My guest today is Nick Keegan, co-founder and CEO of Mail Metrics, a company helping highly regulated industries—like banks, insurers, and pension providers—communicate more effectively with their customers.

Nick started Mail Metrics in 2013 at just 24 years old, after serving 11 years in the Irish Defence Forces. It took 7 years to reach €1M in revenue, but what followed is nothing short of remarkable: in 2023, the company hit €40M—and is on track to do €210M in 2025.

In this episode, we go deep into the gritty early years, how he closed his first clients after 3 years of trying, and how Mail Metrics scaled through a combination of organic growth and strategic acquisitions.

Nick breaks down what he looks for in an acquisition target, how deals are structured and financed, and what it really takes to integrate teams post-deal.

We also cover:

• The challenges of selling into regulated industries with long sales cycles
• How Nick brought on a private equity partner while keeping control
• The key lessons from growing a 600-person company
• His approach to capital allocation, leadership, and leverage
• And the mindset shifts that helped him grow from a bootstrapped founder to leading a 9-figure business

Whether you're an operator, investor, or aspiring acquirer, this episode is packed with insight.

I hope you enjoy this conversation with Nick Keegan.

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Timestamps:

00:00:00 - Intro

00:00:11 - The early days of Nick and MailMetrics

00:07:01 - The story of the first two massive clients (took an extremely long time to close)

00:08:06 - Growth through acquisitions

00:11:07 - The story of the first two acquisitions (financing and structure)

00:16:16 - Post-acquisition strategy

00:19:05 - Timeline of all the acquisitions

00:20:09 - Improving the bottom line through synergies across the portfolio

00:22:59 - The third acquisition almost doubled the business 00:26:00 - 2–3 factors that need to be true for Nick to acquire a competitor

00:28:27 - When acquisitions don’t go as planned… 00:32:45 - The decision to partner with a private equity firm 00:37:15 - Nick and his roles over the years

00:41:48 - Nick’s view on leverage when doing acquisitions 00:43:40 - What Nick would do if he were to start all over again

00:46:35 - MailMetrics today

00:48:35 - Your goals can come true—sometimes 10x bigger than you ever dreamed

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Follow Mikk/PrivatEquityGuy on Twitter: ⁠⁠https://x.com/PrivatEquityGuy⁠⁠

Nick on X: https://x.com/Nick_Keegan

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.