Not Another CEO Podcast

Not Another CEO
Not Another CEO Podcast

Our mission is to bend the curve for Founders and CEOs. At Not Another CEO, we know there’s no formula for running a business. Leadership is forged through unique journeys, real challenges, and hard lessons. Our exclusive content showcases unfiltered stories and practical guidance from those who’ve crawled through the trenches. Our platform offers the largest library of CEO insights and how-to guides, sourced directly from a diverse community of leaders. Find our full video library, detailed playbooks, deep dives, and lessons learned on our Substack here ➡️ https://notanotherceo.substack.com/

  1. Building, Leading, and Paying It Forward - Ellen Rubin - Causely - Episode #53

    3D AGO

    Building, Leading, and Paying It Forward - Ellen Rubin - Causely - Episode #53

    What can you learn from someone who built and sold multiple enterprise startups, led teams through acquisitions, and now mentors the next generation of Founders? In this episode, Ellen Rubin shares lessons from her journey as a serial Founder and now Operating Partner at Glasswing Ventures.  She talks about building strong cultures, nurturing early career talent, supporting women in tech, and helping startups avoid hype in favor of real-world value. From lunch-and-learns to boardroom decisions, Ellen reflects on what it takes to grow people and companies with clarity and purpose.   Takeaways: How to Spot Future Founders Inside Your Company: By encouraging curiosity and inviting team members into strategic conversations, Ellen helped cultivate talent that would eventually become leaders. She looked for people who asked questions, engaged outside their lane, and showed deep interest in how the business works.Practical Support for Women in Tech: Ellen shares her multi-layered approach to supporting women in technology. She has a personal policy of responding to every outreach from a woman Founder or aspiring leader, offering both encouragement and actionable help.Building Strong Local Ecosystems: As a passionate advocate for Boston’s tech scene, Ellen emphasizes the importance of keeping post-exit Founders and big companies engaged with the next generation. She believes physical proximity and local mentorship still matter, even in a hybrid work world.The Value of Regular All-Hands and Real Transparency: At her startups, Ellen hosted weekly all-hands to build alignment and trust. She prioritized consistent updates, company-wide visibility into fundraising stages, and direct Q&A with leadership to keep teams connected and focused.Lessons from Amazon and the PR/FAQ Method: Ellen talks about her time at Amazon and how the press release and FAQ approach to product planning shaped her thinking. She encourages Founders to use writing and storytelling as a way to clarify product vision before building anything.AI That Solves Real Problems: Now an Operating Partner at Glasswing Ventures, Ellen focuses on “intelligent verticals” that use AI to automate industry-specific workflows. She emphasizes the importance of AI being integral to the product, not just a wrapper for marketing. Quote of the Show: "Why wouldn't you wanna be the Founder CEO? That's like the coolest thing in the whole world." - Ellen Rubin Links: LinkedIn: https://www.linkedin.com/in/ellenrubin/Website: https://glasswing.vc/ Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #Causely Chapters: 00:00 Intro 01:45 Key to Startup Success: Building the Right Team 03:08 Exposing Team Members to the Bigger Picture 06:08 Encouraging Curiosity and Engagement 09:45 Supporting Women in Technology 15:03 Challenges in the Tech Industry 17:50 The Boston Tech Ecosystem 21:37 Importance of Local Community in Remote Work Era 27:08 Customer Engagement and Feedback 30:07 Effective Operating Rhythms 35:23 Lessons from Amazon 37:50 Navigating the M&A Process 38:31 Deciding the Right Time to Sell 40:59 Taking Calls from Corporate Development 44:30 The AI Revolution: A 70-Year Overnight Sensation 46:00 The Role of AI in Modern Enterprises 01:01:58 The Importance of Mentorship 01:06:25 Balancing Entrepreneurship and Family 01:09:13 Advice for Aspiring Entrepreneurs 1:10:27 Outro

    1h 12m
  2. Revolutionizing Legal Services - Todd Richheimer - Lawfty - Episode #52

