Ask Why, Not Just What: The Ops Mindset Every Fund Needs

Accelerating Innovation: Cait Brumme on Social Capital and Startup Success

In this episode of Preferred Return, we sit down with Cait Brumme [https://www.linkedin.com/in/caitlin-reimers-brumme-4b098811/], CEO of MassChallenge [https://masschallenge.org/], to discuss how startups are tackling global challenges and why social capital is just as crucial as venture funding.  Cait reveals how MassChallenge is reshaping the accelerator model, focusing on connecting ambitious founders with the right resources, networks, and mentors. She shares stories of unexpected partnerships, like a biotech startup working with NASA to develop an artificial retina, and discusses the power of building a supportive founder community that helps entrepreneurs navigate the unpredictable startup journey. In this episode, you’ll learn: * The Power of Social Capital: Cait explains how MassChallenge helps startups thrive by prioritizing relationships and access to valuable networks over equity. * Navigating the Founder’s Journey: Learn why first-time founders often struggle with scaling and how MassChallenge’s support network helps them overcome these obstacles. * Building Resilience and Adaptability: Cait opens up about the emotional challenges of entrepreneurship and how peer support and learning from failure play a critical role in sustaining long-term success. Things to listen for: (00:00) Introduction to Cait Brumme (05:55) The role of social capital in supporting startup success (12:09) How MassChallenge nurtures first-time and frugal founders (16:43) The challenge of adopting AI and innovation within companies (23:52) The growth mindset: Balancing risk and security in organizations (31:50) The power of peer networks in entrepreneurial resilience (40:06) The global expansion of MassChallenge and new industry focuses (49:12) How alumni networks stay connected after MassChallenge programs (52:31) Advice for founders: Take risks, find support, and build a community Resources: More from Altvia: https://altvia.com/ [https://altvia.com/] Connect with Cait Brumme💡 LINKEDIN: https://www.linkedin.com/in/caitlin-reimers-brumme/ [https://www.linkedin.com/in/caitlin-reimers-brumme-4b098811/]

Magnetic. Unstoppable. Funded: Mastering the Art of the LP Meeting

In this episode of Preferred Return, we sit down with Craig Wortmann [https://www.linkedin.com/in/craigwortmann/], Founder of Sales Engine [http://www.salesengine.com], to discuss the habits, systems, and mindsets that define standout salespeople.  Drawing on three decades of experience as a founder, educator, and investor, Craig shares how deliberate practice, discipline, and relationship-building drive success in high-stakes conversations like fundraising and enterprise sales. He also opens up about a personal chapter—losing his leg to cancer—and how it reshaped his understanding of resilience, performance, and what it means to bounce back better. In this episode, you’ll learn: * How to Win the Room: Craig walks through the subtle disciplines—from meeting prep to handwritten notes—that make your meeting the one people remember. * The Mindset That Moves Deals: You’ll learn why sales isn’t about persuasion—it’s about helping people make progress in their lives. * What Elite Practice Really Looks Like: Learn the five elements of deliberate practice and why most people never actually improve. Things to listen for: (00:00) Introduction to Craig Wortmann (02:23) Wearing three hats: Sales Engine, Kellogg, and venture partner (09:20) Self-disqualifying: Why cultural fit matters in sales (16:02) How to stand out in a sea of 35 weekly meetings (24:23) Asking better questions: Start the conversation, not a pitch (32:55) The power of a handwritten thank-you note in sales (36:58) Hiring for growth: Why coachability beats experience (45:11) Deliberate practice: What separates good from great (49:12) Lifequake to learning: Craig’s cancer and resilience journey (53:44) The Bounce Back Better framework for adversity (59:08) Master Course Academy and why teaching is still learning Resources: * More from Altvia: https://altvia.com/ [https://altvia.com/] Connect with Craig Wortmann💡 LInkedIn: https://www.linkedin.com/in/craigwortmann/ [https://www.linkedin.com/in/craigwortmann/]  If you're interested in learning more about the services at Sales Engine, please visit their website at www.salesengine.com [http://www.salesengine.com/].

Ask Why, Not Just What: The Ops Mindset Every Fund Needs

In this episode of Preferred Return, we’re joined by Lauren Schirle [https://www.linkedin.com/in/lauren-schirle/], Senior Manager - Strategic Initiatives at VIRIDIS Fund Solutions [https://viridisfs.com/], where she reveals how to maximize the true potential of data. With a career that bridges the worlds of archival sciences, technology, and finance, Lauren explains how organizing and presenting data is essential for both business decision-making and making historical stories accessible. She talks about her journey from working with archival data to helping companies manage financial information better, showing how well-structured data can tell powerful stories. In this episode, you’ll learn: * How to Turn Raw Data Into Actionable Insights: Lauren explains the key steps for organizing data, allowing businesses to make informed decisions. * Why Data Quality Matters More Than You Think: Learn why accurate and clean data is essential for generating reliable analytics. * The Critical Skills You Need to Maximize Data Access: Teaching people to ask the right questions can empower teams to use data more effectively. Things to listen for: (00:00) Introduction to Lauren Schirle (02:33) From history and economics to managing $30 billion (05:16) Data as storytelling: Making historical information accessible (06:49) Building systems for accessible data in business contexts (12:50) Information literacy: Asking better questions in business (17:12) User interaction as a series of questions (18:45) Lessons from operational roles and historical data work (37:16) The evolving role of information literacy across industries (48:20) Advice for GPs: Ensuring data quality and understanding data tools (52:57) Trends in portal technology and future directions (55:27) Personal growth through questioning and diverse perspectives Resources: * More from Altvia: https://altvia.com/ [https://altvia.com/] Connect with Lauren Schirle💡 LINKEDIN: https://www.linkedin.com/in/lauren-schirle/ [https://www.linkedin.com/in/lauren-schirle/]

