Serial Founders: What is the one thing you wish you knew from the beginning?

7 votes

I will offer two:

Don't get out in front of your skis.  Only acclereate spending when you have locked in on your value creation metrics that you know you can drive with more spend.

Remember, you are also the communicator in chief.  You need to really focus on repeating and reinforcing the key tenants of your strategy.  You and everyone else at your company should be able to answer these questions in a similar way and off the top of their head.  What is your value proposition?  Who is your customer?  What are your values?  What is your culture? What is your mission?  What problem are you solving?  How do you make money?

6 votes

Focus, focus, focus.  We all start with lots of great ideas and tend to believe that the value is in the ideas, but few startups fail due to a lack of ideas, many fail due to lack of focus...

5 votes

I wish I knew: "that everything takes twice as long; costs twice as much; and is twice as hard as anyone who's done it is ever willing to admit". 

4 votes


Here is where it started:
Today, I own twelve sites that bring in six figures combined (i.e.,,...etc.). I bootstrapped and self funded the first one at age thirty-eight with only $32 to pay hosting server space. I did (and still do) all the ball busting code, copy, art, and production.
Here are the things I now know after eight years of running these online businesses that I did not grasp early:
1. People only buy two things: Solutions to their problems and/or good feelings.
2. The business is people. People only buy from people and money only comes from people.
3. Money does not care how it's spent, who owns it, or where it comes from. It's your responsibility.
4. Legal costs are just part of success and the business. The bigger the success, the bigger the litigation target.
5. Focus on high conversion. Low traffic and high conversion is cheaper and easier to maintain when you are flying solo.
6. Customers buy for their own reasons...not yours. Get over yourself.
7. Customers do not need your product...they have to want it. So, don't fall in love with your own site or app.
8. Building an online site or app is easy compared to the task of convincing a customer they should part with their money and hit the "Send Payment" button. 
9. This is Illinois. Stay up to date on the politics. Having an Amazon tax suddenly get passed and taking a sizable chunk out of your successful affiliate program is complete bullshit. Make a trip or two downstate to get some face time. Remember, the policies and parties cannot be changed, but your individual situation can be heard and likely accomodated. ;-)
3 votes

I would echo all the comments from the esteemed gentlemen, and just add that I wish I had known earlier how to tell a customer "no" when they asked for things that were out of scope.

1 vote

I wish I knew how to use equity to aquire the things I needed. Determining the right amount of shares for the right people in exchange for their help is very hard. I've solved the problem, however (

1 vote

Hire and fire well.  People are the reasons startups succeed or fail.

  • Great talent enables you to lead and focus on your vision.  Pay them well and make sure they have stock.
  • Trouble makers cause you to lose focus and put out fires.  They can be a cancer to the rest of the team and need to be removed quickly.
0 votes
  • That is a low-paid job.
  • That everybody is looking for the same senior developers.
  • That senior founders have smart lessons to teach you.
  • That you make a lot of mistakes.
  • That everybody is trying to SEO something
  • That everybody knows the words "lean", "conversions", "metrics" and only a few know exactly what they mean.
  • That programmers build MVPs without testing frameworks
  • That rich kids also complain developers are expensive. And this pisses me off.
  • That a lot of startups send you surveys even when Eric Ries tells you is a waste of time.
  • That the average startup founder is in their 20s, with little real life experience, wife-free, kid-free, willing to be a "Bud Fox".
  • That Paul Lee tells you if you are over 30 you are wasting your time
  • That there are weird crazy people out there that tells you "Sign my NDA or I won't tell you my idea".
  • That a lot of startups don't care what your startup does even if you explain it in plain english.
0 votes

Plan for what will go wrong, because at some point it will.  Vest everyone (things happen - even with best freinds).  Conserve your cash (it does take longer and cost more).

Interview everyone and ask questions you don't want to hear the anser to.  Our tendancy is to ask questions that lead down the path of why our idea is great.  Instead, find out the barriers to them buying and you succeeding.

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