In this episode of Tech Scenes, Jeff James Martin sits down with Jennifer Henderson, Founder & CEO of Tilt, to discuss the challenges and innovations in leave management, the startup journey, and the role of female founders in venture capital.

Jennifer shares her personal experiences that led to the creation of Tilt, an HR tech platform designed to automate and streamline leave of absence management, making the process easier for both companies and employees. “We are obsessed with the world of leave.” The conversation dives deep into the complexities of leave compliance, the transition from corporate to startup life, and the importance of company culture in a fast-growing business.

They also discuss the unique challenges faced by female founders when raising capital, why more encouragement is needed for aspiring women entrepreneurs, and how guardrails in business help create efficiency and empowerment. Jennifer emphasizes resilience as a key trait for successful founders, while also sharing some fun personal reflections on her love for 80s music.

"You gotta imagine you're going down a road." – Jennifer on why businesses need clear guardrails for efficiency and success.

"Unless you win the manager jackpot." – Discussing the inconsistencies in how companies handle leave management.

"The pain becomes untenable is getting smaller." – On how Tilt is removing the biggest pain points in HR processes.

"We need more points on the board." – Jennifer advocating for more female entrepreneurs in venture-backed startups.

"Def Leppard is my childhood in every single song." – A fun conclusion to a deeply insightful conversation.

From navigating startup challenges to building a strong company culture, this episode is packed with valuable lessons for entrepreneurs, HR professionals, and anyone passionate about improving employee experiences.

Key Takeaways:

- Guardrails in business help maintain clarity and efficiency, preventing wasted effort.

- Tilt automates leave management, saving organizations time, money, and compliance headaches.

- Personal experiences often drive innovative business solutions, as seen in Tilt’s founding story.

- Leave management is highly complex, varying based on individual circumstances, company policies, and legal compliance.

- Transitioning from corporate to startup requires a different skill set, with steep learning curves for first-time founders.

- Building a strong company culture is essential for long-term startup success.

- Female founders face unique challenges in securing venture capital, requiring persistence and strong networks.

- Encouragement and role models are crucial for inspiring the next generation of female entrepreneurs.

- Resilience is key in the entrepreneurial journey, especially when navigating challenges like funding and scaling.

Chapters:

0:00 - The Importance of Guardrails in Business

2:07 - Understanding Tilt: Revolutionizing Leave Management

5:01 - Personal Experiences Shaping Business Solutions

9:48 - Navigating the Complex Landscape of Leave Management

15:08 - The Journey from Corporate to Startup

19:46 - Building a Strong Company Culture and Team Dynamics

24:51 - Challenges for Female Founders in Venture Capital

29:49 - Encouraging Future Female Entrepreneurs

34:59 - Final Thoughts and Reflections

Don’t forget to like, subscribe, and hit the notification bell to stay updated with all our episodes, where we bring you the untold stories of innovation and leadership from the tech world, only on Tech Scenes.

Learn more about the book Peak Teams - Mastering the Habit of Unstoppable Venture-backed Companies - https://a.co/d/hp5Jtnu

Visit Collective Genius™ to Build Your Venture-backed Team with the Peak Operating System™ - https://www.collective-genius.com/

Music by Andrew Applepie - https://soundcloud.com/andrewapplepie

#TechScenes #Tilt #LeaveManagement #HRTech #FutureOfWork #StartupLife #ScalingStartups #Leadership #WomenInTech #Entrepreneurship #FemaleFounders

In this episode of Tech Scenes Unplugged, Jeff James Martin sits down with Alex Jekowsky, CEO and Co-founder of Cents, to discuss the realities of startup life, building technology for unsexy industries, and transforming the laundry industry with product-led innovation.Alex shares his journey as a second-time founder, explaining how he turned his passion for simplifying everyday problems into scalable businesses. With Cents, he’s building a network of garment care SMBs, empowering local laundromats and dry cleaners to take back laundry day in America through centralized technology and streamlined operations.This conversation dives into the critical role of customer-driven product development, the importance of guiding principles in shaping company culture, and fostering open communication to build high-performing teams. Alex also shares key lessons from fundraising, why startups require mental resilience, and how happiness in the workplace is crucial for long-term success."It’s not worth it if you don’t enjoy it." – Alex on why founders must love the grind of building a company.

"Act like an owner, not just a shareholder." – A mindset shift that drives real business success.

"Fundraising is not a vanity metric." – Alex discusses the dangers of chasing investment for the wrong reasons.

