69: Sound, Actionable Advice with Jason Cohen


December 27th, 2018

1 hr 10 mins 43 secs

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About this Episode

Derrick is away, so Ben welcomes Jason Cohen, CTO of WP Engine and four-time entrepreneur. Jason knows a thing or two about startups and mentoring them to achieve profitability and growth.

Jason is a straight talker and tells it like it is to get to solutions sooner. He encourages bootstrap founders to find an advisor who aligns with their goals. You need to know how to take advice and use advice that is right for you and your business. Even if you get great advice, think for yourself!

Today’s Topics Include:

  • Advice is not enough; luck, execution, and other pieces are involved
  • Be honest and know what qualities investors want
  • Jason characterizes a company as a learning machine that’s constantly failing, not doing the right thing, and has no resources; but has agility to learn and react quickly
  • Embrace your humanity and smallness; don’t lie about being big
  • Share the good and bad about your startup journey for others to feel connected to and support it
  • When making decisions, apply filters to cut out things; constraints are useful
  • Universal Rule of Success: You’re all in and apply a lot of energy; makes you more productive and fulfilled
  • Many paths lead to success and failure; pick ones that naturally fit you
  • A good engineer can build features (not risky), but can they do everything else - probably not (risky); identify how a company’s priorities need to change to address risk
  • To be sustainable, get help and became an expert in something - not everything
  • Product success depends on use cases and maturity of company (convince customers how good it is now and will get even better); if product isn’t good, then business won’t last
  • Jason shares ideas and options regarding Ben’s Tuple product
  • When bootstrapping, getting money is challenging because you’re not on people’s radar

Links and resources:

WP Engine

A Smart Bear Blog

Can you bootstrap a company on the side? (Part 1 with Jason Cohen)

Jason Cohen - Designing the Ideal Bootstrapped Business

Capital Factory

Paul Graham


Peter Thiel





Silicon Valley Successes Podcast

Art of Product on Twitter

Derrick Reimer Website

Derrick Reimer on Twitter

Ben Orenstein Website

Ben Orenstein on Twitter