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

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

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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

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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

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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/

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Follow Alisa Cohn on

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

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Bob Young co-founded Red Hat, the first company to build a successful business around open source software, and helped shape the modern internet in the process. In this episode, Bob shares the story of how Red Hat went from a CD in a Ziploc bag to a billion-dollar business that inspired GitHub, Coinbase, and much of the cloud infrastructure we use today.

But this conversation is about more than just software. Bob opens up about betting his family’s finances on Red Hat, the moment he realized he wasn’t meant to be a public company CEO, and why he believes capitalism, when done right, can be a powerful force for good.

He also shares what he's building now (including a needlepoint company), how he thinks about failure, and the one principle he thinks every founder should live by.

Where to find Bob:

Lulu.com

Needlepoint.com

Timestamps:

(00:00) The challenge of fragmented attention and overbooked schedules

(05:09) Red Hat’s founding story and the philosophy behind open source

(08:56) Why the internet is the world’s largest open source project

(13:34) From newsletter publishing to reinventing Linux

(19:49) Why customers chose Red Hat: control, not cost

(22:12) The business model insight that changed everything

(24:44) How IBM’s services model inspired Red Hat’s structure

(27:36) Scaling Linux for enterprise and dealing with constant updates

(36:24) Proprietary software as a modern feudal system

(43:33) Racking up $50K in credit card debt to keep Red Hat alive

(49:01) Trust, marriage, and startup risk

(55:05) Leaving Red Hat and why Bob stepped down as CEO

(59:23) What sleep taught Bob about optimism and recovery

(01:06:10) Red Hat’s culture of ownership and accountability

(01:14:24) Why Bob still builds: making the world a better place through business

(01:15:02) The importance of discipline and organization

(01:17:08) Founders’ advice: serve customer needs, not just wants

In this episode, you’ll learn:

• How Red Hat became the first successful open source company
• Why control—not price—is the real value of open source software
• What makes transparency a business strategy, not just a virtue
• How capitalism and idealism can actually align
• Why understanding customer needs matters more than their wants
• The difference between proprietary and democratic tech systems
• How to build culture that owns mistakes and learns out loud
• What it really means to commit to your co-founder and spouse
• How to navigate failure, burnout, and your own limitations as a leader
• What keeps Bob starting new companies in his third and fourth acts

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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)

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Jonathan Wolf is the co-founder and CEO of ZOE, the science-based nutrition company using data to transform how people eat. In this candid conversation, he joins Alisa to explore what it takes to build a mission-driven company, how to lead with more clarity and transparency, and why the way we eat is more broken and more fixable than most people think.

ZOE’s origin story is as unconventional as it is inspiring. After scaling Critéo into a billion-dollar business, Jonathan stepped away with no plan and plenty of questions. That wandering period led him to microbiome researcher Tim Spector, and from there, to the bold idea of using AI and big data to personalize nutrition at scale. Eight years and 250,000 microbiome samples later, ZOE is running the world’s largest nutrition science study and has launched a free app to help people assess their food in real time.

In this episode:

• Why Jonathan left the world of adtech in search of purpose
• His sabbatical was a challenging period of self-discovery.
• The importance of relationships over ideas became clear to him.
• How he navigated the founder’s journey
• The scientific gaps in mainstream nutrition advice
• What most people misunderstand about ultra-processed food
• How ZOE turned a research project into a product that helps millions
• What coffee can reveal about your gut microbiome
• Why leadership gets easier when you stop trying to be liked
• How Jonathan uses one key question to make sure he’s actually being heard
• Why ZOE launched a free tool to put science into people’s hands
• How to communicate clearly as a CEO without over-explaining
• Why repeating your message 100 times is part of the job
• How to hire people who care more about the mission than the resume
• What coaching and therapy taught Jonathan about being an effective leader
• Why ZOE’s shift to a free app was a strategic business decision
• How to scale without losing sight of your company’s purpose

Jonathan also shares the emotional and psychological journey of leadership: learning to make hard calls without sugarcoating, building teams that stick, and staying grounded while leading a fast-growing company.

ZOE’s new free app is now available in the US. It uses AI to analyze any food item or meal for its processing risk and nutritional quality, helping people make smarter choices instantly. If you care about your energy, mood, and long-term health, this episode will change how you think about food and leadership.

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• 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)

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Kass and Mike Lazerow are serial entrepreneurs, seasoned investors, and co-authors of the upcoming book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success. They join Alisa to share an unfiltered look at what it really takes to build companies, navigate chaos, and stay married through it all.

Known for founding Golf.com and Buddy Media, which they sold to Salesforce for $745 million, Kass and Mike have also backed more than 100 early-stage startups. Their portfolio includes Scopely, acquired for $5 billion, and Liquid Death. In this conversation, they recount the wild highs and lows of startup life, from raising three kids while raising capital to walking away from a higher offer because it came with too much risk.

You’ll hear about:

• The dot-com crash that nearly killed Golf.com and how they raised money to buy it back from bankruptcy
  
  
• The early bet they placed on Facebook that became Buddy Media
  
  
• Why did they choose Salesforce over a larger offer from Google
  
  
• How they built a radically transparent culture that kept employees during a 3-month no-pay period
  
  
• What it's really like to sell a company for hundreds of millions, then stay on as an employee
  
  
• How ego, secrecy, and shiny-object syndrome kill founders
  
  
• What it takes to choose the right co-founder and build a business that lasts
  
  

They also share what it's like to run companies as a married couple, including how they divide responsibilities, handle stress, and maintain date nights through multiple exits and pivots.

Also in this episode:

• The story behind Mike’s near-death health crisis and how it changed his entire mindset
  
  
• Why Kass believes in minivans and Mike believes in showing up for everything
  
  
• The advice they give to every founder they backed
  
  
• How their kids learned more from watching than listening
  
  

Their new book, Shoveling Sh!t, hits shelves on June 3, 2025. It captures 50 hard-earned lessons that can help any founder become a better leader and build a life that actually works.

About Kass & Mike:
Kass and Mike Lazerow are entrepreneurs and investors best known for building and selling Buddy Media, a leading social media marketing platform, to Salesforce for $745 million. They co-founded Golf.com early in their careers and have since supported more than 100 startups as investors and advisors. Notable investments include Scopely and Liquid Death. They are also sought-after speakers, writers, and podcast guests. Their book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success is out June 3, 2025.

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)

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David Ko is the CEO and board member of Calm, the #1 app for sleep, meditation, and mindfulness. A former healthcare executive and tech operator, David previously served as COO of Zynga, held senior roles at Yahoo!, and founded a healthtech company acquired by Calm. He is the bestselling author of Recharge, and has been recognized by TIME, LinkedIn, RockHealth, and NYU Stern for his leadership in digital health.

What you’ll learn:

• How David transitioned from gaming to healthcare through mission-driven insight
• The real story behind Calm’s evolution from sleep and meditation to global mental health
• Why David uses “battery level” as a tool for checking in at work
• How leaders can model vulnerability without sacrificing authority
• Why burnout stems from poor workload management, not just long hours
• The power of shared purpose in turbulent times
• How Calm uses rituals like Jay Shetty meditations and Zoom-free days to reinforce its culture
• Why sleep, diet, and presence are core to David’s leadership performance
• How transparency builds trust even when the news isn’t good
• Why the conversation around mental health needs to start at the top

Some takeaways:

➡️ Stress is not the problem. Unchecked, unacknowledged stress is. Good stress can fuel resilience and performance.
➡️ “How’s your battery?” is a more meaningful check-in than “How are you?”
➡️ Burnout often comes from lack of clarity and excessive task stacking, not too many hours.
➡️ Leaders must explain the why behind priorities and remove as much as they assign.
➡️ Transparency about culture survey results builds psychological safety.
➡️ Rituals like 90-second meditations help reset and re-center teams.
➡️ Leadership can be lonely. Trusted colleagues make a critical difference.
➡️ Presence matters more than hours. Back-to-back meetings are not a badge of honor.
➡️ Sharing your own mental health journey is not weakness. It’s how resilient teams are built.
➡️ “We take better care of our phone batteries than our mental health batteries.” Time to change that.

Where to find David Ko:

• LinkedIn: https://www.linkedin.com/in/daveko/
• Calm: https://www.calm.com
• Book: Recharge: Boosting Your Mental Battery One Conversation at a Time
• Podcast: Recharge (available on major platforms)

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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

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Mike Seckler is a two-time entrepreneur and tech startup founder who led a company through the dot-com boom and bust, and now leads the charge as CEO of Justworks, the HR tech company focused on uplifting small businesses. In this conversation, he shares hard-earned lessons from building one of the earliest SaaS HR startups, navigating turbulent markets, and guiding Justworks through major transitions. We dive into founder resilience, building high-functioning boards, scaling culture in a hybrid world, and why mission-driven support for small businesses matters now more than ever.

What You’ll Learn:

• How Mike evolved from first-time founder to CEO of Justworks
• The “self-inflicted wound quotient” every founder faces—and how to reduce it
• How values shape Justworks’ culture and decision-making
• The impact of structured, intentional board leadership
• Why Justworks pulled its IPO and why it was the right call
• Lessons from integrating a remote team post-acquisition
• How to stay adaptable without losing momentum
• Why stepping back (even for vacation) makes you a stronger leader
• Balancing in-person U.S. operations with global remote teams
• The importance of staying close to your end user
  
  

Key Takeaways:

➡️ Minimize your “self-inflicted wounds”: Founders often make early decisions—co-founder choices, board composition, capital structure—that can hinder growth. Mike calls this your “self-inflicted wound quotient.” Keep it low.

➡️ Good governance starts with leadership: Don’t wait for your board to self-organize. Set norms, prep materials early, and lead it the way you’d lead your exec team.

➡️ Clarity beats comfort: From acquisitions to layoffs, Mike emphasizes over-communicating the why and making decisions that would “look good on the front page of the Wall Street Journal.”

➡️ Culture isn’t what you say—it’s what you do: Values like “comradery” and “grit” must be defined through behavior and reinforced through recognition, awards, and storytelling.

➡️ Board building is strategic: Justworks’ board includes domain-specific experts—from healthcare to global payments. Choose members like you’d build your C-suite.

➡️ Hard decisions made early pay off later: Fix the roof when it’s sunny. The cost of delay is always higher.

➡️ Remote vs. in-person is not either/or: Justworks combines in-office culture in the U.S. with distributed international teams, intentionally designing for both.

➡️ Real leadership means managing your energy: Mike learned from parenting that being the calmest person in the room is often your superpower.

➡️ Mission attracts the right people: Employees at Justworks are deeply motivated by its purpose—to serve small businesses as heroes of the economy.

Where to find Mike Seckler:

• LinkedIn
• Justworks
  
  

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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