From hiring practices rooted in core values to scaling through optionality and efficiency, this episode is packed with practical takeaways for entrepreneurs and business leaders alike.Key Takeaways:Startups should be enjoyable—if you don’t love the process, it’s not worth it.Enduring challenges and pain is part of the entrepreneurial journey—it builds perseverance.Creating centralization and optionality empowers SMBs—helping them scale more efficiently.Customer relationships drive product development—listening to their needs shapes the roadmap.Act like an owner—this mindset enhances business success at every level.Guiding principles align the entire company—they provide clarity in decision-making.A selfish environment creates dysfunction—team success depends on alignment.Open communication is essential for high-performing teams—transparency fosters trust.Fundraising is not a vanity metric—it's a tool, not an end goal.A learning culture is key to scaling a startup successfully—leaders must continuously grow.Happiness is a choice in the workplace—building a positive culture leads to better outcomes.

Chapters:0:00 - The Reality of Startups and Small Business Ownership2:11 - Understanding Cents and Its Mission5:06 - Transforming the Laundry Industry with Technology10:01 - Product Roadmap and Customer-Centric Development15:47 - Guiding Principles and Company Culture22:04 - Fostering Open Communication and Team Dynamics29:34 - Building a Culture of Happiness30:01 - Establishing Guiding Principles31:59 - Core Values and Hiring Practices33:06 - High-Performing Team Behaviors34:29 - Enduring Pain for Growth36:23 - Navigating Fundraising Challenges39:25 - Lessons from Second-Time Founders40:41 - Personal Development and Leadership42:55 - Creating a Learning Culture45:44 - The Importance of Happiness in Teams50:34 - Final Thoughts and Desert Island AlbumDon’t forget to like, subscribe, and hit the notification bell to stay updated with all our episodes, where we bring you the untold stories of innovation and leadership from the tech world, only on Tech Scenes Unplugged.Learn more about the book Peak Teams - Mastering the Habit of Unstoppable Venture-backed Companies https://geni.us/peak-teams Visit Collective Genius™ to Build Your Venture-backed Team with the Peak Operating System™ https://www.collective-genius.com/ Music by Andrew Applepie - https://soundcloud.com/andrewapplepie#TechScenes #Cents #StartupLife #Entrepreneurship #SmallBusiness #LaundryTech #Leadership #jeffjamesmartin #AlexJekowsky #ProductLedGrowth #CustomerSuccess

In this episode of Tech Scenes Unplugged, Jeff James Martin sits down with Ethan Austin, Founding Partner of Outside VC, to discuss venture capital, outsider founders, and the power of community and empathy in investing. Outside VC is a pre-seed venture firm dedicated to supporting founders outside traditional funding networks, with the goal of lifting 100M people to the middle class over the next decade. The conversation explores the challenges faced by non-traditional founders, the role of peer learning and transparency in venture, and the importance of investing in people over ideas. Ethan also shares insights on mental health for entrepreneurs, scaling teams effectively, and the impact of AI on business operations. Key Takeaways: Venture capital is not a meritocracy—outsider founders often build the best businesses. Founders want investors they connect with, not just those proving they’re smart. Community and peer learning play a crucial role in founder success. Empathy and transparency are essential in venture capital relationships. Fun matters in the startup journey—not everything has to be serious. Mental health is a superpower—sleep, stress management, and mindset shape success. AI is transforming venture capital and how startups scale. Employee equity structures need reform to better reward workers. Exceptional founders focus on execution, not just ideas. Reverse engineering success helps entrepreneurs navigate long-term growth. YouTube Chapters: 0:00 - The Human Element in Venture Capital 3:09 - The Journey of Outsider Founders 6:08 - The Role of Community in Entrepreneurship 9:13 - Investing: A Passion for Supporting Founders 11:57 - The Impact of Personal Background on Entrepreneurial Drive 14:49 - Empathy and Transparency in Venture Capital 18:03 - The Importance of Fun in the Startup Journey 28:05 - Investing in People, Not Just Companies 30:06 - Mental Health Strategies for Entrepreneurs 31:27 - The Role of Empathy in Venture Capital 32:57 - Building Effective Teams in Startups 36:10 - Reverse Engineering Success 40:04 - The Importance of Mission and Vision 41:50 - Building the Engine to Scale 43:59 - Key Traits for Investment 46:07 - Navigating AI in Business 47:51 - Employee Equity and Fairness 51:01 - Desert Island Album Choice Don’t forget to like, subscribe, and hit the notification bell to stay updated with all our episodes, where we bring you the untold stories of innovation and leadership from the tech world, only on Tech Scenes Unplugged. Learn more about the book Peak Teams - Mastering the Habit of Unstoppable Venture-backed Companies - https://a.co/d/hp5Jtnu Visit Collective Genius™ to Build Your Venture-backed Team with the Peak Operating System™ - https://www.collective-genius.com/ Music by Andrew Applepie - https://soundcloud.com/andrewapplepie #TechScenes #OutsideVC #VentureCapital #StartupGrowth #Entrepreneurship #Investing #jeffjamesmartin #EthanAustin #FounderSupport #AI #ProductLedGrowth