    JUL 8

    Revolutionizing Legal Services - Todd Richheimer - Lawfty - Episode #52

    What happens when you try to fund and scale a legal tech company in one of the most rigidly regulated industries in the country? In this episode, Todd Richheimer shares how he grew Lawfty into a tech-powered personal injury platform that has generated over 55,000 cases and nearly a billion dollars in recoveries. From taking his first client calls on his cell phone to surviving a last-minute funding failure, Todd speaks openly about scaling, leadership evolution, and what the legal world looks like as regulation and AI collide.   Takeaways: Finding the Right Co-Founder in the Hamptons: Todd met his Co-Founder, a former MIT engineer, in the Hamptons. They spent a year working on ideas every Saturday before launching Lawfty, combining Todd’s legal background with Mike’s technical skills.Building with Complementary Strengths: Todd surrounded himself with people who could help him see around corners. He emphasizes that knowing your weaknesses and recruiting to fill them is the most impactful thing he's done as a Founder.The Power of Shameless Outreach: Todd started the company by emailing every contact in his Gmail account. With no product and no revenue, he relied on personal relationships and a willingness to ask for help to land early clients and supporters.Leading with Empathy and Integrity: Todd acknowledges his struggle with letting underperforming team members go, especially when they're good people. Instead of defaulting to layoffs, he focuses on reshuffling and preserving relationships where possible.From Answering Phones to Scaling Teams: For over a year, Todd personally fielded every intake call. That hands-on experience shaped how he hires and builds processes today, and made him intimately familiar with every part of the business.Navigating Capital Constraints Without Venture Money: Due to legal restrictions, Lawfty couldn’t raise institutional equity. Todd had to get creative with structured finance, high-interest loans from individuals, and careful debt planning to scale the company.Legal Tech’s Big Bang Moment: Todd sees the convergence of AI and regulatory change as a generational opportunity for the legal industry. With non-lawyers now allowed to own law firms in more jurisdictions, he believes the space is finally ripe for innovation and scale. Quote of the Show: "Standing up for individuals always felt right to me… so I didn’t necessarily care about the personal view that people had." - Todd Richheimer Links: LinkedIn: https://www.linkedin.com/in/todd-richheimer-esq/Website: https://www.lawfty.com/ Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #Lawfty Chapters: 00:00 Intro 01:41 The Importance of Complementary Skill Sets 02:41 Finding a Co-Founder in an Unlikely Place 03:44 Building Lawfty: From Idea to Execution 06:19 Challenges and Strategies in Team Building 09:29 Navigating the Interview Process 12:47 Understanding Lawfty’s Business Model 16:26 Early Customer Acquisition Tactics 20:57 Fundraising Journey and Lessons Learned 26:38 Scaling as a CEO 29:31 The Legal Tech Revolution 32:09 Challenges in Legal Services 34:52 Building a Tech-Enabled Law Firm 37:14 Overcoming Industry Stigma 42:35 Fundraising Challenges and Solutions 47:01 Personal Journey and Entrepreneurial Drive 54:12 Advice for Aspiring Entrepreneurs 56:48 Outro

    58 min
  3. Relentless Incrementalism - Michael Nyenhuis - UNICEF USA - Episode #51

