78 minutes | Oct 6th 2020

Starting a side business, validating a product idea, and managing people :: the Lead Honestly story with Shay Howe and Darby Frey

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In this episode of Ventures we examine the origin story of Lead Honestly, a web-based software platform designed to help managers have better one-on-one meetings with their direct reports. My guests Shay Howe (https://www.linkedin.com/in/shayhowe/) and Darby Frey (https://www.linkedin.com/in/darbyfrey/) have a frank and open conversation about starting a side business, balancing family life and their day jobs, transitioning from builder to manager, validating their startup idea, holding to values when setting pricing, and advice for entrepreneurs.Importantly, Shay and Darby are two of the people I respect most in the world when it comes to being “product people”; i.e. those with smart and relentless focus on the customer and the ability to translate that focus into a world-class (and lean-startup friendly) product and consumer experience.  Visit https://satchel.works/@wclittle/ventures-episode-13 for detailed notes and links to resources mentioned. You can watch this episode via video here. In this episode we cover the following: 3:54 - What does Darby do, day-to-day, in his day job? 6:04 - What does Shay do, day-to-day, in this day job? 9:31 - When did Darby start writing code?11:08 - Shay’s shout-out to Darby on being an entrepreneurially minded engineer, i.e. shipping value to customers. 12:24 - Will’s story of watching a master's thesis from someone very excited about optimizing an algorithm (and why these kinds of people are important/needed, but they are often different than an engineer wired to be customer-minded). 13:02 - How did Darby transition from writing code to becoming a manager? 15:09 - What advice would Darby have for an early stage startup CTO looking to hire their first engineer? 17:20 - What is the origin story of Lead Honestly? 22:52 - How did Shay/Darby go about testing/validating the idea to decide to give it a go?27:00 - Once initially validated, how did Shay/Darby go about growing the company and juggling the day jobs, family life, etc…  30:38 - Darby highlights the importance of using their own product 32:00 - Shay highlights that the origin story was born out of a real problem that both Shay and Darby experienced themselves. 37:35 - Darby emphasizes their holistic approach to focusing on the customer problem and building/iterating features from that perspective. 38:20 - What should an “idea person” do who isn’t technical or a “product person” go about building a company from scratch? 45:08 - The importance of Product-Market Fit, Founder-Product Fit, and Channel-Product Fit. 46:17 - Tips for validating an idea that overcomes (understandable) biases. (Check out the book: The Mom Test)52:43 - How did Shay and Darby balance their product vision and feedback from early customers that might point in a different direction? 56:10 - Once you know you “have something” - how do you go about actually building the product? What are the nuts and bolts of the build process? 1:02:22 - What is the vision for the short-to-medium future of Lead Honestly? 1:05:55 - Where does Lead Honestly fit in the spectrum of Business to Business (B2B), Business to Consumer (B2C), and marketplaces for software startups? 1:11:50 - Final words to entrepreneurs and early stage investors listening in, especially founders trying to juggle a day job and a side business.
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