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Failed for the past 12 years as an tech entrepreneur

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Re: Failed for the past 12 years as an tech entrepreneur

#52
post #21

I'm 16 years in and have followed a similar path. I graduated college in 2004, started my business in 2005 and never took a job. Consulting has gotten me here and I've had up to 4 direct hires with me, but my dream has always been to run a product business. I must have attempted 3 dozen different ideas by this point. But on Friday last week, we reached our 100th subscriber. Combined with other free products, we now h…

This is an underrated path, IMO.

Consulting is an excellent way to hone the non-coding skills necessary for bootstrapping a company: Scoping projects, timeline estimation, choosing tradeoffs, finishing things, selling things, presenting products to others.

It's also helpful to be able to get out and talk to other businesses and people on a regular basis. Bootstrapping can be extremely lonely in a way that is hard to understand if you've only ever worked inside of companies with people to talk to.

Re: Failed for the past 12 years as an tech entrepreneur

#53
Be sure to pay homage regularly to the gods of chance. Randomness plays a huge role in success and failure in all fields, but especially in entrepreneurial ventures. If you live in a developed country, relax and enjoy the fact that failure rarely means actual death.

Re: Failed for the past 12 years as an tech entrepreneur

#54
post #21

I'm 16 years in and have followed a similar path. I graduated college in 2004, started my business in 2005 and never took a job. Consulting has gotten me here and I've had up to 4 direct hires with me, but my dream has always been to run a product business. I must have attempted 3 dozen different ideas by this point. But on Friday last week, we reached our 100th subscriber. Combined with other free products, we now h…

This is an underrated path, IMO. Consulting is an excellent way to hone the non-coding skills necessary for bootstrapping a company: Scoping projects, timeline estimation, choosing tradeoffs, finishing things, selling things, presenting products to others. It's also helpful to be able to get out and talk to other businesses and people on a regular basis. Bootstrapping can be extremely lonely in a way that is hard to…

VCs actively dissuade founders from doing professional services.

Re: Failed for the past 12 years as an tech entrepreneur

#55
post #32

Manage your reputation very very carefully. I do tech for an email security service and we start blocking these very quickly once we see any anything we don't like.

Can you elaborate more on this? I think we are getting blocked :|

A link shortener is a simple way for malicious or spammy email senders to cloak their malicious or spammy link in something which is not yet on a block list.

So what we find is that as new ones come into the market they are eagerly adopted and we start to see evil links. From our point of view the earlier we put in place a wholesale block the better, because otherwise they may become "too big to block" like bit.ly etc... Although even these are blocked by gmail from time to time (for example).

Re: Failed for the past 12 years as an tech entrepreneur

#56
I had a corporate job for 9 years, did some freelancing on the side until I got a big client. Now I have a team of close to 20 people, a few good clients (referrals work wonders) and a MRR of 110k after 6 months. I have jumped into entreneurship making also a salary increase from a good corp job. I am saying this because for me consistency and incremental reputation and skills building has been extremely rewarding. There is a culture of leaving jobs fast over here and sometimes that is the right thing to do, but sometimes it is more rewarding to build a carrier over a few years before making the jump. Just consider your options and take the time, not everything needs to go super fast.

Re: Failed for the past 12 years as an tech entrepreneur

#58
post #54

Earlier quoted context omitted.

This is an underrated path, IMO. Consulting is an excellent way to hone the non-coding skills necessary for bootstrapping a company: Scoping projects, timeline estimation, choosing tradeoffs, finishing things, selling things, presenting products to others. It's also helpful to be able to get out and talk to other businesses and people on a regular basis. Bootstrapping can be extremely lonely in a way that is hard to…

VCs actively dissuade founders from doing professional services.

VC’s don’t want you distracted from their one shot at your next 18 months. They’d rather you go for broke and flame out rather than building a 5-year runway that allows you to slowly tune your ideas.

Neither is better than the other, but one might be better for a given situation.

Re: Failed for the past 12 years as an tech entrepreneur

#59
I’m sincerely not trying to be mean, but it’s possible you were previously simply bad at entrepreneurship.

There is this dominant narrative that entrepreneurship is primarily about raw willpower and persistence despite the odds. As a 20+ year entrepreneur I do not believe this to be the case.

I believe the primary skill is observation. Yes, we need to try different ideas, but what really makes a product work is listening to the market and identifying opportunities to create value. You’re not fixed on a product/solution ahead of time, but are just paying attention to needs and how those needs intersect with our unique abilities to create value.

When this is working well, it looks like luck. Over time we develop multiple viable business options and we get to choose the very best ones. Instead of a slog, success comes relatively easy.

Re: Failed for the past 12 years as an tech entrepreneur

#60
post #54

Earlier quoted context omitted.

This is an underrated path, IMO. Consulting is an excellent way to hone the non-coding skills necessary for bootstrapping a company: Scoping projects, timeline estimation, choosing tradeoffs, finishing things, selling things, presenting products to others. It's also helpful to be able to get out and talk to other businesses and people on a regular basis. Bootstrapping can be extremely lonely in a way that is hard to…

VCs actively dissuade founders from doing professional services.

Sure! If you're dumping a bunch of capital into something, you want to see that capital put to work immediately growing something to scale-- not for founders to be worried about stretching the capital by picking up nickels off the street.

That is, being capital efficient is good, but being distracted by other non-core things excessively to try and conserve capital is bad.

But that doesn't mean that bootstrapping with a consultancy isn't a viable path. It's only when you do it when you have capital sitting around that's not put to good use that it's a problem.

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