    JUL 1

    Relentless Incrementalism - Michael Nyenhuis - UNICEF USA - Episode #51

    What does it take to lead a global humanitarian organization through a pandemic and beyond? In this episode, Michael Nyenhuis shares how he has led UNICEF USA since March 2020, starting his role just two weeks after COVID shutdowns began.  Michael talks about building strong boards and leadership teams, the balance between confidence and humility, and how to create connection in a hybrid work world. With decades of experience in humanitarian leadership, he reflects on his journey from journalist to President & CEO, and how staying close to mission and people shapes lasting impact. Find Michael's Newsletter here: https://www.linkedin.com/newsletters/relentless-6990692731056488449/   Takeaways: Rebuilding the Board and Leadership Team: Michael explains how reshaping governance and leadership early in his tenure has been crucial to the success of every organization he has led. He emphasizes getting the right people in place who share the mission and bring diverse skills and chemistry to the table.Evolution Over Revolution: Describing his leadership approach, Michael shares his belief in "relentless incrementalism." He believes consistent, thoughtful progress is more sustainable than sweeping change and that small steps taken regularly are key to building lasting impact.Starting a CEO Role in a Global Pandemic: Michael began his job just as COVID shut the world down. He relied on daily video updates, creative communication, and a golden retriever named Izzy to build relationships remotely. He reflects on the benefits and drawbacks of trying to lead without in-person interaction.Creating Culture in a Hybrid Workplace: UNICEF USA has embraced hybrid work, but Michael is intentional about maintaining connection. From monthly staff engagement days to leadership meetings and all-staff retreats, he builds structured moments for human interaction and relationship-building.Honest Career Advice for Aspiring Humanitarians: Michael stresses that global development is a profession, not just a passion. He shares how expertise, formal experience, and training are key to entering the nonprofit space and why it is important to respect the rigor of humanitarian work.CEO Roundtables and Mentorship by Listening: Michael hosts monthly roundtables with staff based on anniversary dates, offering space for Q&A and storytelling. He also invited youth leaders to mentor him, flipping the script to show respect and learn from the next generation of changemakers.Balancing Confidence and Humility: Michael reflects on the need to balance strong leadership with the humility to listen. Early in his career, he sometimes over-relied on consensus. Today, he sees the value in trusting instincts while remaining open. Quote of the Show: "When you find what you're supposed to do, doors start opening." - Michael Nyenhuis Links: LinkedIn: https://www.linkedin.com/in/michaelnyenhuis/Website: https://www.unicefusa.org/ Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #UNICEFUSA Chapters: 00:00 Intro 01:28 Key Achievements at UNICEF USA 03:18 Building Effective Leadership Teams 14:13 Navigating Challenges During the Pandemic 20:14 Remote and Hybrid Work Dynamics 29:31 CEO Round Table and Onboarding 30:48 Operating Rhythm and Annual Planning 32:18 Monthly Staff Meetings and Engagement 36:22 Public Speaking and Media Training 39:55 Managing Diverse Constituents 42:36 Biggest Challenge: Leading Through COVID-19 45:16 Career Journey and Journalism Background 51:47 Mentorship and Youth Engagement 54:32 Balancing Confidence and Humility in Leadership 58:03 Outro

    59 min
  4. Navigating Early Pivots - Adam Dell - Domain Money - Episode #50

    JUN 24

    Navigating Early Pivots - Adam Dell - Domain Money - Episode #50

    What does it take to walk away from a big idea and start over inside the same company? In this episode of Not Another CEO Podcast, Adam Dell opens up about the journey behind Domain Money.  A serial Founder with multiple exits, Adam reflects on making hard pivots, recruiting top talent personally, navigating investor psychology, and why execution, not ego, is what earns the right to exist. He also shares how AI is transforming financial services and why the emotional highs and lows of startup life never really go away.   Takeaways: Recruiting Personally, Relentlessly: Adam still personally recruits on LinkedIn, often spending hours each day identifying talent, crafting outreach, and filtering for startup fit. He believes CEO-led recruiting cuts through noise and shows prospects the role's importance.A Pivot Before the Crash: Originally conceived as a crypto banking platform, Domain Money pivoted early. Adam made the call based on market fundamentals and moved decisively, even when his team was still optimistic about the original vision.Transparent, Yet Optimistic Leadership: During the pivot, Adam prioritized honesty with his team while maintaining belief in the mission. He communicated openly about uncertainty and made clear that success was entirely on them.Investor Support Built on Track Record and Clarity: Adam credits his investor relationships and clear, data-backed thinking for enabling a smooth pivot. Though they challenged him, his investors supported the shift and recognized the market opportunity in personal finance.AI as a Backbone, Not a Gimmick: AI plays a major role in Domain Money’s operations, especially in improving planning efficiency. Adam is enthusiastic about AI’s pace and scope of change, calling it central to his product vision.The Mental Game of Being a Founder: The pivot at Domain Money required layoffs and letting go of certainty. Adam talks candidly about staying objective under pressure, fighting through doubt, and surrounding himself with trusted mentors while still waking up every day to earn it. Quote of the Show: "That uncertainty, that thing inside of you that forces you to figure it out, is very motivating to me and I quite enjoy it." - Adam Dell Links: LinkedIn: https://www.linkedin.com/in/adamdell/Website: https://www.domainmoney.com/ Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #DomainMoney Chapters: 00:00 Intro 01:25 Recruiting Strategies for Startups 07:15 Fundraising Insights and Market Sentiment 11:46 The Evolution of Domain Money 16:25 Navigating Pivots and Team Buy-In 23:07 Growth Strategies and Partnerships 26:20 Acquisitions and Exits 29:23 Strategic Partnerships and Revenue Growth 30:37 The Impact of AI on Technology and Business 35:12 AI in Financial Planning and Wealth Management 39:51 Challenges and Pivots in Business 49:09 Personal Background and Entrepreneurial Journey 57:37 Advice for Aspiring Entrepreneurs 01:00:30 Outro

