Not Another CEO Podcast

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:Multi-Product Strategy Innovation: Nick emphasized Radar's growth through expanding their product offerings rather than focusing on a singular solution. By catering to diverse customer requests, Radar transitioned from a geo-fencing platform to a comprehensive location service provider.Customer-Centric Approach: Nick underlined the importance of being customer-driven in product development. Radar has prioritized building what customers request, as long as it aligns with their overall vision.Modernizing Company Culture: Radar has seen increased cohesion and morale by embracing a focused mission and maintaining a workplace culture that emphasizes teamwork over rigid organizational roles.Leadership through Uncertainty: Leading through the pandemic, Radar faced significant challenges with clients from the travel and retail sectors. The company pivoted by redefining its strategy, focusing on delivering multiple product solutions, strengthening its market position.The Shift from Remote Work Culture: While embracing remote work during the pandemic, Nick advocated for in-person collaboration as a competitive advantage. By returning to office-based work, Radar has fostered a more cohesive culture and quicker iteration of ideas.Strategic Fundraising Tips: Nick shared valuable insights into securing investment, noting the importance of creating urgency during fundraising and finding investors who truly “get” the company's vision.Quote of the Show:“Either people happen to Radar or Radar happens to them… you wanna hire people like they happen to Radar." - Nick PatrickLinks:LinkedIn: https://www.linkedin.com/in/nicholaspatrick/ Website: https://radar.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 #RadarChapters:00:00 Intro01:12 The Impact of Multi-Product Strategy03:16 Challenges and Management of Multi-Product Approach07:43 Product Involvement and Team Structure12:30 Customer-Centric Engineering14:42 In-Person Collaboration and Office Culture19:52 Founding Radar and Early Challenges28:36 Fundraising Journey and Investor Relations34:55 Navigating Business Through Uncertain Times35:47 Adapting to Market Changes and Setting Expectations38:20 Cultural Shifts and Social Issues41:21 Future Vision for Radar43:24 Personal Journey and Entrepreneurial Spirit47:38 Balancing Work and Family Life51:03 Advice for Aspiring Entrepreneurs54:25 Outro

What happens when you jump from a career in finance to tackling the beauty industry? In this episode, Natalie Mackey shares her reflections on building Winky Lux, from bootstrapping to private equity. She opens up about the importance of core values, the challenges of fundraising as a female founder, and the lessons she learned navigating through different growth stages. Takeaways:Importance of Core Values: Natalie emphasizes the transformative impact of clearly defined core values in the evolution of Winky Lux. The company started with general ideals, but crystallizing specific values became vital as the company scaled.Consumer-Centric Approach: A pivotal moment in Winky Lux's development was the decision to pivot from a marketplace to a full-fledged brand. This shift was entirely consumer-driven, based on insights gathered from direct customer interactions.Fundraising Challenges: Natalie candidly discusses the journey of fundraising, particularly as a female founder. Despite the competitive landscape and systemic biases, she underscores the importance of perseverance and strategic financial planning.Brand Aesthetics and Market Trends: Natalie delves into the significance of aesthetics in the beauty industry. She describes Winky Lux's vibrant, art-inspired branding, which aligns with current market trends.Embracing Community and Collaboration: Natalie credits a considerable part of her success to the entrepreneurial community, highlighting how networks like YPO foster invaluable support and collaboration.Quote of the Show:“I don't mind swinging and striking out, but I really, really, really hate not having swung." - Natalie MackeyLinks:LinkedIn: https://www.linkedin.com/in/natalie-mackey-15169370/  Website: https://winkylux.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 #WinkyLuxChapters:00:00 Intro01:23 Core Values and Company Culture at Winky Lux11:28 The Importance of Customer Feedback24:38 Challenges and Insights in Fundraising33:32 The High Stakes of Venture Capital35:06 The Changing Landscape of Entrepreneurship36:37 The Role and Structure of YPO40:00 Challenges and Resilience in Business45:03 Future Prospects for Winky Lux48:17 The Journey from Finance to Entrepreneurship51:27 Mentorship and Community Support59:11 Final Reflections and Advice1:00:55 Outro

