
← How They Scaled It4 Sept 2025 · 45 min
Building Trust Then Building the Brand w. Scott Kveton
<p>In this episode of How They Scaled It, I sit down with Scott Kveton, Co-Founder and CEO of CaseMark, who has a track record of building companies that define categories. </p><p><br /></p><p>Scott shares how intuition, scrappiness, and relentless customer focus shaped his journey, and why AI is set to transform legal tech in the same way the iPhone reshaped mobile.</p><p><br /></p><p>00:00:13 – Scott on brand-building struggles and leaning on experts</p><p>00:00:52 – Courtney introduces Scott’s career journey</p><p>00:01:39 – The three T’s: team, tech, timing</p><p>00:03:06 – Learning to trust your gut as an entrepreneur</p><p>00:04:28 – Investor skepticism and TAM projections</p><p>00:07:08 – Urban Airship’s scrappy early launch</p><p>00:09:26 – Lessons from Twilio’s Jeff Lawson</p><p>00:12:18 – Why legal tech? The problem CaseMark solves</p><p>00:14:39 – Starting small with “easy buttons”</p><p>00:16:47 – Why AI will increase litigation</p><p>00:20:59 – Simplifying the product for attorneys</p><p>00:23:32 – Scaling medical chronology automation</p><p>00:26:34 – CaseMark’s subject matter advantage (Scott’s wife as advisor)</p><p>00:29:18 – The future of AI collapsing tools in legal</p><p>00:30:04 – Scott’s evolving leadership style</p><p>00:34:46 – Branding lessons</p><p>00:38:59 – Advice for legal tech founders</p><p>00:42:12 – What Scott wishes he knew at CaseMark’s start</p><p>00:44:19 – Where to find CaseMark and connect with Scott</p>