    1h 1m
  5. Shoveling $H!T - Kass & Mike Lazerow - Buddy Media - Episode #49

    JUN 17

    Shoveling $H!T - Kass & Mike Lazerow - Buddy Media - Episode #49

    What’s it really like to build a billion-dollar business with your spouse, and live to tell the story? In this special live episode, David Politis sits down with Kass and Mike Lazerow, Co-Founders of Buddy Media and authors of Shoveling $H!T: A Love Story About an Entrepreneur’s Messy Path to Success.. They open up about building cult-like culture, radical transparency, co-founder dynamics, fundraising strategies, pivots, parenting, and everything in between. With humor and honesty, the Lazerows share the unvarnished truth of what it takes to build something meaningful, and survive the chaos along the way.   Takeaways: Building a Cult-like Culture with Intentionality: Kass shares how she focused on creating a high-trust, high-engagement company culture through rituals, transparency, shared values, and even handwritten birthday cards. The foundation was purpose-driven work, and a lot of cupcakes.Radical Focus as a Leadership Imperative: Mike emphasizes the importance of choosing just 3–5 core priorities each quarter and communicating them relentlessly. He admits that his natural state is distraction, and that focus, both personal and organizational, is what drives growth.Fundraising Is a Relationship Business: Mike describes how he built trust with investors over time by sending updates, even to people who said no, and treating everyone with respect, from analysts to GPs. He reframes fundraising as offering a great opportunity, not asking for a favor.The Power (and Pain) of Pivoting: The Lazerows recount the early missteps at Buddy Media, from virtual currency to raffles, before landing on a scalable SaaS product. They stress the importance of cutting old lines of business fast and committing fully to what’s next.Marriage and Co-Founding: They describe co-founding as an intense version of marriage, with shared values, relentless communication, and radical honesty. Kass encourages couples to embrace their lanes and support each other’s growth, both professionally and personally.Startups and Parenting Don’t Balance, But They Can Work: Kass shares how they intentionally deprioritized social commitments and accepted imperfection at home to build their company. She encourages other founder-parents to aim for 80%, not perfection, and to give themselves grace. Quote of the Show: "Being a founder, there’s no worse way to spend your day. And it’s awesome, right?" - Mike Lazerow Links: Kass’ LinkedIn: https://www.linkedin.com/in/kasslazerow/Mike’s LinkedIn: https://www.linkedin.com/in/lazerow/Get Their Book: https://shovelingshit.com/ Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #Shoveling$H!T Chapters: 00:00 Intro 00:46 Podcast Journey and Growth 01:41 Acknowledging Sponsors and Supporters 03:56 Introducing Cass and Mike Lazaro 05:33 Building Buddy Media: Key Strategies and Insights 08:19 Challenges and Successes in Leadership 14:09 The Importance of Transparency 15:19 Husband-Wife Co-Founders: A Unique Dynamic 20:09 Fundraising and Building Relationships 27:46 Marketing and Branding Strategies 34:09 Thought Leadership and Public Speaking 36:36 Navigating Business Pivots 38:25 The Birth of Buddy Media 40:31 Challenges and Successes of Custom Apps 45:20 Balancing Family and Business 48:50 Advice for Aspiring Entrepreneurs 54:58 Building a Positive Company Culture 01:02:21 Q&A with the Audience 01:11:11 Outro

