Why I switched sides: From bootstrapping to VC (opens in new tab)

If your bootstrapping is failing financially, or not meeting your own needs (as described in the article), VCs are a valid choice to kick it back up to try to succeed. Better that than shutting down. But the anti-VC perspective is talking about a different scenario: If your bootstrap is working, they would argue not to take on VC just to speed it up or meet some cultural expectation of a funding milestone.

Which ultimately sums up the article for me - their particular bootstrapping wasn't working for them, so they switched to the VC route.

Agree taking funding brings back an element of having a boss again Alan. It's certainly a trade-off of the VC route, and one of the main reasons I haven't taken funding before.

That said, I still think you get a good amount of autonomy by (co-)founding a startup, as you're often free to execute how you choose, but with the agreement that you'll pursue a path that can give an outsized return for your investors. Investors rarely want to dictate what and how you do things, in my experience.

> When does that ever stop being true?

Again I agree it doesn't, but it's something many bootstrappers don't quite understand when starting out (I didn't way back when), and I think is a point worth noting.

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Happy to make edits if there's ways I can clarify this better. Gotta ship something before EOP today but will revisit the article tonight.

[0] https://www.goodreads.com/book/show/35957156-lost-and-founde... [1] https://tinyseedfund.com

More on the messy parts: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/...

That said, you shouldn't take money unless you think there's a good shot at success. I've done a VC startup and the overall hassle, stress, and lost time made me want to take a job (a good one) in preference to most things that don't seem like sure bets at the start. My company failed because we never articulated a vision bold enough to raise serious VC. I'd probably be richer if I'd taken more risk but I'm not at all sure I'd be happier.

So.. there is certainly a key element of control and motivation in a bootstrapped business vs a business with outside investors. But AFAICT, nothing fundamental about level of difficulty or quality of life.

> One thing that is undeniable is that a bootstrap will always leave you in control at the end of the day.

I agree bootstrapping gives you more say over which way you take the business, and hopefully that came across in my post (although I only mentioned it briefly).

> I think a product should not be made for the potential profit it could amass but to fill a need for these users, listening to them feels like the next logical step to take (and most companies, even tremendously giant ones, still fail to do this I feel like).

I agree we should be motivated by more than money. As I mention in the post, money is a bad master but a great servant. We need money to serve us, so we can feed our families and keep the lights on, but money itself shouldn't be the goal. I realise when taking funding this confuses the matter, as now you're not just responsible for your family, but for providing a return to your investors. I still believe it's possible to be mission-driven having taken funding, but understand it can complicate the matter.

> Even more important than that is that it might not be the next unicorn, but that is absolutely fine for some people. They just want enough to feed themselves and their families while having a sane work life/rhythm of say 4-5 hours a day once you get it rolling.

I agree the end goal for us is often spending time with those we love, whilst having that sense of purpose I mentioned in the post. We all want to leave some impact on the world, maybe that's a partner or children who know we loved them, maybe it's a few hundred paying customers who love your product, maybe it's some big swing towards a big dent in the world.

My co-founder and I are relatively counter-cultural in the startup world, admittedly it's early days, but we don't work crazy hours as our belief is that the long hours are often busy work, not important work. If we can look after ourselves, not get burnt out, make wise decisions from a place of rest and do important deep work regularly, we believe we can outcompete any startup bro culture that works 80+ hour weeks.

> I feel like the author used to somewhat adhere to this moto but somewhere along the way got lost and is now simply after the money for the sake of it.

I don't believe that's the case, personally. My current wage is half that of 2 other contracting roles I was offered at the same time as this gig. I'm fully aware the vast majority of startups fail, so I'll very likely be out of pocket. I took the role as I admire my co-founder and wanted to learn from his product skills, an area I realised I needed to grow in.

Before taking this role I used to work a full-time job, come home in the evenings and work on my side-hustle. For 3 years it meant I didn't really have a life outside of the day job and the side hustle. Now I normally work 8-4, home by 5 and have the evening to meet friends or relax. People often think taking funding means having less work/life balance, right now for me it's the opposite (again, caveat we're early days).

I agree bootstrapping itself wasn't the problem. The problem was that I felt my focus on building a business on the side of my day job limiting to what I could do next. At the start of the year I decided the healthiest thing for me to do was to start from a clean slate and bed down somewhere. I wasn't sure where, but London is where I ended up.

I realise there are much more sane ways to live our lives than a startup, bootstrapped or funded. I agree it takes a lot of personal sacrifice too, mentally more than anything.

I realise my path looks strange, going from "I need more time to focus on things outside of work" to "I'm starting a startup", and it was never my plan when I came back. It was only 4 months after returning that the opportunity came up and it was the best fit for me at the time.

I may be too naive, but both myself and my co-founder believe that working excessive hours isn't a necessity to make a startup succeed. Sure there are times when you need to work longer in short periods to get something over the line, but the idea that being on the brink of burnout gives the best odds of success goes against what I've read about how the human mind works, and my experience too.

Maybe in a year or two I'll do a follow up post.

A point of clarification that didn’t make the article: we’ve not technically raised VC funding yet, we’re in an incubator. But we’ve effectively raised an initial round via our budget, and are on the path to raise our first round proper.

I agree with the rough sentiment of what you’re saying but think it’s a slightly too narrow point of view. Joining an incubator or accelerator helps minimise downside whilst in the process of figuring out the problem space and whether your hypothesis have legs. Sure, you can do this as a side hustle first and that’s great too, but as I say in the article, it depends on your circumstances.

I’m not raising money specifically because of personal life challenges, deciding to raise only came after making the big life adjustments. It’s my belief that raising can sometimes be less pressurised than bootstrapping, though admittedly most startup founders don’t live it out that way. We’ve got our beliefs based on what we know and our experience so far, I look forward to walking it all out and reporting back on what I learn.