What does it take to leave a high-profile role at Tesla and start your own electric vehicle company? In this episode, David talks with Toby Kraus, Co-Founder and CEO of Lightship, about his journey from working on Tesla’s Model S to building an innovative electric RV startup. Toby shares insights on taking big risks, scaling early teams, and navigating the challenges of a hardware business in the EV space. They dive into lessons learned at Tesla, the importance of building trust with investors, and the unique market opportunity Lightship is chasing. Takeaways:The Importance of Coaching: Toby emphasized the value of having a co-founder coach to strengthen the relationship between company leaders. He and his co-founder began working with a coach from the beginning, which Toby credits with helping them maintain a strong partnership and navigate the pressures of building Lightship.Adapting to Growth: As Lightship expanded, managing a larger team and aligning everyone with the company’s mission became a significant challenge. Toby learned that relinquishing control and trusting team experts were vital to maintaining momentum and effectiveness.Venture Capital Challenges: While their early seed round was successful, each subsequent round of funding became increasingly difficult, highlighting the unique challenges hardware companies face compared to software firms, as venture capitalists often favor faster software cycles.Creating a Culture of Ownership: Creating opportunities for team members to take ownership of projects fosters an environment of trust. By delegating responsibilities and empowering team members, leaders convey confidence in their team’s capabilities.Grateful of the Bumpy Path: Despite the mistakes and challenges he faced, Toby insists that changing any aspect of his journey might not have led to the founding of Lightship. Each experience, no matter how difficult, contributed to his current success and perspective.Quote of the Show:“My hidden agenda is I want to know why you wanna work here." - Toby KrausLinks:LinkedIn: https://www.linkedin.com/in/tobykraus/  Website: https://www.lightshiprv.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 #LightshipChapters:00:00 Intro01:46 The Importance of a Co-Founder Coach02:28 Building a Strong Co-Founder Relationship07:15 The Tesla Connection14:38 Raising Capital During COVID16:20 Challenges of Hardware Startups24:00 Demonstrating Commercial Traction26:50 Sales and Marketing Strategy28:22 Hiring for Innovation30:05 The Importance of Interviewing Candidates30:39 Understanding the Common Failure Mode32:02 The Value of Authentic Motivation33:38 Emotional Runway vs. Cash Runway34:31 Challenges in Building Lightship37:38 Managing a Growing Team40:40 Relinquishing Control and Trusting Your Team44:00 Future Vision for Lightship50:03 Balancing Work and Family Life56:41 Reflecting on the Journey58:21 Outro

