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:

• Pioneering Global Expansion: Max's approach to expansion defies conventional paths. Instead of focusing solely on local markets like many Swedish companies, Max boldly decided to expand globally.
• The Power of Collaboration: Max stresses the importance of a shared mission between stakeholders and service providers, focusing on delivering unparalleled value and continuous improvement in legal services.
• Hiring and Culture Building: Max places a strong emphasis on ambition and cultural fit when hiring, believing these attributes are crucial for scaling a company. He maintains personal involvement in the interview process to ensure new hires align with the company’s high standards and growth trajectory.
• Learning and Growing from the YC Experience: Max’s experience with Y Combinator (YC) was transformative. Despite the complexities of maintaining operations during this period, the experience underscored the importance of mentorship and networking.
• Pushing the Envelope: Max underscores the importance of maintaining a proactive stance in innovation. By consistently exploring new pathways and pushing boundaries, he ensures the company remains at the forefront of technological advancements.

Quote of the Show:

• “ There's a real value in actually being the second mover, and the value comes from two things... You get to see what is the right path and what is the wrong path." - Max Junestrand

Links:

• LinkedIn: https://www.linkedin.com/in/maxjunestrand/
• Website: https://legora.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 #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:

• 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 #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:

• Scaling Begins with Small Wins: Flint emphasizes the importance of "stacking wins" in business, where each small victory propels you forward. He believes the key to success lies in maintaining momentum and making rapid, intelligent decisions.
• The Role of Mission and Values: For Flint, defining mission and values within a company is crucial for guiding decision-making processes. These elements serve as the company's moral compass, helping employees make decisions aligned with the organization's goals.
• Navigating Executive Leadership: Flint shares insights into the dynamics of leadership and succession planning. He describes the challenging process of evolving leadership roles to meet the company's growing demands.
• Overcoming Cybersecurity Challenges: Flint recounts a severe malware attack that tested the company's resilience. He stresses the importance of investing in robust cybersecurity measures and learning from such incidents to better protect critical business assets.
• The Power of Transparency: Flint argues for fostering trust and collaboration within the organization. By openly communicating challenges and strategies with his team, Flint was able to cultivate an environment of honesty and collective problem-solving.
• The Entrepreneurial Lifecycle: Flint illustrates the different stages of a company's growth, each with unique challenges and opportunities. From startup to public company, the journey requires adaptation and learning.
• Transitioning from Software to Sports: After two decades at Billtrust, Flint embarked on a new venture with Major League Table Tennis, driven by his passion for the sport.

Quote of the Show:

• “Any business is a combination of hundreds of thousands, if not millions of decisions, millions of small, little victories." - Flint Lane

Links:

• LinkedIn: https://www.linkedin.com/in/flintlane/
• Website: https://www.mltt.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 #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:

• 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 Patrick

Links:

• 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 #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

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 Mackey

Links:

• 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 #WinkyLux

Chapters:

00:00 Intro

01:23 Core Values and Company Culture at Winky Lux

11:28 The Importance of Customer Feedback

24:38 Challenges and Insights in Fundraising

33:32 The High Stakes of Venture Capital

35:06 The Changing Landscape of Entrepreneurship

36:37 The Role and Structure of YPO

40:00 Challenges and Resilience in Business

45:03 Future Prospects for Winky Lux

48:17 The Journey from Finance to Entrepreneurship

51:27 Mentorship and Community Support

59:11 Final Reflections and Advice

1:00:55 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 Kraus

Links:

• 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 #Lightship

Chapters:

00:00 Intro

01:46 The Importance of a Co-Founder Coach

02:28 Building a Strong Co-Founder Relationship

07:15 The Tesla Connection

14:38 Raising Capital During COVID

16:20 Challenges of Hardware Startups

24:00 Demonstrating Commercial Traction

26:50 Sales and Marketing Strategy

28:22 Hiring for Innovation

30:05 The Importance of Interviewing Candidates

30:39 Understanding the Common Failure Mode

32:02 The Value of Authentic Motivation

33:38 Emotional Runway vs. Cash Runway

34:31 Challenges in Building Lightship

37:38 Managing a Growing Team

40:40 Relinquishing Control and Trusting Your Team

44:00 Future Vision for Lightship

50:03 Balancing Work and Family Life

56:41 Reflecting on the Journey

58:21 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 Murphy

Links:

• 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 #Smartling

Chapters:

00:00 Intro

01:36 Embracing AI at Smartling

02:43 Implementing AI in a Production Environment

07:29 Customer-Centric Innovation

11:01 Understanding Customer Needs

24:25 Balancing Leadership and Involvement

31:37 Weekly Operating Rhythm

33:58 Strategic Planning and Key Initiatives

35:43 Balancing Focus and Resources

48:52 The Importance of Mentorship

51:40 Reflecting on Entrepreneurial Journey

54:06 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 Pedersen

Links:

• LinkedIn: https://www.linkedin.com/in/tbpeder
• Website: 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 #bunny

Chapters:

00:00 Intro

01:32 Building Bunny: Lessons from OneLogin

02:39 Team Dynamics and Hiring Strategies

05:59 Working with Family: A Brother's Partnership

10:55 Remote Work and Company Culture

16:40 Bootstrapping vs. Venture Capital

23:37 Marketing and Personal Branding

28:46 Passion for Solving Business Problems

31:21 The Importance of Solving Business Problems

31:38 Challenges and Solutions in Billing

33:24 Early Days of OneLogin

33:40 Building SAML Integrations

36:20 Acquiring First Customers for Bunny

37:35 The Role of Design Partners

41:28 Handling Security Breaches

45:04 Transparency and Customer Trust

48:09 Future of Bunny

50:46 Entrepreneurial Journey and Background

54:45 Mentorship

59:13 Advice to His Younger Self

01:03:04 Outro