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What 6 years of bootstrapping a startup has taught me

37 points by helpstay 7y ago

jagged-chisel 7y ago
> In essence, bootstrapping your startup is the new cool thing. I feel like this minimizes an important truth: that taking investment tends to mean losing control. Founders see that and want to maintain control.
- mLuby 7y ago
  That's why it's cool; coolness is value, independence, and self-control (lit. "keeping your cool").
  - jagged-chisel 7y ago
    Sure, I get that. And it is cool. I just felt like the statement was a bit too reductionist. Enough so to make the comment.
ganeshkrishnan 7y ago
I feel like an in-between/better option than bootstrapping or VC investment is going for an accelerator or incubator. You get the all important human connections, a bit of elbow room for money and a nice way to interact with other fellow founders. It still is a bit of stretch to get into an accelerator especially if you are before product market fit or if the product is in an very "unsexy" space (like supply chain).
- peterbell_nyc 7y ago
  I've usually seen most accelerators as an onramp to a venture backed business. I've raised for a couple of startups and with one I went through an incubator and it was great. Right now, I work from home, have a 3 year old and just went all in on a very modest little lifestyle business. I can't imagine an accelerator being much help, and given my goals for the business, I'd be a waste of a slot in their cohort.
  - algo_trader 7y ago
    Can u maybe share how much traction you had pre-accelerator and how much traction u had before a bigger seed/SeriesA ? My perception is at an accelerator or a $100K angel is really basically a nice pitch + MVP + some token revenue or customer maybes. I get it that if u are building yet-another-analytic-service, then the bar is higher.
- algo_trader 7y ago
  > bit of stretch ... accelerator.. before product market fit I dont get this. AFAIK accelerator is like ~$50K-$150K. What kind of product fit can u possibly reach before your first $50K ? Even a fully functional MVP only really shows basic execution ability. No?
carlisle_ 7y ago
This blog post seems more like a marketing grab with generic platitudes than it does genuinely helpful advice.
- tnolet 7y ago
  yes, it's copy & paste content littered with ads...
- dplgk 7y ago
  Like "For the first time in 40 years, the tide is starting to change". Says who?
goatherders 7y ago
"Build a business where you can do most tasks yourself" That is literally NOT a business.
- zemvpferreira 7y ago
  Underrated comment. I have nothing against bootstrapping but a business that you can’t easily sell or get away from, where you have no leverage on or ability to fully delegate is closer to being a job than it is a business.
  - goatherders 7y ago
    Somehow my original comment got downvoted, which is bizarre. I can only guess it offended someone that thinks "creating work = creating a business." There is NOTHING wrong with creating work for yourself if you get paid for it. Half of my time is spent consulting and that is not a sellable or delegateable "business." It's me selling my time. Lots of people do that and it is fine. But starting a venture where you keep your arms around all of the critical tasks is not building a business. A business is a set of systems and processes that can be performed, managed, and recorded without reliance on a single individual.
gramakri 7y ago
Small typo. "Business is a discipline, you’re in it for the long hall". It should be "long haul".
- danvoell 7y ago
  No, I think he means he is in it so that he can buy a house with a long hallway. :)
  - whycome 7y ago
    'Long hall' just gives me visions of death metaphors and "light at the end of a tunnel"
- helpstay 7y ago
  Thanks for pointing out the typo, fixed now :)
jiveturkey 7y ago
worthless article ... if you believe the title. this has almost nothing to do with bootstrapping per se. i don't know if the author is confused about it or just trying to draw clicks. decidedly untrue statements like 'For the first time in 40 years, the tide is starting to change' and 'when starting an enterprise' don't help. the fact that the specific business being discussed is almost certainly not one that could attract VC money anyway also doesn't help the author. a title that would make this article more reasonable is 'from side hustle to a viable one-man business in 6 years'. well, it's not specifically about side hustles either but it is reasonable albeit generic advice for one-man shops (possibly with some replaceable helper employees), for niche services such as skylight installer, gutter installer, ikea assembler, or as in this case, a subscription based marketplace for very tiny yet viable markets that can't be serviced adequately by large platforms.

