Hey, I'm Dan! I invest in early-stage startups at Madrona and write a weekly newsletter called the DL

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Starting a Startup from Microsoft

Last week at Madrona, we hosted a lunch and learn with our interns and Brian Saab, the CEO of Unearth, a modern mapping platform. He talked about his journey from Microsoft to startup CEO, and it was a really insightful session. Here are my highlights from Brian’s talk:

Microsoft is a great launching pad for starting a company. Why?

  • There is no shortage of people who want to leave and start a company
  • It’s a great training ground for learning how to run a business, build products, and manage teams
  • You have great visibility into product roadmaps and know what is valuable to large companies like Microsoft and its customers
  • There is a great network of Microsoft alums who want to help, invest, and join you

Three step process for starting a startup

  1. Get the team: Build your network of people who will self-select to join a startup. Look for people who are gritty, resilient, and want to take risks
  2. Get some customers: Invest $10-20K in high-quality mockups that you can show to potential customers and get feedback
  3. Get investment: Building relationships and conviction takes time, so meet with investors early and keep them updated on your progress

How is it going at Unearth?

  • We started with great customers in construction but over time found that the maintenance market is much larger than the new build market, and those customers have a burning need for our product
  • We’re raising money soon, so we are investing time building relationships with a targeted group of investors

Brian’s startup advice is spot on, and I especially love his tactical advice around investing in high-quality mockups to test your conviction in an idea. If you’re not willing to spend a little money on product development, why would someone else buy from you or invest in you?

I also thought Brian had a great take on Microsoft as a training ground for startup founders, and to make the case, here’s a quick list of companies from Kirby Winfield of companies founded by Microsoft alums: Zulily, Convoy, Rover, OfferUp, Docusign, Smartsheet, Outreach, Auth0, Zillow, and Expedia. Geekwire followed up this tweet by publishing an analysis showing that ~25% of the top PNW startups are run by CEOs who worked at Microsoft.

TL;DR – Microsoft is a great place for startup founders. If you have any friends at Microsoft who want to chat about starting a company, send them my way! (if there’s enough interest, I’ll organize a meetup!)


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