Episode 2: The Ripple Effect of Creating a Solid Leadership Team: Kyle Mack of Middesk

Startup Growth Stories

Sep 6 2022 • 24 mins

About this episode:

Kyle Mack is CEO and Co-Founder of Middesk, Inc. Middesk helps companies onboard their clients faster by streamlining middle office processes. Using this approach, their clients (including Plaid, Checkr, and Truework) are able to onboard more customers, faster, while reducing compliance and business risk. Their vision is to apply these principles to every meaningful detail of every business. Doing so will improve decision-making across compliance, fraud, and underwriting by providing more relevant and complete information in areas of financial stability, legal exposure, and corporate relationships, among others. In this way, Middesk not only aims to reduce risk but expand economic opportunity to businesses that lack traditional measures of obtaining credit or financial standing.

In my conversation with Kyle, we’ll talk about his early days working in his father’s garbage business, breaking away from Checkr with his own business concept, and the many lessons he learned along the founding journey with Middesk that he hopes others can learn and benefit from.

Startup Growth Stories is hosted by Don Muir, CEO and Co-Founder of Arc Technologies. In each weekly episode of this podcast, you’ll hear from first-time, bootstrapped, and unicorn founders around how they secured their first customers, convinced their first employees to join, and grew their business. Founders and industry insiders share their greatest successes (and failures) and the things they learned along the way. In the final minutes of each episode, guests get vulnerable - they share very personal stories about the impact of their work on their wellbeing, their relationships and their families.

In this episode you’ll hear:

  • [00:57] Who is Kyle Mack?
  • [01:25] Middesk and the services it provides
  • [02:00] Kyle’s biggest inspiration has been his family, learning work ethic from father and grandfather who owned small businesses
  • [02:50] The Evernote on Kyle’s phone – he has ‘journaled’ all the ideas and questions and discoveries along the way in the journey of founding Middesk
  • [03:55] Where the idea for Middesk came from, and meeting Kurt Ruppel, his CTO and Co-Founder
  • [05:17] The problems Kyle knew could be solved with a company like Middesk
  • [06:22] Kyle’s support network early on included pros from Instacart, Checkr, and more
  • [07:44] With $75M in financing, 80 team members, and over 300 customers, what Kyle learned along the way with respect to fundraising
  • [11:28] The most important part of building your business foundation is the network of people you build around you
  • [13:30] Kyle’s advice for first-time founders, and what he would have told himself early on
  • [15:26] Some specifics – the foundational operating principles at Middesk
  • [17:30] How Kyle has stayed optimistic, not focusing on the negative emotions, leaning on your network of support, getting a coach
  • [19:05] The impact of being a founder – mental and physical health
  • [20:31] Lessons learned: Get a coach early on, realize the ripple effect your hiring of the first few people will have, keep your internal story tight and focus on your main deliverables
  • [24:00] It has been the most difficult and challenging process of Kyle’s life, but would he do it again? Yes!

About Kyle Mack & Middesk

CEO and Co-founder of Middesk, (YC W19) a Saas for business verif