SJ26 – The Healthy Uncomfortable and Scaling Your Startup

a.k.a. “We Promise It Won’t Be Boring”

Don’t miss our latest round-up episode, answering your questions, expounding on your conversation starters, and delivering David Bowie tributes. We may also have snuck in some Alan Rickman references.

Still want to join in? Send us your thoughts on how this quote applies to you:

“All my big mistakes are when I try to second-guess or please an audience. My work is always stronger when I get very selfish about it.” – David Bowie, The Word, 2003

Previously aired on 1/19 at 3 pm ET/12 pm PT

Links and Highlights:

Teague as a blonde? The end of the world? There’s a lot going on this week.

The Healthy Uncomfortable

  • “There’s somewhere in between the comfort zone and the terror zone, where you have to have some courage to try the new thing.”
  • New t-shirt idea: “No matter the question, time-boxing is the answer.”
  • “The question to ask oneself is, ‘What are the ways in which I’m intentionally making myself uncomfortable?'”
  • “Being vulnerable over being polished holds people back the most…. If you don’t feel safe in vulnerability, you’re never going to make any changes or push in any uncomfortable directions.” Also known as: “I get knocked down, I get up again. You’re never going to keep me down.”

Advice for early-stage entrepreneurs and start-ups in the scaling phase:

  • “In addressing an entrepreneur’s most important early-stage question – customer acquisition – it’s easy to waste a lot of money in the wrong channels, especially if you’re not taking a measured approach… How do you know if a channel is working for you or not?”
  • “You can Lean Startup your way through that question by being methodical about it and keeping the costs low by doing it on a pragmatic level. If someone’s selling clothes, for example, I’d go out with 25 t-shirts and see if 25 people will buy them.”
  • “We’re not getting scientific proof; we’re getting down to, ‘Is moving forward on this product or business a reasonable bet to make?'”
  • “Do you have the kind of business that can be advertised, or does it have to be pounding the pavement? Customer acquisitions costs are different depending on the industry.”
  • “Customer acquisition costs will change in different channels all the time, and you have to know when there are diminishing returns in those channels.”

Jason is sharing the story of Mostafa Hassoun, a 23-year-old Syrian refugee now in Annapolis who is hoping to enroll in community college. Take a moment to learn more about him and consider donating to help him rebuild his life after experiencing great tragedy:


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