped founder

#91

Post by skeeter2020 »

mtlynch wrote: post #25
mrdependable wrote: post #21

I've had a similar journey to yours. Started January 1st 2019, early 30s, had a second kid. Loving every minute of it, though I do wonder when the fun is going to end. Every year I'm surprised the business keeps growing. This year my goal is to diversify to try and ease that gnawing anxiety, but every time I try working on something else I feel guilty about ignoring what's already been working for me. Tempted to just…

I recommend having an initial talk with a broker if you're thinking about it at all. The brokers I've met are happy to talk if you have a profitable business, even if you don't plan on selling anytime soon, and you don't have to sign anything to commit to them. They can talk to you about what you can do to prepare for an exit even if you don't expect that to happen for several years (and it might take you several yea…

This is a really good idea, similar to raising money when you don't need it. It could help prevent you from making a mistake or getting into a unattractive position for when you are thinking of selling. I've seen this with one & few person companies, everything from messy ownership & cap tables, to tax obligations, to the structure of multi-year sales or contracts. This is why even big PE portfolio companies start planning for a sale years in advance; the difference (making it harder for you IMO) is that they have a pretty good idea when the sale will happen.

Re: My eighth year as a bootstrapped founder

#92

Post by skeeter2020 »

simgt wrote: post #75
hdjrudni wrote: post #69

Earlier quoted context omitted.

I just sold my first solo(ish) business, so I can speak to this a bit. 'ish' because I had a partner, but he was non-technical. AI is a boon. I'm currently finding it works best in apps that have established patterns but aren't enormous. If you lay some groundwork (as I did, because the AI didn't exist when I started), it's quite lovely for migrating heaps of old code and just doing all those annoying little things w…

As a technical person, how does one find a non-technical business partner? ;) I know about Entrepreneur First, but that's not for bootstrapping and has a too much of the unicorn vibe for me. The obvious is of course luck through one's social network.

>> The obvious is of course luck through one's social network.

I'd really counsel you to pursue this but not focus on the luck piece of it (which really is a big part). Just like hiring works best when it's a recommendation of a known good hire, look to your 2nd (and possibly 3rd) degree network. Force yourself to attend events, programs and communities (irl & virtual) outside of your direct sphere of expertise. Economic development orgs in your city/region might work too. Maybe you can do it with some help/practice and don't need a partner? You could be looking for a support network more than business expertise; the good news is IME that's easier to find than a partner.

Re: My eighth year as a bootstrapped founder

#94

Post by isjsiwndkwj »

jwr wrote: post #76
switz wrote: post #12

Thanks for being so transparent. As a fellow solo bootstrapper, I think the thing people most often misunderstand is the relative inconsistency (income, "wins", the camaraderie, etc.) so it's nice for you to bare all. That being said, you do get the consistency of independence and autonomy. As I watch my peers deal with crappy work environments, losing their jobs, and other bullshit, I just keep chugging along: self-…

> I've found it tough to talk about being a solo bootstrapper though. People don't seem all that interested in it [...] I think you've hit the nail on the head (solo bootstrapper here): People are not interested because A) it's not about them, it's about you, B) it sounds somewhat scary, C) it sounds completely detached from their reality of corporate jobs, and finally D) it's scary because your life might be "better…

[dead]

Re: My eighth year as a bootstrapped founder

#95

Post by skeeter2020 »

mtlynch wrote: post #41
leros wrote: post #36

Looking back, how do you feel about your slate of past projects? I'm curious as TinyPilot is your most successful project and it looks like the most business-oriented thing you built: as in, its a product aimed at serious businesses. Whereas Zestful is a niche micro-saas and Is It Keto is a niche website. Perhaps I'm characterizing things wrong, but that's my rough perception.

Thanks for reading! > Looking back, how do you feel about your slate of past projects? I feel like I learned something valuable from all of them. The ones I'm most proud of are TinyPilot, my book, and my blogging course (in that order). Those are, uncoincidentally, the ones where I found product-market fit, whereas the rest never really achieved that. TinyPilot was business-oriented by mistake. When I initially made…

>> I found that my customers were much more interested in paying a higher price for a pre-made device than saving money with a DIY solution

This could have been a 50-yr-old comment about the Apple I computer! Lol

>> Wozniak intended to share schematics of the machine for free; however, Jobs advised him to start a business together and sell bare printed circuit boards (PCBs) for the computer, without any components soldered on.

...

Terrell told Jobs that he would order 50 units of the Apple I and pay $500 each on delivery, but only if they came fully assembled – he was not interested in buying bare printed circuit boards with no components.

https://en.wikipedia.org/wiki/Apple_I

Re: My eighth year as a bootstrapped founder

#96

Post by isjsiwndkwj »

jwpapi wrote: post #50
switz wrote: post #12

Thanks for being so transparent. As a fellow solo bootstrapper, I think the thing people most often misunderstand is the relative inconsistency (income, "wins", the camaraderie, etc.) so it's nice for you to bare all. That being said, you do get the consistency of independence and autonomy. As I watch my peers deal with crappy work environments, losing their jobs, and other bullshit, I just keep chugging along: self-…

I get exactly what you are saying, but honestly man freedom is the best. I’m so happy every day as long as I have my computer an can work on taking over the world. Every day feels like school holidays to me

[dead]

Re: My eighth year as a bootstrapped founder

#97

Post by isjsiwndkwj »

Is a massively inflated ego a requirement for bootstrapping?

The conversation here is centred on how others simply “do not understand how awesome I am for bootstrapping”. All veiled under a very transparent layer of self-aggrandising faux-humility.

What is the deal with that? Compensating for something?

Re: My eighth year as a bootstrapped founder

#99

Post by paulddraper »

skeeter2020 wrote: post #90
paulddraper wrote: post #52

Earlier quoted context omitted.

Assuming it’s an S-corp, Founders will try to get as much as possible in profit/dividends, as that is taxed better than income.

when your annual revenue is < $25K this is not typically a concern. Also that's true from the corporation's perspective but not always true because of the double taxation from the individual's side. I always find the timing flexibility (which effective tax year) far more valuable than the employment vs. investment income differentiation.

Dividends aren’t double taxed?

Unless I’m misunderstanding something.

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