    1h 12m
  6. Founders, Keepers - Tien Tzuo - Zuora - Episode #48

    JUN 10

    Founders, Keepers - Tien Tzuo - Zuora - Episode #48

    How do you scale yourself as your company scales? Tien Tzuo, Founder and CEO of Zuora, joins David Politis to share hard-won lessons from his journey building a category-defining SaaS company.  In this candid conversation, Tien reflects on early team building, founder growth inflection points, strategic planning, and the leadership gaps many founders face as their companies mature. Drawing on his new book, Founders Keepers, he reveals why great founders often succeed in spite of themselves—and how to turn blind spots into leadership strengths.   Takeaways: Category Creation and Team Building: Tien reflects on the impact of coining the term “subscription economy” and credits early success to not just vision, but team-building. He shares how Zuora evolved through multiple “generations” of leadership, and how long-tenured team members were balanced with fresh perspectives as the company grew.Recognizing the Founder’s Growth Curve: Tien describes a critical inflection point when Zuora hit ~150 employees—a moment where personal evolution became necessary. That led him to executive coach Rich Hagberg and a deeper understanding of how personality traits drive both success and failure.The Three Pillars of Leadership: Through data-driven leadership profiling, Tien outlines the three dominant founder traits—vision, execution, and relationships. He shares that most founders score high on vision but often struggle with execution and people management, which can lead to common pitfalls.Owning Your Leadership Gaps: Tien reveals his own leadership profile—high vision, medium execution, low relationship—and how understanding that helped him improve in areas like prioritization, team-building, and relationship development. He even shared his leadership gaps openly with his company to build trust and culture.A Better Way to Do Strategic Planning: Borrowing a method from Brad Smith (former Intuit CEO), Tien walks through how Zuora moved from a 2-day offsite to a 6-month annual strategy cadence. It includes deep research, team ownership of ideas, board engagement, and company-wide evangelism—because a founder’s job is to repeat the story until it sticks.Letting Go Without Losing Drive: He emphasizes the importance of giving leaders autonomy and building space into his calendar—cancelling recurring meetings, avoiding over-scheduling, and giving energy to what matters most. He advises founders to avoid being the bottleneck and protect organizational focus by saying “no” to distractions. Quote of the Show: "The same things that make up a founder, that make us do what we do, ultimately are the seeds sewn of our own destruction." - Tien Tzuo Links: LinkedIn: https://www.linkedin.com/in/tientzuo/Website: https://www.zuora.com/ Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #Zuora Chapters: 00:00 Intro 02:00 The Journey of Building Zuora 03:59 Scaling and Team Dynamics 07:43 Founder's Journey and Coaching 22:12 Strategic Planning and Execution 30:28 Frameworks for Strategic Alignment 32:33 Self-Awareness and Leadership 34:10 Execution-Oriented Teams 37:03 Lessons from Salesforce 38:07 The Power of Storytelling 40:59 Advice on Managing Time 43:33 Biggest Challenges and Overcoming Them 46:24 Future Vision for Zuora 48:22 Personal Journey and Motivation 52:33 Advice for Aspiring Founders 54:13 Outro

    56 min
  7. Balancing Experience and Innovation - John Swigart - Pie Insurance - Episode #47

    JUN 3

    Balancing Experience and Innovation - John Swigart - Pie Insurance - Episode #47

    How do you grow a startup into a transformative force in a highly regulated, slow-moving industry? John Swigart, Co-Founder and CEO of Pie Insurance, joins David Politis to discuss the importance of decisive leadership, the balance between founder intuition and executive delegation, and how execution at scale can be a long-term competitive advantage.  From assembling a thoughtful board to reorienting a business for profitability, John shares lessons from building a modern insurance company from scratch.   Takeaways: Decisiveness Around Leadership Transitions: John emphasizes making tough calls on leadership team members who may no longer be the right fit as a company evolves. Waiting too long creates compounding challenges and stalls progress.Balancing Founder Involvement with Delegation: He reflects on the “founder mode” concept, describing the need for leaders—founder or not—to stay close to the details while avoiding micromanagement. Clarity and context are key.The Decision-Making Matrix at Pie: John explains Pie’s internal framework for decision-making, which clearly defines who owns decisions, who contributes input, and how final calls are made—helping empower teams without chaos.Why Pie Competes in a Difficult Industry: Despite the dominance of legacy players in insurance, John saw a real opportunity: a fragmented market with outdated tech and poor customer experience. Pie’s modern, data-driven model aims to change that.Process Power as a Competitive Moat: Pie focuses on doing hundreds of small things better than the competition. John describes how consistent operational execution and better technology form a durable advantage over time.Adapting to a Profitability-Focused Environment: John details the major internal shift required when venture markets changed in 2022—from “grow at all costs” to sustainable, efficient operations. Layoffs and restructuring followed, but the business emerged stronger.Advice to His Younger Self: John would tell his younger self—and others early in their careers—to say yes to opportunities that offer growth. Don’t over-optimize for money or title; focus on learning and exposure instead.Quote of the Show: "Early in your career, optimize on learning growth, exposure, opportunity, not on money or title or, or anything of that nature." - John Swigart Links: LinkedIn: https://www.linkedin.com/in/johnswigart/Website: https://www.pieinsurance.com/ Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #PieInsurance Chapters: 00:00 Intro 01:42 Key Decisions and Leadership Challenges 07:24 Building and Evolving Leadership Teams 11:03 The Concept of Founder Mode 20:58 Competing in a Highly Regulated Market 31:13 Early Days and Customer Acquisition 31:53 Early Days of Multi-Channel Distribution 34:35 Fundraising Challenges and Successes 36:59 Building an Impressive Board 42:33 Navigating Business Challenges 48:39 Founding a Company Later in Life 53:46 Personal Growth and Mentorship 57:06 Pivotal Career Moments 01:00:48 Advice for Aspiring Entrepreneurs 01:02:17 Outro

