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

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 are 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.  

You can watch this episode below or listen on Apple Podcasts, Spotify, Google Podcasts, or wherever you get your podcasts.

In this episode we cover the following:

2:09 - Darby intro, Senior Engineering Manager at GitLab and co-founder of Lead Honestly

2:50 - Shay intro, VP of platform strategy at Active Campaign and co-founder of Lead Honestly

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 (and have used successfully in their day jobs), and how that has given them sharp opinions about their product features/experience.

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?

1:09:20 - Leaning on values to come up with pricing.

1:11:09 - There’s B2B2C (e.g. white label solutions that businesses turn around and sell to consumers). But perhaps Lead Honestly and similar companies are B2C2B businesses, meaning they sell first to consumers inside companies that then compel the organization to want to buy a license.

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.

1:14:55 - Where can people learn more about Shay and Darby and Lead Honestly? https://www.linkedin.com/in/shayhowe/, https://www.linkedin.com/in/darbyfrey/, https://leadhonestly.com/