Book Cover
Lost and Founder

★ ★ ★ ★ ★

TL;DR: Extremely transparent and valuable perspective of a 15-year startup CEO who has been through it all.


1: The Truth Shall Set You Free (From A Lot Of Shitstorms)

  • One of the biggest things I’ve learned about startups: it’s dangerous to go alone. (2)
  • 50% of companies that last 4 years go under (Berkeley)
  • Every email and convo should be conducted as though it will be leaked
  • Done with the pain of secrecy, happy to trade it for the challenges transparency brings

2: Why The Startup World Hates on Services (And Why You Shouldn’t)

  • Effective product-focused business needs reach (influence a large audience) and scalability (revenue grows quicker than costs) (35)
  • Gross margins on software products: 75-80%
  • Gross margins on consultancy: 25-40%
  • Multiplier for services: 1-2x
  • Multiplier for products: 3-8x
  • Services firms are often a superior financial deal for a founder

3: Great Founders Don’t Do What They Love; They Enable A Vision

  • Chapter title is great
  • Reset passion from “I want to do this work” to “I want to see something I create change the world in this way”, your expectations will align with reality (53)

4: Beware The Pivot

  • Find a market with incumbents that are a combination of:
    • Hated by customers
    • Unwilling or unable to evolve
    • Protected by competitive advantages you can unravel
    • In their early stages

5: Startups Carry Their Founders’ Baggage

  • Founder attributes instill themselves in the org
  • Every founder has a different take on the hardest parts of building a company. And those same founders will have different takes on the easy parts. Talk to two talented software engineers who founded a company and you may find that recruiting, managing, or marketing are perceived as the most difficult issues. Talk to the marketer and people manager who founded a company down the street, and you may hear just the opposite. The uncanny truth is that those “hardest parts” and “easiest parts” say less about the challenges and more about the strengths and weaknesses of the founders themselves. We all believe the problems and experiences we face are the most common ones, the ones every founder must struggle against. Availability bias. (78)

6: Don’t Raise Money For The Wrong Reasons Or From The Wrong People

  • Two reasons not to raise money: Odds and Cost
  • Get comfortable with the odds, or don’t roll the dice. The venture business is about outliers.
  • Founding to IPO takes an average of 11 years
  • Be very careful about raising money

7: So You’ve Decided To Ask Complete Strangers For Millions Of Dollars

  • Common stock: for you and cofounders
  • Preferred stock: investor stock (special rights like first-right-to-money or board seats)
  • Stock options: employee stock (buy stock at price it held when issued the option)

8: Founding A Top 5 Percent Startup May Not Make You Rich

  • A startup can be a great way to visibly multiply what companies are willing to pay to bring you aboard. It might be a great way to level up your skills. And it has the outside chance of making you remarkably wealthy. Just don’t go in blinded by the money.

9: Scalable Marketing Flywheels > Growth Hacks

  • Flywheel: takes time to get going, only after it rotates smoothly does it become friction-light

10: Real Values Don’t Help You Make Money (In The Short Term)

  • They’re not core values if you’re willing to sacrifice them in exchange for money. (140)
  • Unifying forces of values: shared commitment, set of blueprints for decisionmaking, evaluation criteria for retrospection
  • Culture > competency
  • Starting a company with friends is not additive

11: Living The Lives Of Your Customers And Their Influencers Is A Startup Cheat Code

12: Great Products Are Rarely “Minimally Viable”

  • Impact of reputation and word of mouth on potential success vs. the risks of MVP hangover is too important to ignore. (191)

13: Should You Sell Your Startup Early? Yes, Probably

  • Exits bring an almost mystical sense of closure and accomplishment

14: If Management Is The Only Way Up, We’re All F’d

  • Management is a skill, not a prize

15: Vulnerability Does Not Equal Weakness

  • Psychological safety predicts performance better than any other

16: Self-awareness Is A Superpower

17: Focus

  • The benefits of focus are too great to ignore, hidden only by the resolve needed to stay on target. (278)

Afterword: Cheat Codes For Next Time

  • Steps for validation:
    • Talk to individuals
    • Build landing page and validate