You can bootstrap your business to scale, but you'll have to make your own luck. Nobody knows this better than Mailchimp's Ben Chestnut. He used a DIY ethos to grow a $600M company without ever raising a dollar of outside funding. The Mailchimp story is the exception to Reid's rule (always raise more money than you think you need!). The episode explores a range of options for those who don't fit the VC-funding mold. Cameo appearances: LeVar Burton (Star Trek, Reading Rainbow, LeVar Burton Reads), Don MacKinnon (Milq), Karen Cahn (iFundWomen). Read a transcript of this interview at: https://mastersofscale.com/ben-chestnut-the-case-for-bootstrapping/ Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

If you try to avoid risk, you actually risk total failure. Or worse: mediocrity. Take it from Shellye Archambeau. She led the most stunning Silicon Valley turnaround you’ve never heard of. She took the role of CEO for a failing tech company, months from bankruptcy. Through a series of calculated risks, she led it through a complex merger, a head-spinning pivot, and grew it into MetricStream, which now boasts 1,200 employees and a valuation in the hundreds of millions. How? Clear goals and big risks — the same principles that have defined her career. With a cameo appearance by poker champion Liv Boeree. Read a transcript of this interview at: https://mastersofscale.com/shellye-archambeau-take-bigger-risks/ Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.