In this episode of Crazy Wisdom Podcast, Stewart Alsop is joined by Jenna Biancavilla, a multi-entrepreneur and founder in financial services and tech. They discuss Jenna’s experience navigating complex regulatory landscapes in finance, her insights into global work dynamics, and her unique approach to asset management for business owners and families. Stewart and Jenna also cover the challenges of building a tech platform from the ground up, exploring cultural and logistical hurdles along the way. You can check out Jenna’s latest venture at BeSvvy.com where she connects clients with trusted advisors.

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Timestamps

00:00 Introduction to the Crazy Wisdom Podcast

01:21 Navigating Financial Regulations and Borders

02:56 The Complexities of State and Federal Regulations

07:45 Philosophical Insights on Business and Identity

12:53 The Role of Technology in Financial Services

19:17 Building a Trustworthy Financial Platform

26:14 Exploring New Technologies in Financial Planning

27:58 Remote Work in a Regulated Industry

29:17 Excitement for Future Business Growth

31:52 Valuing and Scaling Businesses

33:16 Challenges of Building a Technology Company

41:26 Cross-Border Financial Advising

44:20 Cryptocurrency and Regulatory Risks

49:17 Future Plans and Market Expansion

Key Insights

1. Navigating Regulation as a Financial Advisor: Jenna explains the layers of regulatory complexity that financial advisors face, especially those operating across state and national borders. Being SEC-registered allows her firm to operate more freely within the U.S., but international borders introduce significant restrictions. These regulations are in place to protect clients but can also make the advisor’s job challenging, as they need to register each office location where they meet clients, which complicates the lives of both advisors and clients in a globally mobile world.
2. The Rise of Digital Nomadism and Its Challenges in Finance: Stewart and Jenna discuss the impact of digital nomadism and remote work, particularly on regulated industries like financial services. Jenna shares that many business owners and wealthy clients are interested in moving states or even countries to optimize taxes and enjoy greater mobility, but that this lifestyle doesn’t always align well with the rigid regulatory framework that advisors have to navigate.
3. The Emotional Side of Exit Planning: Jenna describes the psychological transition many business owners face when preparing to exit their companies. For many, their business is intertwined with their identity, and letting go can lead to self-sabotage if not handled well. To support clients through this, Jenna often brings in life coaches and therapists, emphasizing that financial planning is often also about personal and emotional alignment, not just numbers.
4. Embracing Technology and AI in Finance, Carefully: While Jenna uses technology extensively in her businesses, she remains cautious, particularly in the finance arm, where accuracy is paramount. In her view, the promise of robo-advisors and AI in financial planning has not yet replaced the need for human intuition and oversight, although AI is helpful in client communication training for new advisors and for content creation in marketing.
5. Building a Tech Platform for Trustworthy Financial Advice: Jenna’s second business, BeSvvy.com, is a tech platform designed to help clients find trustworthy advisors. The platform uses a blend of algorithms and human vetting to ensure advisors are not only certified but aligned with clients’ best interests. Jenna’s approach contrasts with relying solely on regulatory safeguards, aiming to disrupt the industry by using technology to put consumer needs first.
6. Cultural and Logistical Challenges of Outsourced Development: Jenna shares her experience outsourcing early development work to India for cost efficiency but found that cultural misunderstandings and a lack of alignment in vision became barriers. This experience taught her the importance of communication and trust in development partnerships. For version two of BeSvvy.com, Jenna has moved development to a U.S.-based team, allowing for more direct oversight and fewer cultural barriers.
7. A Pragmatic Approach to Scaling a Technology Business: Jenna has opted for a measured, profitable approach to scaling BeSvvy.com, rather than pursuing rapid, venture-funded expansion. Recognizing the challenges of building a marketplace, she sees slow, steady growth as the best way to balance quality with business sustainability, contrasting with the traditional “burn rate” model of many tech startups.