What does it take to drive significant transformation in a tech company? In this episode, David interviews Bryan Murphy, the seasoned entrepreneur and current CEO of Smartling. Murphy shares insights into his strategic decision to integrate AI rapidly at Smartling, the challenges faced in execution, and the creation of a separate R&D function to innovate without disrupting core operations. Murphy discusses his approach to leadership, the impact of meeting with hundreds of customers, and the critical role of operational discipline. Additionally, he reflects on his entrepreneurial journey, from his early ventures to his mentoring experiences and the factors driving his unyielding ambition.  Takeaways:Embracing Innovation and AI: Bryan emphasizes the importance of being early adopters of AI in order to remain competitive. He recounts how Smartling's leadership team proactively engaged with AI technologies as soon as they became available. Cultivating Customer Obsession: A significant part of Bryan's approach as CEO involves a deep focus on understanding and anticipating customer needs. He actively engages with customers, often initiating conversations with questions about the primary problems they are trying to solve.Building a Robust Operating Rhythm: Bryan highlights the critical role of a structured operating rhythm in executing plans effectively. Weekly leadership and management council meetings at Smartling help streamline processes and keep initiatives on track.Strategic Decision-Making in Remote Work Setup: With over 200 employees across 20 countries, Bryan holds annual gatherings and regular meet-ups to foster team cohesion while accommodating the global distribution of the workforce.Clarifying Business Metrics and KPIs: To Bryan, measuring success involves defining clear Key Performance Indicators (KPIs) that are aligned with customer value. These metrics directly inform product development and strategic priorities, ensuring the company remains focused on delivering value to customers.Overcoming the Innovator’s Dilemma: Bryan explains the challenge of balancing innovation with existing successful practices, a common issue known as the innovator's dilemma, by systematically integrating new technologies like AI to improve its service offerings without destabilizing its well-established operations.Advice for Aspiring Leaders: Bryan advises newcomers to the industry to always meet their obligations first and then seek opportunities to contribute more broadly, ensuring career advancement and sustained organizational impact.Quote of the Show:“[CEOs] have that latitude to run across the organization and dive down into each one of the respective parts of the organization, no one else can do that or does do that." - Bryan MurphyLinks:LinkedIn: https://www.linkedin.com/in/bryanmurphy2/Website: https://www.smartling.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 #SmartlingChapters:00:00 Intro01:36 Embracing AI at Smartling02:43 Implementing AI in a Production Environment07:29 Customer-Centric Innovation11:01 Understanding Customer Needs24:25 Balancing Leadership and Involvement31:37 Weekly Operating Rhythm33:58 Strategic Planning and Key Initiatives35:43 Balancing Focus and Resources48:52 The Importance of Mentorship51:40 Reflecting on Entrepreneurial Journey54:06 Outro

What’s it really like to build a SaaS company from scratch, not just once but twice? In this episode, David talks to Thomas Pedersen, the serial entrepreneur who co-founded OneLogin and now leads Bunny, a bootstrapped billing platform for B2B SaaS.Thomas also opens up about co-founding two companies with his brother, surviving a major security breach, and how he’s approaching company-building differently this time around. Takeaways:Why Thomas Is Bootstrapping This Time: After raising $175 million for OneLogin, Thomas opted to bootstrap Bunny, focusing on control and long-term product quality. He discusses how this choice affects hiring, spending, and overall company culture.Bringing the Band Back Together: Bunny’s small but mighty team includes engineers from OneLogin. Thomas shares why working with trusted colleagues has helped them execute quickly and avoid early hiring pitfalls.The Grind Creates the Bond: Reflecting on the early OneLogin years, Thomas explains how hard work and shared struggle helped forge lasting relationships and why people often want to work with him again.Building with His Brother, Again: Thomas co-founded both of his startups with his brother. He explains how they complement each other technically, navigate disagreements, and have grown even closer through the experience.Remote from Day One: From commuting weekly between LA and San Francisco during OneLogin’s VC-fueled growth to now working from a boat in the Mediterranean, Thomas discusses why Bunny is remote-first and when in-person still matters.Lessons from a Security Breach: A major breach at OneLogin could have destroyed the company. Thomas details how transparency and direct communication with customers helped them retain trust and bounce back.Quote of the Show:"It’s really hard to get a design partner… I wish every Saas or every startup could find a customer like that." - Thomas PedersenLinks:LinkedIn: https://www.linkedin.com/in/tbpederWebsite: https://bunny.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 #bunnyChapters:00:00 Intro01:32 Building Bunny: Lessons from OneLogin02:39 Team Dynamics and Hiring Strategies05:59 Working with Family: A Brother's Partnership10:55 Remote Work and Company Culture16:40 Bootstrapping vs. Venture Capital23:37 Marketing and Personal Branding28:46 Passion for Solving Business Problems31:21 The Importance of Solving Business Problems31:38 Challenges and Solutions in Billing33:24 Early Days of OneLogin33:40 Building SAML Integrations36:20 Acquiring First Customers for Bunny37:35 The Role of Design Partners41:28 Handling Security Breaches45:04 Transparency and Customer Trust48:09 Future of Bunny50:46 Entrepreneurial Journey and Background54:45 Mentorship59:13 Advice to His Younger Self01:03:04 Outro

