#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

2025-08-11

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 b...

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:

Dialpad
LinkedIn

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