The Art of Seeing What Others Miss: An "Outsider's" View of Private Equity

In this episode of Preferred Return, we sit down with Usamah Khan [https://www.linkedin.com/in/usamahk/], Vice President of Data & Technology at White Star Capital [https://whitestarcapital.com/], to explore the intersection of technology, venture capital, and data-driven decision-making.  Usamah shares his unconventional journey from engineering and startups to venture investing, revealing how his background in data analytics and product development helps White Star assess and support portfolio companies. He breaks down the role of technical due diligence, the challenges of AI adoption, and the unique CTO-to-CTO conversations that set White Star apart in venture investing. In this episode, you’ll learn: * How Technical Due Diligence Shapes Investment Decisions: Usamah explains how White Star evaluates technology startups, identifies red flags, and determines what makes a product defensible. * The Adoption Challenge in AI: Discover why AI tools often struggle to deliver ROI and what it really takes for businesses to integrate AI successfully. * The Power of Data in Venture Capital: Learn how White Star leverages data insights to track potential investments, monitor portfolio performance, and support founders beyond capital. Things to listen for: (00:00) Introduction to Usamah Khan (01:11) From engineering to venture capital (04:08) Early startup lessons in data analytics (05:51) Building smart city tech at Umbrellium (08:33) The COVID pivot that changed everything (10:24) Finding his way to White Star Capital (12:07) Pitching his own role and making it fit (13:58) How White Star evaluates technology (17:45) Spotting red flags in early-stage startups (20:41) Unifying portfolio insights with data (24:54) Using AI signals to track investments (29:57) The real challenge with AI adoption (40:04) What CTO-to-CTO talks really uncover (45:52) Supporting founders beyond capital (55:08) Advice for breaking into venture capital Resources: More from Altvia: https://altvia.com/ [https://altvia.com/] In this episode, you’ll learn: Connect with Usamah Khan💡 LinkedIn: https://www.linkedin.com/in/usamahk/ [https://www.linkedin.com/in/usamahk/]

Building a Fintech Startup from Scratch: Jack Boudreau on Raising Capital and Taking Big Bets

In this episode of Preferred Return, we sit down withJack Boudreau [https://www.linkedin.com/in/jack--boudreau/], Co-Founder & CEO ofHabits [https://www.usehabits.com/], to explore the challenges and triumphs of building a fintech startup from the ground up. Jack shares his journey from JPMorgan to launching Habits, a platform that connects young professionals with financial advisors, breaking down the barriers to financial guidance. He opens up about the realities of fundraising, the lessons learned from hearing ‘no’ hundreds of times, and how resilience and adaptability have shaped his approach to building Habits. In this episode you'll learn: * The Realities of Raising Capital:Jack reveals what it takes to fundraise successfully, from pitching VCs to securing investment from early users. * Why Financial Planning is Broken for Millennials & Gen Z:Discover how shifting financial habits and trust in digital communities are changing the advisor landscape. *  The Startup Mentality That Drives Success:Learn why chasing rejection, embracing uncertainty, and staying close to your customers are key to building a company that lasts. Things to listen for: (00:00) Introduction to Jack Boudreau (01:13) Raising $1.1M pre-seed with Atlanta Ventures (03:16) Why trust in finance is shifting to digital communities (05:25) The rise of YouTube and TikTok as financial educators (07:16) Leaving JPMorgan: The moment Jack took the leap (09:31) Spotting an untapped market for financial guidance (11:18) Bootstrapping Habits to $100K ARR before raising (13:19) Fundraising realities: Hearing ‘no’ 99 times out of 100 (16:23) Pitching investors at 6:30 AM while on the road (22:24) How pitching an angel vs. a VC is completely different (26:28) Learning how to pivot while keeping investors aligned (30:49) Staying close to customers and evolving the product (42:41) The mental toll of entrepreneurship and resilience (53:44) Advice for taking the leap: Chase the hard things (01:00:32) Why Habits is just getting started Resources: * More from Altvia:https://altvia.com/ [https://altvia.com/] Connect with Jack Boudreau 💡 LINKEDIN:https://www.linkedin.com/in/jack--boudreau/ [https://www.linkedin.com/in/jack--boudreau/]