Do you know the key factors for successful leadership in high growth tech companies? In this episode, CEO of commercetools Andrew Burton shares his extensive experience in building and scaling tech companies. With over 25 years in the industry, Burton details his approach to leadership since becoming CEO of commercetools in 2024. He emphasizes the paramount importance of maintaining customer focus, building strong team culture, and aligning company goals.  Takeaways:Understanding Customer Needs: Andrew highlights the importance of stepping into customers' shoes to understand their challenges and measure success through their lens. He emphasizes starting conversations by asking customers about their challenges and how they define success.Aligning Around an Ideal Customer Profile: A crucial step Andrew implemented at commercetools was refining their Ideal Customer Profile (ICP). He stresses the necessity of focusing on where the company can deliver the most significant value and understanding why they're uniquely positioned to serve that particular segment.The Role of Leadership in Team Development: Andrew believes in playing as one team and ensuring a unified direction across the organization. He discusses the importance of testing for cultural and operational inconsistencies as a new CEO and aligning the team around shared objectives and metrics. Strategic Planning and Adapting to Change: Andrew shares insights into effective strategic planning by decoupling it from the stress of annual closing and starting a new fiscal year.Curiosity as a Driver for Success: Andrew describes how a curious approach to understanding problems and developing solutions leads to personal and organizational growth, making it a critical quality he looks for when hiring team members.Balancing Passion and Work-Life Integration: Andrew touches on the concept of work-life balance, suggesting that it is deeply connected to one's passion and motivation. He encourages individuals to be mindful of what genuinely drives them and to regularly assess whether their professional and personal lives are aligned with these motivations.Mentorship and Learning from Diverse Experiences: Andrew reflects on his journey and the importance of mentorship, emphasizing that learning from a variety of experiences and colleagues, regardless of hierarchy, contributes to a well-rounded leadership style.Quote of the Show:"Anybody that's really, I would argue successful… in their space, is going to know or have an appreciation for, at the core, the customer." - Andrew BurtonLinks:LinkedIn: https://www.linkedin.com/in/burtonandrew/Website: https://commercetools.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 #commercetoolsChapters:00:00 Intro01:58 The Importance of Customer-Centric Leadership04:21 Engaging with Customers: Strategies and Insights09:36 Aligning Company Mission and Team Goals13:10 Defining the Ideal Customer Profile (ICP)17:50 Building Trust and Credibility as a New CEO23:15 Strategic Planning and Measuring Success31:50 Monthly Cadence and Operational Efficiency33:05 Reflections on Planning and Offsite Meetings34:50 Journey to Becoming a CEO35:58 Curiosity and Leadership43:44 Mentorship and Influences46:24 Hiring and Growth Mindset51:43 Future of Commerce Tools53:36 Personal Background and Motivation56:59 Work-Life Balance and Career Advice01:01:48 Outro

What happens when you commit to shipping a podcast episode every week for an entire year? In this solo episode, David Politis reflects on 12 months of building Not Another CEO Podcast, from humble beginnings to an ever-growing audience of Founders, CEOs, and leaders. David shares 10 of his favorite highlights from the journey so far, covering everything from guest stories and personal milestones to the behind-the-scenes evolution of the show. This episode is a heartfelt thank-you to the community that has grown around the podcast and a look ahead at what’s next. 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 #Podcast #1YearReflection

