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I bootstrapped a $10 million company and need serious help

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Re: I bootstrapped a $10 million company and need serious help

#71
post #28

Earlier quoted context omitted.

An empty seat is better than the wrong person. This. So very, very much this. A bad hire at the executive level won't merely slow you down. You might lose ground, or possibly even crash and burn. I've seen it happen, and I'm sure I'm not the only person here who can say that.

"An empty seat is better than the wrong person." Perhaps at the executive level, but I'm not sure I agree with this as a general hiring strategy. This mentality might go pretty far to explain why there are so many companies that claim they can't seem to find enough talent, while un(der)employment is still high. Companies interview and interview, but are petrified of hiring "the wrong person" so they just keep on inte…

It's the equivalent of old school investing; sit on the money until a really really good investment comes along; in the mean time you miss lots of good opportunities because you don't have a good framework for managing risk. Angel investing changed all that. Maybe there should be a greater move to angel employing; a small commitment up front until traction is proved.

Re: I bootstrapped a $10 million company and need serious help

#73
post #28

Earlier quoted context omitted.

An empty seat is better than the wrong person. This. So very, very much this. A bad hire at the executive level won't merely slow you down. You might lose ground, or possibly even crash and burn. I've seen it happen, and I'm sure I'm not the only person here who can say that.

"An empty seat is better than the wrong person." Perhaps at the executive level, but I'm not sure I agree with this as a general hiring strategy. This mentality might go pretty far to explain why there are so many companies that claim they can't seem to find enough talent, while un(der)employment is still high. Companies interview and interview, but are petrified of hiring "the wrong person" so they just keep on inte…

The wrong person doesn't just produce less value than the right person, they can actively create negative value.

They can do shoddy work that negatively impacts the ability of other employees to do work, they can cause reputational damage to the company if they're public-facing, they can create a toxic work culture that disincentives other employees.

Re: I bootstrapped a $10 million company and need serious help

#74
post #63

Earlier quoted context omitted.

I'm surprised, it comes up frequently among programmers, and I know not all of them could have read that wonderful book.

I encountered it in the Jargon file first, and that was part of what prompted me to read Stranger in a Strange Land.

Ditto. I first encountered "grok" in the early 1990s. I read Stranger in a Strange Land for the first time this year.

Re: I bootstrapped a $10 million company and need serious help

#75

Wow! The quantity of bad advice in these comments is shocking, if not down right disturbing. If Intel, GE, or Mircosoft hired a consultant to advise them on the right move, the vast majority of people on HN would scream bloody-murder and speak about it as a perfect example of big-business and its stupidity. What hypocrisy! Ben, the reality is that you clearly have moved past Steve Blank's description of a start-up; y…

I think that your advice is itself pretty bad advice.

It is theoretically possible to hire someone like what you describe, but it seems vanishingly unlikely and much more likely to cause damage.

As many others have pointed out, each business is unique, and the fact that the OP has reached the level of success they've reached is proof that they have a fairly solid management team already. Most likely, they are falling prey to impostor's syndrome - "one of these days someone will discover I'm a fraud and don't deserve all this success".

The cure for that is not to give in to the impostor's syndrome, but to reject it by observing the simple evidence that someone who builds a $10m business in 2 years is clearly very talented and skilled.

Ultimately, if the OP doesn't want to run this business anymore, they could just sell it. But if they want to keep running it, there's no way to abdicate to some "adult supervision" that will magically make all the problems go away. It will just replace the problems with a different set of problems, specific to the new hire.

A better approach if the OP wants to keep running this company is to build some good relationships with mentors who can help the OP grow into the role.

Re: I bootstrapped a $10 million company and need serious help

#76

Earlier quoted context omitted.

one of your challenges is that at this point, anyone who is interested in helping you, is also the kind of person who wants to get rich off of your hard work (aka ownership in your company). not to say that they won't work hard themselves, but incentives are incentives. just be careful when you talk to private equity, investment banking and growth capital folks and do not give up ownership of your business easily, if…

wow, you totally called it! already got on the phone with someone wanting to take things over and do crazy things. shady people ;-) Thanks, i'll be careful. appreciate the advice. I've kept close control thus far and have not wanted to raise money. Hope the right person might come into the picture. Already happy to get a couple genuine emails. cheers!

What you're looking for is a mentor, not a hire. You need someone who's been around the block to give you pointers and illuminate your blind spots. You're clearly doing very, very well already and should be proud of it. Don't let yourself feel like an impostor. You're not. You've earned your success.

Re: I bootstrapped a $10 million company and need serious help

#77

Be careful not to throw out the baby with the bathwater. You're probably doing a better job than you realize. Try working with an executive coach - I work with Bryan Franklin. It's easier for you to develop leadership and management skills than it is for an outsider to really grok your business and share your vision. Regarding the marketing role, be sure to get the right kind of marketer: https://medium.com/on-startu…

sound advice, thanks a bunch. i just threw the executive titles out there since i think that's where they would ideally lead to, and i don't exactly know how to speak to the people we are looking for to help us. I will read the medium post you linked now! if you are ever in the bay area, hit me up, id love to meet for coffee.

Going with the "get good consultants/coaches" - if the coaches/consultants are good, and a good fit, then see if you can bring them on board.

Traditional "interview and put in place" hiring strategies are built around the needs of traditional large organisations with massive amounts of existing organisational momentum and plenty of time to recover from mistakes or retrain duff hires.

Small fast-moving companies don't have those advantages, and shouldn't hire that way. You're obviously innovative - don't forget to apply that creativity to your business processes.

Re: I bootstrapped a $10 million company and need serious help

#78
post #36

If I were in your position, I would apply to YC.

YC's 6% equity cut isn't a big hit when you're at the "we have an idea" stage, but if they're a $10M company already that's a lot to pay for advice...

I think it's worth evaluating. Increasing their chance for success by 6.4% isn't that high a hurdle. IMO, it's a horse race against all the other next steps OP could take with his business. YC's a pretty strong horse in that race.

(I suspect there's also still room for negotiation, even if YC isn't advertising that fact any more. Three guys and an idea? 6% More than $10MM in revenue? Let's talk.)

Re: I bootstrapped a $10 million company and need serious help

#80
I recommend looking into joining Entrepreneur's Organization. It's an organization of business owners who own businesses with revenue > $1 mil/year (there's also an "accelerator" with owners whose revenue is > $250K/year). They will provide invaluable coaching, insight and network that will help you take your company to next level.

There's a chapter in SF: http://eoaccess.eonetwork.org/SanFrancisco/Pages/default.asp...

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