    1h 3m
  8. Startups, AI, and Radical Honesty - Sasha Pasulka - Elka AI - Episode #46

    MAY 27

    Startups, AI, and Radical Honesty - Sasha Pasulka - Elka AI - Episode #46

    What happens when a strong vision, real traction, and early funding still aren’t enough? In this Failing Forward episode of Not Another CEO Podcast, Sasha Pasulka shares the journey behind her AI startup, Elka.  Sasha opens up about the thrill of building, the challenge of fundraising, the reality of launching with imperfect tech, and the emotional toll of shutting down a business you deeply believe in. From her days as a software engineer to founding one of the most-read blogs of its era, Sasha reflects on learning to trust herself, ask for help, and move on with grace.   Takeaways: The AI Aha Moment: Sasha was re-energized to found again after ChatGPT launched publicly in late 2022. She saw an opportunity to solve marketing problems that hadn’t been addressable before due to the language limitations of software.Solving a Real Problem from Experience: The product idea came from Sasha’s time at Tableau, where hours of valuable customer video content went unused because it was too hard to search. Elka aimed to automate finding and surfacing those insights for sales teams.Alpha and Beta Lessons: The team built fast and launched a beta early to help with fundraising, but users got frustrated with AI inconsistencies. Sasha onboarded every beta customer herself, but admits they may have opened access too soon.The Limits of Non-Deterministic Tech: Building on an LLM proved unpredictable. Despite numerous safeguards, the AI struggled with tasks like basic math and clip durations—issues Sasha says may have improved if they had more time to wait out tech advances.The Fundraising Wall: While Sasha successfully raised an angel round, later fundraising stalled. She reflects on her discomfort with the performative aspects of pitching and how authenticity may have hurt her in a system designed for bold salesmanship.Support and Disappointment: From angel investors to past coworkers, Sasha describes the surprising people who showed up to help—and the ones who didn’t. She credits her team, co-founder, and a few critical mentors with getting them as far as they did.Learning, Letting Go, and Looking Ahead: Sasha closes with advice to bring on a co-founder who can fundraise and a reminder to stop being intimidated by others’ confidence. She shares how the journey helped her understand her strengths and what she’ll do differently next time. Quote of the Show: "They may be in positions of power right now, but they're not necessarily smarter than you. They're not better than you… Don’t waste so much energy being intimidated by these people." - Sasha Pasulka Links: LinkedIn: https://www.linkedin.com/in/spasulka/TikTok: https://www.tiktok.com/@sashaiscooking Ways to Tune In: Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/  #NotAnotherCEO #BusinessSuccess #ElkaAI Chapters: 00:00 Intro 03:07 The Aha Moment: Founding Elka AI 04:30 Challenges in Marketing and AI Solutions 09:42 Building the Product: Alpha and Beta Phases 18:07 The Struggles of Fundraising and Leadership 25:22 Navigating Luck and Timing in Entrepreneurship 27:38 Key Decisions and Reflections 31:56 Navigating AI Non-Determinism 33:01 Support System and Key Influences 36:38 Fundraising Challenges and Lessons 42:40 Gender Dynamics in Fundraising 48:47 Personal Journey and Reflections 56:01 Advice for Future Founders 01:00:05 Outro

    1h 1m
5
out of 5
13 Ratings

About

Our mission is to bend the curve for Founders and CEOs. At Not Another CEO, we know there’s no formula for running a business. Leadership is forged through unique journeys, real challenges, and hard lessons. Our exclusive content showcases unfiltered stories and practical guidance from those who’ve crawled through the trenches. Our platform offers the largest library of CEO insights and how-to guides, sourced directly from a diverse community of leaders. Find our full video library, detailed playbooks, deep dives, and lessons learned on our Substack here ➡️ https://notanotherceo.substack.com/

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