What does it take to transform a scrappy logistics startup into a leading supply chain platform trusted by Fortune 500 brands? In this episode, Sean Henry shares the story of founding Stord, dropping out of college to build it, and scaling a distributed logistics network from zero to national reach. He opens up about fundraising setbacks, building conviction in tough moments, keeping customer experience front and center, and navigating the pressure of rapid growth while staying anchored in purpose. Takeaways:Dropping Out to Go All-In: Sean left college to pursue Stord full time, driven by a conviction that there was a better way to manage logistics in a fragmented industry. That early decision required grit and belief before traction or investor backing.Turning Cold Outreach Into Capital: Sean shares how his early fundraising relied on writing 150 cold emails a day. Persistence and storytelling helped him break through, eventually leading to key early checks that helped kickstart Stord’s growth.The Importance of Mission and Mindset: Through tough moments and early challenges, Sean and his Co-Founder stayed grounded in their mission. He talks about the psychological weight of leadership and the discipline required to keep moving forward.From Scrappy Marketplace to Full Stack Platform: Stord started as a logistics marketplace but pivoted into a fully integrated supply chain solution. Sean explains how that shift allowed them to deliver better customer experience, tighter control, and long-term defensibility.Customer Experience Is the Product: Even as a logistics company, Sean believes customer experience is the most important differentiator. He shares how Stord built systems and culture that put CX at the center of every part of the business.Navigating the Growth Curve Without Losing Focus: Sean discusses what it’s like to scale quickly while holding on to high standards. He shares lessons around team building, leadership habits, and making time for clarity amid the noise.Believe, But Be Realistic: Sean reflects on the importance of conviction, but also warns Founders to avoid believing their own hype. He recommends surrounding yourself with people who keep you honest and grounded as you grow.Quote of the Show:"If we don't have a customer, we don't have employees. If we have a vision but have no customers, that vision means nothing." - Sean HenryLinks:LinkedIn: https://www.linkedin.com/in/shenry96/Website: https://www.stord.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 #StordChapters:00:00 Intro01:49 The Importance of Customer Obsession05:44 Hiring for Customer Obsession10:19 Scaling and Company Culture21:30 Early Challenges and Pivots39:26 The Rise and Fall of the Trucking Network40:23 Navigating Hard Decisions and Growth42:50 Investor Relations and Fundraising Journey44:11 Mentorship and Early Influences45:33 Strategic Partnerships and Business Alignment51:23 Overcoming Challenges and Turning Points56:10 Future Vision and Expansion Plans01:03:51 Personal Background and Entrepreneurial Spirit01:13:14 Advice to His Younger Self1:14:40 Outro

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 RubinLinks: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 #CauselyChapters:00:00 Intro01:45 Key to Startup Success: Building the Right Team03:08 Exposing Team Members to the Bigger Picture06:08 Encouraging Curiosity and Engagement09:45 Supporting Women in Technology15:03 Challenges in the Tech Industry17:50 The Boston Tech Ecosystem21:37 Importance of Local Community in Remote Work Era27:08 Customer Engagement and Feedback30:07 Effective Operating Rhythms35:23 Lessons from Amazon37:50 Navigating the M&A Process38:31 Deciding the Right Time to Sell40:59 Taking Calls from Corporate Development44:30 The AI Revolution: A 70-Year Overnight Sensation46:00 The Role of AI in Modern Enterprises01:01:58 The Importance of Mentorship01:06:25 Balancing Entrepreneurship and Family01:09:13 Advice for Aspiring Entrepreneurs1:10:27 Outro

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 RichheimerLinks: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 #LawftyChapters:00:00 Intro01:41 The Importance of Complementary Skill Sets02:41 Finding a Co-Founder in an Unlikely Place03:44 Building Lawfty: From Idea to Execution06:19 Challenges and Strategies in Team Building09:29 Navigating the Interview Process12:47 Understanding Lawfty’s Business Model16:26 Early Customer Acquisition Tactics20:57 Fundraising Journey and Lessons Learned26:38 Scaling as a CEO29:31 The Legal Tech Revolution32:09 Challenges in Legal Services34:52 Building a Tech-Enabled Law Firm37:14 Overcoming Industry Stigma42:35 Fundraising Challenges and Solutions47:01 Personal Journey and Entrepreneurial Drive54:12 Advice for Aspiring Entrepreneurs56:48 Outro