37 points by helpstay 7y ago

> In essence, bootstrapping your startup is the new cool thing. I feel like this minimizes an important truth: that taking investment tends to mean losing control. Founders see that and want to maintain control.

mLuby 7y ago
That's why it's cool; coolness is value, independence, and self-control (lit. "keeping your cool").
- jagged-chisel 7y ago
  Sure, I get that. And it is cool. I just felt like the statement was a bit too reductionist. Enough so to make the comment.

ganeshkrishnan 7y ago

I feel like an in-between/better option than bootstrapping or VC investment is going for an accelerator or incubator. You get the all important human connections, a bit of elbow room for money and a nice way to interact with other fellow founders. It still is a bit of stretch to get into an accelerator especially if you are before product market fit or if the product is in an very "unsexy" space (like supply chain).

peterbell_nyc 7y ago
I've usually seen most accelerators as an onramp to a venture backed business. I've raised for a couple of startups and with one I went through an incubator and it was great. Right now, I work from home, have a 3 year old and just went all in on a very modest little lifestyle business. I can't imagine an accelerator being much help, and given my goals for the business, I'd be a waste of a slot in their cohort.
- algo_trader 7y ago
  Can u maybe share how much traction you had pre-accelerator and how much traction u had before a bigger seed/SeriesA ? My perception is at an accelerator or a $100K angel is really basically a nice pitch + MVP + some token revenue or customer maybes. I get it that if u are building yet-another-analytic-service, then the bar is higher.
algo_trader 7y ago
> bit of stretch ... accelerator.. before product market fit I dont get this. AFAIK accelerator is like ~$50K-$150K. What kind of product fit can u possibly reach before your first $50K ? Even a fully functional MVP only really shows basic execution ability. No?

carlisle_ 7y ago

This blog post seems more like a marketing grab with generic platitudes than it does genuinely helpful advice.

tnolet 7y ago
yes, it's copy & paste content littered with ads...
dplgk 7y ago
Like "For the first time in 40 years, the tide is starting to change". Says who?

goatherders 7y ago

"Build a business where you can do most tasks yourself" That is literally NOT a business.

zemvpferreira 7y ago
Underrated comment. I have nothing against bootstrapping but a business that you can’t easily sell or get away from, where you have no leverage on or ability to fully delegate is closer to being a job than it is a business.
- goatherders 7y ago
  Somehow my original comment got downvoted, which is bizarre. I can only guess it offended someone that thinks "creating work = creating a business." There is NOTHING wrong with creating work for yourself if you get paid for it. Half of my time is spent consulting and that is not a sellable or delegateable "business." It's me selling my time. Lots of people do that and it is fine. But starting a venture where you keep your arms around all of the critical tasks is not building a business. A business is a set of systems and processes that can be performed, managed, and recorded without reliance on a single individual.

gramakri 7y ago

Small typo. "Business is a discipline, you’re in it for the long hall". It should be "long haul".

danvoell 7y ago
No, I think he means he is in it so that he can buy a house with a long hallway. :)
- whycome 7y ago
  'Long hall' just gives me visions of death metaphors and "light at the end of a tunnel"
helpstay 7y ago
Thanks for pointing out the typo, fixed now :)

jiveturkey 7y ago

worthless article ... if you believe the title. this has almost nothing to do with bootstrapping per se. i don't know if the author is confused about it or just trying to draw clicks. decidedly untrue statements like 'For the first time in 40 years, the tide is starting to change' and 'when starting an enterprise' don't help. the fact that the specific business being discussed is almost certainly not one that could attract VC money anyway also doesn't help the author. a title that would make this article more reasonable is 'from side hustle to a viable one-man business in 6 years'. well, it's not specifically about side hustles either but it is reasonable albeit generic advice for one-man shops (possibly with some replaceable helper employees), for niche services such as skylight installer, gutter installer, ikea assembler, or as in this case, a subscription based marketplace for very tiny yet viable markets that can't be serviced adequately by large platforms.