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:

• 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

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

Connect with Alisa!

Follow Alisa Cohn on

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Brad Feld has spent over 40 years building companies, mentoring founders, and investing in the startup ecosystem. He’s the co-founder of Techstars, a prolific venture capitalist, and the author of nine books.

In this episode, Brad opens up about the mental reset that came with turning 60, why he stopped chasing “more,” and what led him to dust off a book draft about mentorship that had been sitting on the shelf. We go deep into his new book Give First, his belief in non-transactional generosity, and why he thinks founders should lead from curiosity, not ego.

Brad also shares what went wrong at Techstars, what it taught him about founder empathy, and how he thinks about legacy in a world where everything is temporary.

Where to find Brad:

• feld.com
• Give First (book)

Timestamps:
(00:00) Why Brad chose to go into hibernation
(03:36) How stepping back gave him a 9-to-5 for the first time
(06:58) Returning to code and reading 3 books a week
(08:05) The four things Brad actually loves
(10:11) Not striving, not optimizing: a new mindset for a new decade
(13:14) The messy journey of writing Give First
(15:08) Feedback that reshaped the book
(17:34) Techstars’ awkward teenage years
(19:59) Coming out of hibernation, temporarily
(23:32) Alter egos: Brad the Book Salesman, Vlad, and Spike
(29:14) The pain of watching Techstars struggle publicly
(34:30) How founder empathy deepened after Techstars’ turbulence
(36:28) What Give First really means and what it does not
(38:49) Positive-sum, multi-turn thinking
(41:34) Why tennis is the perfect metaphor for long-term success
(45:00) Give First as the startup community engine
(48:21) Mentorship without expectations
(50:07) Socratic questioning and the five whys
(54:00) Diagnosing startup fundraising problems
(56:32) Being open to randomness
(58:57) The power of short assignments and low-stakes access
(01:04:28) Why Brad keeps writing: to learn
(01:07:14) What he wishes he knew earlier
(01:10:34) Advice for founders stepping into leadership
(01:12:38) Mortality, meaning, and option value

In this episode, you’ll learn:

• How Give First evolved from a Techstars mantra into a movement
• The difference between mentorship and advice
• Why and how being a giver pays off
• How to set boundaries while still being responsive
• What makes founder relationships thrive or break
• Why being open to randomness can change everything
• How to navigate difficult company phases with empathy
• What Brad believes really matters in the third act of life

Connect with Alisa!

Follow Alisa Cohn on

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

David is the creator of Ruby on Rails, Co-Owner of 37signals, best-selling author, Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man.

He writes regularly on HEY World and speaks on The REWORK Podcast.

Hundreds of thousands of programmers around the world have built amazing applications using Ruby on Rails, an open-source web framework he created in 2003, and continues to develop to this day. Some of the more famous include Github, Shopify, Airbnb, Square, Coinbase, and Zendesk.

For my newest episode of From Start-Up to Grown-Up, I talk with David Heinemeier Hansson, Co-Founder of 37signals, to explore his journey of innovation, remote work, and unconventional management.

Learn more about DHH | Website
https://dhh.dk/

Connect with Alisa!

Follow Alisa Cohn on

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon