How can you get the most out of your year-end? In this solo episode of Not Another CEO Podcast, David explores how leaders can leverage the end of the year for reflection, rallying their troops, and recharging for what lies ahead.
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #DecemberCEOPulse
Chapters:
00:00 Intro
01:22 Reflect: Assessing Achievements
05:15 Rally: Energizing Your Team
11:14 Recharge: Taking Time to Rest
13:33 Outro
How do you keep building when every month your company is almost out of money, and quitting would be the logical choice?
In this episode, Artem Rodichev shares the gritty, unfiltered story of Ex Human’s near-death year. Instead of shutting the company down, that year hardened the team, shaped the culture, and created a level of resilience that became Ex Human’s defining advantage.
Now Ex Human is profitable and building empathetic AI characters capable of multimodal emotional intelligence, technology designed to see, hear, and feel in ways that help combat loneliness. Artem also discusses his path from leading AI at Replica to building a company that spans both consumer and enterprise markets, powered by millions of user-created AI characters that generate a unique data advantage.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #ExHuman
Chapters:
00:00 Intro
01:24 The Importance of Persistence
04:33 Belief in the Vision
05:53 Personal Sacrifices and Company Culture
11:07 Solo Founder Challenges
12:29 Building a Strong Team
14:45 The Role of a Founder
18:47 Consumer AI and Empathetic Companions
29:41 Breaking Inertia: Leaving a Successful Company
32:06 Limitations and New Opportunities: The Birth of a New Venture
34:50 B2C and B2B: Balancing Two Markets
37:11 The Importance of Data in AI Development
42:28 Challenges and Competitions in the AI Market
49:41 Personal Background: From Kazakhstan to Tech Entrepreneurship
57:00 Final Reflections and Advice for Aspiring Entrepreneurs
58:39 Outro
How do you scale a company from zero to $100 million in 18 months without losing quality, clarity, or control?
In this episode, Matt Price shares the remarkable story of building Crescendo, one of the fastest-growing companies ever featured on the show, by reimagining customer experience through advanced AI and deeply trained specialists. Matt’s journey has come full circle: from a technical support rep early in his career, to scaling Zendesk, to now creating an entirely new model for enterprise-grade customer care.
Matt opens up about assembling an elite leadership team in record time, creating a vertically integrated product-and-operations engine, and designing a culture anchored around accountability, curiosity, and constant communication. He also explains why outcome-based pricing changes everything, how General Catalyst’s creation model gave Crescendo an unfair advantage, and why traditional BPOs simply aren’t positioned for the AI era. This is a masterclass in speed, focus, and operational excellence.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Crescendo
Chapters:
00:00 Intro
01:32 Building a High-Impact Team
03:40 The Role of AI in Customer Service
06:03 Rapid Growth and Company Evolution
07:58 Leadership and Team Dynamics
11:03 AI Integration and Product Development
21:53 Founding Crescendo and Market Opportunities
28:10 Challenges and Focus as a CEO
31:08 The CEO's Influence on Team Dynamics
35:00 Outcome-Based Pricing in SaaS
36:22 Challenges and Benefits of Outcome-Based Models
41:25 Strategic Growth Through Acquisitions
47:04 The Future Vision for Crescendo
48:34 Personal Journey and Early Career
58:33 Advice for Aspiring Entrepreneurs
59:29 Outro
Have you ever wondered what it takes to build a company from your garage to a public entity?
In this episode, Chieh Huang shares the raw, unfiltered story of building Boxed from a garage into a national e-commerce brand serving tens of millions of customers, and the emotional toll, unlikely breakthroughs, and market forces that shaped every chapter of the journey. He reflects on the lonely months of almost no orders, the overnight surge that changed everything, the pressure of becoming a public company CEO, and the reality that even the strongest operators can’t outrun macro cycles.
Chieh also opens up about what happens after the final chapter closes, the exhaustion, the identity shift, and the unexpected necessity of real recovery. His honesty about the highs, lows, and lessons he’s taking into his next company makes this a powerful episode for founders navigating their own versions of the broken-glass analogy.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Boxed
Chapters:
00:00 Intro
00:46 The Journey of Boxed
02:42 The Purpose Behind Boxed
07:14 Starting in the Garage
09:23 The Big Break and Rapid Growth
20:36 Fundraising Challenges and Successes
26:02 Navigating Market Ups and Downs
32:09 Reflecting on Past Experiences
33:59 Journey to Going Public
36:26 Challenges of Being a Public Company CEO
39:22 Navigating Investor Relationships
44:17 Balancing Work and Avoiding Burnout
50:03 The End of Boxed and New Beginnings
55:03 Early Entrepreneurial Spirit
57:54 Role Models and Mentors
01:01:25 Core Motivations and Advice
01:05:51 Outro
When was the last time you paused long enough to thank the people who quietly helped you build?
In this special compilation episode, we highlight moments from eleven CEOs who reflected on the investors that shaped their companies’ trajectories, not just through capital, but through conviction, guidance, and belief. These clips reveal how the right investors help founders stay grounded in their mission, navigate uncertainty, and make better decisions during pivotal moments of growth.
Across these stories, one theme stands out: exceptional investors don’t just finance a business, they help founders become better leaders. They open doors, challenge thinking, and offer support that often goes unspoken and uncelebrated. As we head into the holiday season, this episode is an invitation for CEOs to pause, reflect, and acknowledge the people whose partnership made the climb possible.
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess
Chapters:
00:00 Intro
02:17 Daniel Chait - Greenhouse
02:54 Kyle Porter - Salesloft
06:50 Craig Walker - Dialpad
13:24 Dane Atkinson - Odeko
21:11 Diego Oppenheimer - Algorithmia
24:46 Itamar Friedman - Qodo
28:43 Jeron Paul - Spiff
34:03 Nadia Boujarwah - Dia&Co
38:59 Nick Patrick - Radar
44:16 Toby Kraus - Lightship
53:30 Tom Buiocchi - ServiceChannel
54:09 Outro
How can you motivate your team to embrace AI in their daily work? In this solo episode of Not Another CEO Podcast, David discusses strategies to drive an AI-first mindset in your company.
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #NovemberCEOPulse
Chapters:
00:00 Intro
03:16 Get Your Team Using AI
06:24 Get Traction With Focused AI Projects
10:42 Install A Champion To Own AI
14:00 Outro
How do you build one of the fastest-growing integration platforms in tech, while keeping culture, momentum, and innovation in sync?
In this episode, Shensi Ding, Co-Founder and CEO of Merge, shares her journey from investment banking to leading one of the most successful integration infrastructure companies in the market. She opens up about the company’s evolution, from a small startup in San Francisco to a category leader powering technology products and AI agents for companies like Ramp and OpenAI.
Shensi also discusses how she built Merge’s in-person culture during the height of the pandemic, what it takes to recruit top talent, and the lessons she’s learned about decision-making, adaptability, and sustaining momentum as a founder.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Merge
Chapters:
00:00 Intro
01:40 Starting Merge During the Pandemic
02:50 Challenges of In-Person Work Culture
03:42 Expanding to New York and International Markets
04:50 Maintaining Work Ethic and Decision Making
06:42 Evolving Leadership and Learning from Mistakes
10:56 Bringing Industry Leaders to Inspire the Team
13:56 Acquiring the First Customers
16:38 Dealing with Copycats and Maintaining Quality
21:08 Product Evolution and Adapting to AI
27:59 The Halo Effect of New Products
29:59 Promoting AI Tools Internally
33:15 Fundraising Challenges and Successes
38:08 Moving Upmarket and Adapting
41:42 Founders' Background and Journey
47:16 Balancing Work and Personal Life
50:41 Outro
How do the best founders learn faster, think deeper, and turn that mindset into companies that endure for decades?
In this episode, host David Politis sits down with Nikhil Basu Trivedi, Co-Founder of Footwork, one of Silicon Valley’s most respected early-stage investors. Nikhil’s career spans both sides of the table, from co-founding Artsy, the groundbreaking online art platform, to investing in category-defining companies like Canva, Lattice, Frame.io, and The Farmer’s Dog.
Nikhil shares how he evaluates founders, why the “slope of learning” is the most important quality he looks for, and how he builds long-term partnerships based on trust, curiosity, and shared ambition. He also opens up about the changing venture landscape, the hype and opportunity of AI, and what it means to be an investor who has truly walked in a founder’s shoes.
Quote of the Show:
Links:
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Footwork
Chapters:
00:00 Intro
01:27 Key Traits in Founders: The Slope of Learning
04:59 The Importance of First Impressions in Pitching
13:48 Evaluating and Supporting Portfolio Companies
19:44 The Impact of AI on Venture Capital
24:04 The Value of Thought Partnership
31:10 Reflections on Missed Opportunities and Career Choices
36:30 Future Aspirations for Footwork
38.25 Outro
How do you build something meaningful without losing yourself in the process?
In this episode, David talks with Betsy Fore, Co-Founder and former CEO of Tiny Organics and Founding Partner of Velveteen Ventures. Betsy shares her remarkable journey from toy inventor to serial entrepreneur and impact investor, becoming the first Native American woman to raise a Series A along the way.
She opens up about co-creating Tiny Organics alongside 100 founding families, facing setbacks like her unaired Shark Tank appearance, and learning to redefine success through purpose and presence. Betsy also reflects on the lessons that shaped her new book, Built on Purpose, blending practical entrepreneurship with spiritual grounding and a values-driven approach to leadership.
Now, through her venture fund and nonprofit, Betsy is focused on investing in solutions that uplift communities, children, and the planet, showing that business can be both profitable and deeply purposeful.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #TinyOrganics #VelveteenVentures
Chapters:
00:00 Intro
01:26 Building Tiny Organics with Founding Families
07:47 From Tiny Organics to National Recognition
08:34 Lessons from a Previous Venture
13:51 Shark Tank Experience
19:18 Navigating the Venture Capital Landscape
25:07 Securing Initial Funding and Building a Strong Advisory Board
26:15 Realizing the Importance of Giving Back
27:55 Founding Natives Rising and Healing Through NLP
29:20 Investing in Underrepresented Founders
31:39 Writing 'Built on Purpose' and the Power of Manifestation
35:38 Inspiring Stories from Native American Founders
38:21 Launching a Venture Fund with a Purpose
41:26 From Rural Illinois to International Success
49:35 The Importance of Self-Compassion for Founders
50:35 Outro
How do you scale exceptional customer support without losing the human touch?
In this episode, David sits down with Ryan Wang, Co-Founder and CEO of Assembled, to explore this very challenge. What started as a simple scheduling tool has evolved into an AI-powered customer support platform trusted by leading companies like DoorDash and Salesforce.
Ryan opens up about the realities of scaling a fast-growing company, balancing innovation with culture, leading through learning, and keeping mission and execution at the heart of everything. His insights offer a playbook for founders and leaders aiming to build resilient, adaptable organizations.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Assembled
Chapters:
00:00 Intro
01:22 Deep Dive into Leadership and Management
04:25 Networking with Industry Leaders
09:12 Balancing Multiple Roles as CEO
15:31 Transition to CEO Role
23:33 Evolution of Assembled's Product
29:13 Running Through Y Combinator
30:28 Demo Days and Team Dynamics
32:16 Staying on Top of Rapid Changes
35:53 The Concept of Moat in Business
40:22 Adapting to AI and Cultural Challenges
45:09 Future Vision for Assembled
47:42 Personal Background and Influences
52:45 Advice for Aspiring Entrepreneurs
55:15 Outro
How can founders build companies that scale without burning themselves out in the process?
In this episode, Noah Shanok, Founder and former CEO of Stitcher, reflects on his entrepreneurial journey leading one of the earliest podcast platforms, which ultimately sold to SiriusXM for $325 million. He shares candid lessons from the early days of Stitcher, navigating sleepless nights, hiring versatile early employees, and learning from missteps along the way.
Noah also discusses how his time at Amazon influenced his approach to structured hiring, why prioritizing personal well-being is critical for long-term effectiveness, and how founders can overcome imposter syndrome. Now working as a coach to entrepreneurs, he brings a unique perspective on balancing growth with sustainability, drawing on both successes and challenges from his own journey.
Quote of the Show:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Stitcher
Chapters:
00:00 Intro
01:42 The Importance of Hiring a Versatile Team Member
02:24 Finding the Right Person for the Job
07:00 Lessons from Amazon's Hiring Process
13:29 Stitcher's Early Business Development Deals
21:37 Challenges and Realities of Strategic Partnerships
26:53 Coaching Founders: Common Challenges and Solutions
32:29 Transformative Changes and New Habits
33:13 The Impact of Prioritizing Self-Care
37:50 The Power of CEO Support Systems
38:24 Dealing with Imposter Syndrome
45:24 Lessons from Stitcher: Timing and Market Dynamics
48:58 The Drive to Build and Help Others
51:50 The Importance of Mentors and Advisors
57:25 The Need for a Support System for CEOs
59:38 Advice for Founders
1:00:58 Outro
Do you know how essential a support system is for a CEO? In this solo episode of Not Another CEO Podcast, David discusses the often overlooked, yet critical support necessary for CEO success.
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #OctoberCEOPulse
Chapters:
00:00 Intro
02:53 The Importance of a CEO Support System
03:57 Key Components of a CEO Support System
05:10 The Role of Co-Founders and Key Executives
07:33 The Value of Executive Assistants and Chiefs of Staff
09:24 Leveraging Board Members and Advisors
14:38 The Importance of Therapists and Personal Relationships
19:16 The Power of CEO Peer Networks
21:27 Outro
What can founders learn from an entrepreneur who has built, scaled, and exited multiple companies while reshaping an entire city’s startup ecosystem?
In this episode, David Cummings, Founder and CEO of Atlanta Ventures, reflects on his journey building ten companies, including Pardot, which sold to ExactTarget for $95 million, and investing in some of Atlanta’s most successful startups like Calendly and SalesLoft. He shares the guiding principles that shaped his entrepreneurial path, from building a culture-first company to navigating the realities of bootstrapping, scaling, and liquidity events.
David also opens up about his role in transforming Atlanta’s tech landscape through Atlanta Tech Village and his ambitious project to redevelop South Downtown into a vibrant startup district. Along the way, he offers candid advice for founders on leadership, resilience, and blending work with life in a sustainable way.
Quote of the Show:
Links:
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #AtlantaVentures
Chapters:
00:00 Intro
01:44 Early Challenges and Successes at Pardot
02:24 Building a Strong Company Culture
03:02 Product Vision and Customer Focus
05:55 Transition from Doer to Leader
12:49 Bootstrapping vs. Fundraising
20:34 The ExactTarget Acquisition
31:08 Reflections on Entrepreneurship and Liquidity
36:52 Understanding Startup Valuations
38:09 Building a Winning Team at Pardot
41:17 Investing in Founders with the Right Attributes
43:29 The Atlanta Tech Village Journey
51:44 Revitalizing Downtown Atlanta
01:00:56 David's Entrepreneurial Beginnings
01:06:57 Balancing Entrepreneurship and Family
01:10:36 Advice for Aspiring Entrepreneurs
01:12:50 Outro
THE FIRST EPISODE OF INVESTORS UNFILTERED!
What do venture capitalists really look for in founders, and how can CEOs build strong, lasting relationships with their investors? In this episode, Chip Hazard, Co-Founder and General Partner at Flybridge, offers an inside look at how VCs think about evaluating founders, funding opportunities, and long-term partnerships. He shares the traits that consistently stand out and explains how these factors matter as much as business metrics, especially in the early stages.
Chip also unpacks the evolution of fundraising, from vision-driven early rounds to later stages where metrics and revenue quality become critical. He reflects on the dynamics of board relationships, the importance of clear alignment on strategy, and why constructive feedback and ongoing communication are vital to scaling effectively.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Flybridge
Chapters:
00:00 Intro
02:11 The Key Traits of Successful Founders
04:09 Assessing Founders Beyond the Pitch
06:04 Stages of Investment and What VCs Look For
15:36 Working with Founders Post-Investment
22:08 The Importance of External Perspectives
25:52 Challenges in Board Dynamics
30:37 Aligning with Venture Capitalists
37:55 Geographical Differences in Startups
40:13 Reflections and Regrets in Venture Capital
43:18 The Passion for Investing
45:47 Outro
What does it take to reinvent an entire industry that’s been rooted in tradition for decades? In this episode, Michael Jacobson, CEO of French Florist, shares his journey from corporate consulting to transforming the floral business.
Michael explains how he grew a single 3,000-square-foot location into a $9 million operation by modernizing systems, cutting inefficiencies from the supply chain, and infusing emotion into every part of the customer experience. He also reflects on the challenges of scaling in a traditional industry, the decision to franchise, and the importance of mentorship, high standards, and culture in building a business that lasts.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #FrenchFlorist
Chapters:
00:00 Intro
01:38 Transformative Leadership and Infusing Emotion
03:22 Building a Culture of Love and Excellence
08:25 Hiring for Values and Unconventional Interviews
14:51 The Origin Story of French Florist
19:19 Initial Challenges and Early Improvements
24:36 Revolutionizing the Floral Industry with Technology
31:43 Revenue Growth and Optimization
33:15 Supply Chain Innovations
35:15 Direct Importing from Farms
37:36 Challenges in the Floral Industry
40:28 Franchising and Expansion
48:18 Personal Reflections and Motivation
1:01:01 Outro
How can CEOs stay adaptable while leading through pivots, growth, and constant change? In this episode, Scott Voigt, Founder and CEO of Fullstory, shares his journey from a failed first product to creating the leading digital analytics platform used by thousands of companies worldwide.
Scott dives into the tough realities of leadership, from making difficult people decisions to evolving as a CEO as the company scales. He opens up about the power of storytelling in fundraising and leadership, the importance of mental well-being, and the lessons he’s learned from being an early builder in Atlanta’s thriving tech ecosystem.
Takeaways:
Quote of the Show:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Fullstory
Chapters:
00:00 Intro
01:36 The Biggest Impactful Decision at Fullstory
03:35 The Challenges and Lessons of Letting People Go
08:38 Hiring Philosophy and Interview Techniques
18:56 The Importance of Storytelling as a CEO
24:54 Fundraising Journey and Product Pivot
33:38 Reflecting on the Early Struggles
37:14 The Importance of Team Chemistry
43:28 Navigating the Atlanta Tech Scene
48:20 Biggest Challenges and Lessons Learned
51:01 Future Vision for Fullstory
57:15 Personal Reflections and Advice
01:07:53 Outro
How do you scale a global company while transforming an industry as traditional as law?
In this episode, Max Junestrand, Co-Founder and CEO of Legora, shares how he’s building the world’s first truly collaborative AI platform for legal services.
Max reflects on his unconventional path from engineer to entrepreneur, what it took to win over law firms as an outsider, and why ambition and adaptability matter more than experience in fast-scaling environments. He also opens up about navigating hypergrowth, hiring with intention, and the cultural values that drive Legora’s mission to reshape how legal work gets done.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Legora
Chapters:
00:00 Intro
01:41 Founding and Early Challenges
02:42 Sales Strategy and Growth
06:40 Building a Strong Team
13:55 Global Expansion
29:43 Expanding Beyond Local Markets
31:13 Challenges of Going Global
33:40 Product Development and Iteration
37:08 Competing with Industry Giants
42:43 YC Experience and Early Challenges
49:52 Personal Background and Motivation
1:00:48 Outro
Ever wondered what to consider when hiring your first key employees beyond the founding team? Or what are the secrets to successful fundraising for startups? In this solo episode of Not Another CEO Podcast, David shares his insights from CEO gatherings, trends he’s noticed in the community, and a recent family trip that emphasizes the importance of origin stories.
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #AugustCEOPulse
Chapters:
00:00 Intro
02:55 Hiring Your Founding EA
13:08 Fundraising Isn’t Fair
18:55 The Importance of Origin Stories
23:55 Outro
What does it take to build and scale a company while staying grounded in your values? In this episode, Flint Lane reflects on his journey founding and growing Billtrust and coming out of retirement to start Major League Table Tennis. He shares lessons on resilience, leadership, and the balance between personal integrity and business success.
Flint also discusses the challenges of navigating growth, what he has learned about himself along the way, and the importance of staying true to purpose even in difficult times.
Takeaways:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #MajorLeagueTableTennis
Chapters:
00:00 Intro
01:23 Flint Lane's New Venture: Major League Table Tennis
01:56 The Importance of Stacking Wins
04:06 Effective Communication and Decision Making
06:30 The Role of Transparency in Leadership
14:51 Hiring the Right People
21:06 The Evolution of Executive Teams
27:17 The Importance of a Strong Board
31:53 Navigating the Startup Journey
33:19 The Decision to Go Public
36:34 The Acquisition Process
39:06 Cybersecurity Crisis
43:54 Transition to Major League Table Tennis
49:33 Reflections on Entrepreneurship
56:46 Final Thoughts and Advice
57:48 Outro
How does an aspiring product leader transition to the helm of a successful tech company? In this episode, Nick Patrick shares his unique perspective on leadership and growth in the tech industry.
Nick discusses critical insights on how Radar's unique product strategy, company culture, and operational practices have driven their success.
Takeaways:
Quote of the Show:
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Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Radar
Chapters:
00:00 Intro
01:12 The Impact of Multi-Product Strategy
03:16 Challenges and Management of Multi-Product Approach
07:43 Product Involvement and Team Structure
12:30 Customer-Centric Engineering
14:42 In-Person Collaboration and Office Culture
19:52 Founding Radar and Early Challenges
28:36 Fundraising Journey and Investor Relations
34:55 Navigating Business Through Uncertain Times
35:47 Adapting to Market Changes and Setting Expectations
38:20 Cultural Shifts and Social Issues
41:21 Future Vision for Radar
43:24 Personal Journey and Entrepreneurial Spirit
47:38 Balancing Work and Family Life
51:03 Advice for Aspiring Entrepreneurs
54:25 Outro