EP105: Great by Choice and Other Lessons on Leadership

May 5, 2022

Digible recently celebrated its fifth birthday, and throughout this five-year journey, we’ve learned quite a lot about running a startup, building a fantastic work environment, innovation, thought-leadership, and more. We dedicated this episode to diving into some of the lessons we learned over the years. Joining today with the podcast are David Staley, president and co-founder of Digible, and Reid Wicoff, founding partner of Digible.

In any business venture, hard work can contribute to its success and growth. However, luck can contribute to defining the path of an organization as well. We start the conversation by talking about how these two factors come into play in a business venture. Another area we touch on is the concept of "Fake it till you make it." Over the years, we’ve seen many startups in the tech space following this sort of philosophy in their early years of business. We have also seen a fair amount of businesses getting in trouble as a result of this sort of thinking and discuss the sustainable growth of a business venture.

Over the last few years, we’ve seen the downfall of quite a few startups that quickly grew into the ‘unicorn’ status. We talk about some of these startups, some traits they had in common in terms of leadership, and what contributed to their untimely fall. Towards the end of the episode, we dive into what a business should do when they reach a point where they’re running out of cash and how to scale.

[02:15] Luck & Hard Work – Kicking off the conversation, Reid shares his take on the roles played by hard work and luck in the path to success of an organization.

[05:58] Advice for Startups – David shares some of his learnings from the five-year journey of Digible.

[11:44] Fake It Till You Make It? – Reid’s take on the implications of working based on the ‘fake it till you make it’ concept and whether businesses should embrace that concept in some cases.

[19:18] Failed Unicorns – We talk about some examples of failed startups that used to be worth billions at some point, including WeWork and Theranos, and the role leadership played in their downfall.

[27:18] Ensuring Longevity – How the leadership roles of a startup should be arranged in a way that improves its longevity.

[30:24] Running Out of Cash – David shares his advice on what to do if a startup is in a situation where it looks like the company is burning through cash for too long without getting enough traction.

[37:00] The Great Game – David shares some of the strategies he learned from the book ‘The Great Game of Business.’

[46:10] Mediocrity – How mediocrity affects the growth of a startup and how organizations should deal with it.

Resources
Great by Choice: Uncertainty, Chaos, and Luck—Why Some Thrive Despite Them All goodreads.com/book/show/12675109-great-by-choice
The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses goodreads.com/book/show/10127019-the-lean-startup
Lean In: Women, Work, and the Will to Lead goodreads.com/book/show/16071764-lean-in
The Great Game of Business: Unlocking the Power and Profitability of Open-Book Management goodreads.com/book/show/138298.The_Great_Game_of_Business
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