I made a cheat sheet to summarize the most important takeaways for you below.
Enter your email below, and I’ll email you a nice PDF so that you can save it.
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.