Conclusion and Cheat Sheet

Adam Guild, Co-founder of

About Adam Guild

Adam is the co-founder and CEO of He is also a proud high school dropout turned Thiel Fellow and Forbes 30 Under 30 honoree.

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I made a cheat sheet to summarize the most important takeaways for you below.

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Should I join a startup?

  • If you’re optimizing for work-life balance or short-term cash comp, no.
  • If you’re optimizing for learning faster and long term wealth, yes.
  • The key is in joining the right startup. Not all startups are created equal.
  • If you pick right: you can get wealthy, learn faster, and enjoy work more.
  • Many legends in tech started as startup employees: B Armstrong, M Mayer, D Sacks.
  • Lasting employees 1 to 100 at Google, Stripe, and Facebook made $10,000,000+ each.

Which startup should I join?

  • If you’ve decided that you want to join a startup, it’s critical that you pick the right one.
  • Most startups fail, but the few that really succeed create massive wealth for early team.
  • Don’t start with startups with an open role that you want. Start with the best startup.
  • The best startups are always hiring A+ people who can help, regardless of openings.
  • How do you evaluate startups? Think like an investor.
  • Except rather than money, you’re investing your most valuable resources – time.
  • The best early investors tend to make investment decisions based on team and market.
  • Team: world class startups are built by world class teams.
  • Market: world class startups are built in large or rapidly growing markets.
  • Evaluate the founder(s) to evaluate the team.
  • YC criteria for founders: extreme determination, high intelligence, high resourcefulness.
  • “Startups become the team they build, not the plan they make.” - Vinod Khosla
  • Look at the quality of the team: are they intimidatingly great in some ways? 
  • Learn the founder’s life story, and look for evidence of extraordinary ability. 
  • Study cofounder relationships, as this is a top risk factor. Are they aligned and close? 
  • Pick a company which will have a strong alumni network for the rest of your career.
  • “When a great team meets a lousy market, market wins.” - Andy Rachleff 
  • Great markets are: large and still fragmented OR small but will be large.
  • Flexport = example of great company in a large and still fragmented market.
  • Google = example of great company in initially small but now huge market.
  • Network effects help. Does each user make it more valuable for other users? 

How to join a startup?

  • Don’t just apply on the job board and sit back waiting.  
  • Busy startups are chaotic and noisy. You need to break through the noise to be noticed.
  • Startups want people who take massive action and get things done, demonstrate that.
  • Do the job before getting the job: figure out how you would help and create a plan.
  • From there, contact the startup. Send a personalized email to the relevant founder.
  • If they don’t respond, keep following up until they do. Persistence pays. 
  • Good impressions on interviews start with good energy and a good mindset. 
  • If you feel nervous, you can instead choose to interpret it as excitement.
  • Shift your mindset: they need you more than you need them. 
  • Founders spend hours every week searching to find people like you.
  • Recruiting excellent talent is the most important thing that founders do. 
  • Know the customer, product, and market context going in. Research ahead of time.
  • Interview them as much as they interview you.
  • “I would love to start by learning more about you and Owner. Does that work?”
  • Prepare your questions ahead of time: ask about things that you can’t find online.
  • Use your questions to get the “cheat codes” on what the founder is looking for.
  • Come prepared to that interview with a solution to a problem the business is facing.
  • Share your solution in that first conversation.
  • Negotiating Startup Compensation 
  • Hold off on discussing comp expectations until after you’ve each determined fit.
  • Don’t lead with sharing comp expectation, lead with sharing value.
  • Research ahead of time using Pave or Payscale what average comp looks like.
  • If you each want to work together, you be the one to anchor comp expectations.

How to succeed after joining a startup?

  • Figure out the company’s top priorities.
  • Talk to team and customers to find. They are often in unsexy parts of the business.
  • Create a success plan for yourself, to align expectations. 
  • Share how you contribute to the mission, your top priorities, and 30/60/90 day plan.
  • Focus on A Class Problems (high impact, usually high difficulty).
  • Execute your plan. Ruthlessly prioritize the top 3 things you must do, and stick to them.


  • Anthony Chen (employee #1 at Flexport)
  • Micah Bennett (employee #1 at Zapier)
  • Jack Altman (cofounder, Lattice –team building expert)
  • Jed Somers (founding operations leader, Owner)
  • Robbie Crabtree (communication expert, early stage startup advisor)
  • Kyle Norton (first sales leader, Owner and League. Previously Shopify)
  • Cory Levy (Cofounder, Afterschool. Investor) 
  • Dean Bloembergen (cofounder and CTO, Owner)
  • Julian Shapiro, for all that he has taught me about content and for being an amazing friend and investor and for inspiring many of the style elements of this blog.

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Co-founder and CEO at, helping restaurant owners save their businesses. high school dropout but lifelong student. Thiel Fellow. Forbes 30 Under 30.

Adam Guild, Co-founder of

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