#98 3-time founder Craig Walker — From Selling Door-to-Door to 3-time founder; Building Google Voice; and the Real Trade-offs of Entrepreneurship
Description
Craig Walker is the founder and CEO of Dialpad, a business communications platform powered by AI. A former M&A lawyer turned serial entrepreneur, Craig previously co-founded GrandCentral (acquired by Google and relaunched as Google Voice) and sold his prior company to Yahoo. In this episode, Craig shares how his career unfolded from door-to-door dictation sales to running a 1,500-person company, and how AI became central to Dialpad’s strategy long before the hype cycle.
Craig opens up about the loneliness of leadership, his bet-the-company acquisition of TalkIQ, and the hardest day of his career when four high-stakes deals all hinged on one phone call. He also explains why he still avoids hiring a COO, how he evaluates executive talent, and why long-term trust is his leadership superpower.
Whether you’re building in AI, navigating founder-operator transitions, or learning to scale without burning out, Craig’s story is packed with hard-earned lessons and honest insights.
Where to find Craig:
Timestamps:
(00:00 ) Starting in door-to-door sales
(02:54 ) What Craig learned about grit from early sales jobs
(04:42 ) From Apple to law school to M&A at Wilson Sonsini
(07:22 ) How Cisco influenced his approach to acquisitions
(08:32 ) The founding of GrandCentral and acquisition by Google
(09:12 ) Leaving Google to build again
(13:22 ) Why Craig couldn’t stay a middle manager
(14:53 ) What Dialpad is and how it started
(17:36 ) Google Ventures’ support and early Dialpad funding
(21:03 ) What startup life looked like in the pool house
(24:17 ) Family trade-offs and how Craig stayed connected
(28:23 ) Acquiring TalkIQ and the AI unlock
(33:37 ) Why Dialpad was years ahead in AI
(35:09 ) Lessons from integrating an early-stage acquisition
(37:43 ) What tech reveals about culture
(39:39 ) How Craig grew from scrappy founder to CEO
(42:20 ) Delegating to operators while staying strategic
(43:30 ) Why hiring executives is so hard
(47:23 ) How he evaluates cultural fit and long-term potential
(49:26 ) Loyalty, longevity, and building a trusted leadership team
(50:57 ) Craig’s moment of truth and the most stressful day of his career
(55:48 ) What he wishes he knew earlier
(57:46 ) His advice for founders in the AI era
In this episode, you’ll learn:
- How to evaluate and integrate an early-stage acquisition
- Why trust and long-term relationships build company resilience
- What most founders get wrong about hiring senior executives
- Why naivete is an advantage in fast-changing markets
- How to stay optimistic in the face of startup volatility
- Why Craig empowers teams with autonomy, not layers
- How a founder mindset helps navigate economic shocks
- What it takes to lead through multiple tech transitions
- How to pick colleagues and partners you can grow with for decades
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