In this episode of Preferred Return, we sit down with Cait Brumme, CEO of MassChallenge, 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:

In this episode of Preferred Return, we sit down with Craig Wortmann, Founder of Sales Engine, 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/
  

  Connect with Craig Wortmann💡 LInkedIn: 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.

In this episode of Preferred Return, we’re joined by Lauren Schirle, Senior Manager - Strategic Initiatives at VIRIDIS Fund Solutions, 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/
  
  Connect with Lauren Schirle💡 LINKEDIN: https://www.linkedin.com/in/lauren-schirle/ 

In this episode of Preferred Return, we sit down with Usamah Khan, Vice President of Data & Technology at White Star Capital, 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:

In this episode of Preferred Return, we sit down withJack Boudreau, Co-Founder & CEO ofHabits, 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/

  
  

  Connect with Jack Boudreau

  💡 LINKEDIN:https://www.linkedin.com/in/jack--boudreau/ 

In this episode of Preferred Return, we sit down with Altvia’s very own Head of Engineering, Jef Rice, to explore the evolving world of data strategy and its impact on the alternative investment industry.

Jef shares how engineering teams and tech providers are helping to shape innovative, scalable solutions for firms to win in private capital markets. Jef dives into the power of data lakes, the importance of experimentation, and how de-codifying your data can transform the LP experience.

In this episode, you’ll learn:

Things to listen for:

(00:00) Introduction to Jef Rice

(01:55) Jef’s background: From startups to Altvia

(03:48) Startup vibes at Altvia: Moving fast and staying innovative

(05:53) Rapid experimentation and customer-focused data strategies

(07:53) The phase of technology: AI’s role in rapid innovation

(10:00) Harnessing data to inform decisions and democratize innovation

(12:41) Jef’s approach: Saying yes, experimenting, and enabling teams

(14:33) Lessons from ZipRecruiter: Data-driven tools for impact

(17:00) Defining a data strategy: Turning data into a strategic asset

(18:54) Data lakes vs. data warehouses: Flexibility vs. structure

(22:22) Data lakes as enablers of discovery and experimentation

(26:20) Data lakes’ modularity and ability to scale innovation

(29:31) The role of AI: Context and the importance of a strong data foundation

(32:10) Connecting internal and external data for customer impact

(35:05) Data’s role in creating better customer experiences

(40:40) Jef’s vision for making data strategy accessible and impactful

Resources:

"AI and data quality are coming into play. AI isn't going to be any good if your data's rubbish. And data quality has always been a big issue on Salesforce." - Ben McCarthy, Founder of Salesforce Ben

In this episode of Preferred Return, we hear from Ben McCarthy, also known as Salesforce Ben, about the journey of building Salesforce Ben into the leading media company within the Salesforce ecosystem. Ben shares how his passion for Salesforce and creating content turned into a thriving business, now celebrating 10 years and a team of 23. Ben explores the evolution of the Salesforce platform, the role of AI, and the need for niche expertise in consulting.

In this episode, you’ll learn:

Things to listen for:

(00:00) Introduction

(01:18) Welcoming Ben McCarthy, the story behind Salesforce Ben

(04:05) Early days of Salesforce Ben and initial traction

(07:10) Transition from blog to a full media company

(10:32) Ben’s early encounters with Salesforce and his initial experiences

(13:52) How the Salesforce ecosystem has evolved over the years

(16:24) Exploring Salesforce’s approach to multi-cloud and acquisitions

(19:45) Ben’s take on Salesforce’s AI advancements

(22:37) The importance of quality data for AI effectiveness

(25:03) The unique flexibility and customization of Salesforce

(28:10) Common challenges in Salesforce implementations

(31:19) The role of Salesforce’s ecosystem and niche solutions

(35:22) Discussing Salesforce’s new features like Data Cloud

(38:47) How industry experience impacts Salesforce consulting success

(41:15) The evolution and future of specialized Salesforce solutions

(44:03) Final thoughts on the growth and future of Salesforce

Resources:

Connect with Ben McCarthy🐦 X: https://x.com/salesforceben💡 LINKEDIN: https://www.linkedin.com/in/salesforceben/

"We grow apples and sell to apple buyers—don’t waste time convincing orange buyers."  - Gui Costin, Founder & CEO of Dakota.

In this episode of Preferred Return, we revisit former host Jeff Williams’ conversation with Gui Costin, Founder and CEO of Dakota. Together, they explore the art of capital raising and how Dakota became a leading data platform for investment firms. Gui dives into Dakota's journey, the importance of consistency in sales, and why building a transparent, high-performance culture matters as much (if not more) now as it did when this conversation was originally recorded. Gui also shares the story behind the creation of Dakota Live, their unique content-driven sales tool, and how it revolutionized capital raising.

In this episode, you’ll learn:

Things to listen for:

(00:00) Introduction to Gui Costin

(01:05) Gui's background and how Dakota was founded

(04:17) The challenges of fundraising in today’s market

(06:52) The philosophy behind "every day is a great day to sell"

(09:34) Core principles: Building a culture of transparency and accountability

(11:47) The creation of Dakota Live and its impact on capital raising

(15:10) "We grow apples and sell to apple buyers" – avoiding the convincing game

(17:45) The role of consistency in successful sales

(20:12) How Dakota's culture of kindness drives high performance

(23:03) Understanding the importance of knowing your buyer

(25:35) Gui’s perspective on the future of investment sales and tech

(28:48) Collaborating with teams to maximize effectiveness

(32:01) Final thoughts on culture, consistency, and scaling

Resources:

Learn more about Dakota: https://www.dakota.com/

Connect with Jeff: https://www.linkedin.com/in/jeffwms/

More from Altvia: https://altvia.com/

Connect with Gui Costin

X: https://x.com/guicostin

LinkedIn: https://www.linkedin.com/in/guicostin/

In this episode, we sit down with Coloradan, Duncan Mendelsohn, the founder of Goodseed Capital, to explore his fascinating career journey from mortgage banking in NYC to launching a cannabis-focused real estate investment and advisory firm in Colorado. Duncan shares his insights on the evolving cannabis industry, the "Green Rush" era, and how Goodseed Capital offers a unique, low-risk, high-yield investment opportunity in this space. Tune in to learn how strategic structuring and a deep understanding of real estate and cannabis are driving Goodseed's success in a rapidly changing market.

Join Ray Grant, VP of Client Success at Altvia, and Don Stewart, Chief Financial Officer at Spire Capital, for an insightful conversation. Don shares his illustrious journey as a c-suite executive, his impactful tenure at Spire since 2006, and Spire's proactive tech and compliance-first mindset.

In this engaging discussion, Don sheds light on Spire's strategic investments, highlighting their innovative approach to leveraging technology for continued success. Ray and Don also explore Spire's approach around transparency and responsiveness to investor queries, which differentiates their ability to develop best-in-class relationships. Gain exclusive insights into Spire's future plans, including their collaboration with Altvia for an upcoming fundraise.