Lessons learned from starting companies.

Seth Goldstein
Apr 2, 2014 · 6 min read

Entrepreneurship is creating products to solve important problems; and then identifying and recruiting people that can turn those products into sustainable businesses.

Summer, 2017:

I can’t say that I have always been a successful entrepreneur, but I have indeed been an entrepreneur for as long as I can remember.

What does it feel like? Like being on a ledge, somewhere deep in the pit of my stomach; a place where I need to feel my foot slightly over the lip in order to feel alive, but where it’s also hard to feel satisfied enough to step fully down.

And so I rattle forward deeper into the ideas until they become somebody else’s reality. At which point, I recoil in horror at the lack of an edge. So I push off away, somewhere else, to a place that nobody else has gone before, where I can feel at ease with the unique identity of my own ideas. These ideas are in many way what makes me me, or at least make me feel like me.

Serial entrepreneurs, repeat founders, those that keep starting up new companies, are a particular breed. My friend Mark refers to them as the ones with “crazy eyes.” We are like sharks that need to keep moving to stay alive. Our condition is no more blessing than curse. Just is the way it is. Always tinkering, always wondering “what if?”, always eager to get feedback so long as it’s not so affirming that it feels like they are blowing smoke up your ass.

The world is orienting towards increasing optimization. We are training the algorithms of the global, connected AI brain to need us less and less. Scratches, hesitations, curiosity, noise, and genuine cluelessness, remain beyond the machine to model. At least for now. Perhaps long enough for us entrepreneurs to make everybody else feel what it’s like to step over the edge, one more time.


1. Insecurity drives me.

2. I used to think i was afraid of failure, now i think i am more afraid of success.

3. I am never successful, but i always soon will be.

4. If I knew enough about the market I was disrupting, I doubt I would have the patience to do so.

5. We get old, our kids grow up in front of us, our relationships mature and take unexpected directions, some ebb away

6. All we have is our ideas, our emotions, our ambitions, our relationships, our time, our attention.

7. I am 47. Most of the people that I work with are in their 20’s.

8. What will my teams remember about me? That I was real. That I was a visionary. That I was early. That I was too easily distracted.

9. The CEO’s job is to be anxious when things are going too well, and relaxed when things are going too badly; like a shock absorber.

10. Money is not the goal, it’s a means of helping you work on what you want, when you want and with whom you want.

11. I doubt that I will ever give up trying to create new things.

12. When I am unsettled, i tend to make impulsive decisions.

13. I used to be too impressionable and tended to overreact to the most recent feedback.


1. start a company when you imagine a solution that feels more and more inevitable to a problem that seems to be getting bigger and bigger

2. keep your head up, and make people laugh. if you are not approachable, you will not get valuable feedback. mbwa = management by wandering around

3. whether expressing or denying our emotions, they drive our actions.

4. put people in the right roles, surround him or her with great people, and focus them on a meaningful goal

5. your company is an expression of your desire to create something bigger than yourself

6. teach people how to use their unique skills to create something new.

7. if you are at ease and confident in your decision, why ask for feedback? you will get some, and then you will frustrate the person who gave it to you.

8. follow your vision with absolute conviction, but make sure you listen for advice on how to get there.

9. the right time to have that difficult conversation is now.

10. make sure your team feels comfortable enough to tell you the things that they think you don’t want to hear.

11. delegate, don’t abdicate.


culture is like concrete: if you wait too long to set it properly, it will be impossible to reset later on
  1. make employees feel like owners
  2. titles cost you nothing, but its dangerous to over-inflate them
  3. establish SMART goals: specific, measurable, achievable, realistic and time-based
  4. why not refer to your early team as co-founders?
  5. allow team members to award each other stock: it enhances the feeling of ownership and clarifies where respect is earned in the org
  6. some of your early co-founders will not be around for your later co-founders. that’s natural.
  7. if you do culture right, you won’t have to ask your team to work hard. but you will need to help them prioritize.


  1. hire people based on three criteria: do they have unique skills? are they willing to do what’s necessary to win? are their values in line with yours?
  2. B players turn A players into B players: remove B players.
  3. take chances on people who have big chips on their shoulder: failing, being doubted, needing approval, etc.
  4. the ideal team is big enough to build anything you want, but not so big as to be able to build more than you need.


  1. there is nothing like numbers to ruin a good story.
  2. it’s not about the money, it’s about the money.
  3. raise money when you can, not when you have to.
dress british, think yiddish
  1. focus on the individual who is going to be involved, not the firm’s name.
  2. unless you are exiting, don’t over optimize around valuation.
  3. startups fail because they run out of money.
  4. in a bull market, lucky people think they are smart.
  5. smart people know how to get in positions where will likely get lucky.


  1. make a product that gets your users to smile.
  1. a successful interface and interaction model will permit you to add features over time without complicating the experience.
  2. find an exceptional creative developer, give him the support she needs, and challenge her to build something that she will be proud of.
  3. as reid hoffman says, if you aren’t embarrassed by your first version then you waited too long to release it.


  1. Don’t be an arrogant asshole. (Anonymous)
  2. Swallow a lot of coal to shit a diamond.
  3. Tell them what you are going to tell them, them them, tell them what you told them.
  4. Starting a business and achieving market fit is like robbing a moving train because you have to know where the market is going and you have to be able to get there in time.

- fin -

Seth Goldstein

Written by

Mission-Driven Entrepreneur. CEO of Spartacus. More on me at www.sethgoldstein.com

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