Why Athletes Aren’t Bad With Money

Athletes get told they’re bad with money. Elijah Blomquist, Bespoke’s first employee, says that story misses the point. In this episode of the Bespoke Audio Collection, Claire Martin talks with Elijah about financial planning for professional athletes and why leading with “education” talks down to people who often came out of top programs on full scholarships. What athletes are usually short on is time, and an advisor who is transparent and lets them own the decisions.

What Does Financial Planning for Professional Athletes Involve?

Privacy and asset protection, and why how you title what you own matters

• Jock tax: what changes when you play in multiple states
• Managing the circle of managers, agents, and advisors that keeps growing
• Why athletes should have room to back their own convictions
• Why athletes get sold the pipe dream more than almost anyone
• What athletes and first-generation entrepreneurs have in common

What Should Athletes Ask After Any Financial Pitch? Elijah leaves listeners with one question: what’s the worst-case scenario, and how are you built to withstand it?

About the Guest Elijah Blomquist is Bespoke’s first employee and works with professional athletes on wealth planning.

Go Deeper Read Elijah’s article, Wealth After the Win: Financial Strategies for Professional Athletes.

This episode is for founders who have built extraordinary value in a single generation, and for inheritors navigating the responsibility of wealth passed down to them. Host Claire Martin sits down with Nicole Taylor, President and CEO of Silicon Valley Community Foundation, to explore why more donors are choosing a community foundation over building their own private foundation and what that choice actually looks like in practice. Nicole breaks down the real difference between the two models, why donor advised funds are far more active than most people assume, and how SVCF helps donors convert complex assets — pre-IPO stock, crypto, real estate, LP interests — into charitable impact without standing up a private foundation or family office from scratch. The conversation also covers how the next generation of founders is choosing to build purpose and business at the same time, and where AI is genuinely helping (and still struggling to help) under-resourced nonprofits. Walk away with a clearer way of thinking about stewardship, one that looks at your full financial picture, not just your giving budget.

Preparing for a Liquidity Event: How Family Businesses Can Plan for a Sale, Recapitalization, or IPO

This episode is for founders and family business owners preparing for a liquidity event — a sale, recapitalization, or IPO that turns years of work into a new chapter for the family.

Co-hosts Claire Martin and Matt McClintock are joined by Brendan Bybee and S. Craig Stone II, managing partners at Stone Bybee & Associates, who bring over 30 years of combined experience helping families navigate exactly this transition.

In this episode:

• How to start preparing for a liquidity event years before a transaction
• Why treating succession as an ongoing process — not a single event — builds a stronger next generation
• How families can stay ready for whatever comes after the deal closes
• A “fire drill” exercise Brendan and Craig use to help families build real continuity
• Why preserving options early gives families more strength and flexibility down the road

Walk away with a clearer sense of how starting these conversations early, even when they’re hard, helps families build resilience and confidence for the road ahead.

This episode is for attorneys, CPAs, and other professionals whose affluent clients are asking about Bitcoin. Host Claire Martin sits down with Matt McClintock, Founder and CEO of Bespoke Group, to unpack why Bitcoin requires a different conversation than the broader cryptocurrency market and what the mainstream is covering.

Matt traces Bitcoin’s origin back to Satoshi Nakamoto’s 2008 white paper, explaining how its fixed 21 million supply and built in halving mechanism set it apart from tokens that were pre-mined and controlled by their founders. The conversation covers the mindset differences between long-term Bitcoin holders and crypto investors, how professionals can screen for illicit activity using chain analytics, and why self-sovereignty often gives way to trust and entity structures once clients want tax mitigation or reliable wealth transfer.

Walk away with a clearer framework for advising clients who hold digital assets.

Go deeper with the Matt’s whitepaper “The Sovereignty Paradox here.

“Estate planning for a business is not just about the sale. It is about the person, the family and what they actually want their work to mean.”

Most owners frame it as a simple financial question: keep the business or sell and move on. In reality, that decision sits on top of founder identity, the next generation’s appetite for stewardship and hard conversations that have been delayed for years. In this episode, Founder and CEO Matt McClintock and BHR Law Group Founder and Managing Partner Blaine Burch digs into those hidden drivers and shows how naming the different entrepreneurial styles in a family can turn succession from a last minute deal mechanic into a plan that actually reflects the people, culture and company involved.

“We are not living through the end of the world. We are living through a transition from one global order to another, and that is uncomfortable.”

Geopolitics can feel like an endless scroll of crises, but our Strategic Partner and Geopolitical Advisor Jacob Shapiro focuses on what actually matters for investors: using geopolitics as a method to understand how states behave and to decide where you and your capital should be over the next decade, not the next quarter. This conversation explores why our brains overreact to bad news, how today’s disorder fits into a longer pattern of shifting eras, and why Jacob centers his work with families on three forces that will shape the next ten to fifteen years: the move from a US dominated world to a more multipolar one, a major energy transition, and a new wave of technological change across the real economy.

“It used to feel like James Bond or Jason Bourne with a suitcase of passports. Now it is just how serious families manage risk.”

Residency and citizenship by investment have moved from the fringe to the main table for wealthy families who want options if the world keeps shifting. In this episode, Henley Group’s Judi Galst and Bespoke’s Sune Hojgaard-Sorensen unpack how “plan B, C, and D” really work in practice for global families, and how those choices intersect with structures, tax residency and long term family strategy. They explore why demand for alternative residency exploded after 2020, the practical differences between residency and citizenship, and how to think about these tools as part of an integrated operating system rather than a one‑off passport purchase.

“We are no longer talking about theoretical adoption. Clients already have significant wealth in these assets, and it has to be integrated into real planning frameworks.”

Bitcoin and other digital assets are no longer outside the system. As bearer assets, they require clear custody, control, and title or even well designed structures fail. Our Founder and CEO Matt McClintock and Kyle Lawrence, Partner in the Corporate and Securities Practice Group at FRB, walk through how familiar frameworks like trusts and LLCs extend to digital assets, where they break down, and how to structure them correctly. You will hear why custody is the central challenge, how lost access continues to erase billions in wealth, and why assigning assets on paper is not enough. This episode clarifies how to say yes, avoid common mistakes, and bring digital assets into a fully integrated plan.

“We’re at a historic inflection point. Wealth is changing hands at a level we’ve never seen before, into the hands of new decision makers with a broader view of what their wealth is for.”

Building on our episode about Bitcoin custody and wealth planning, this conversation shifts from mechanics to people: modern wealth holders and the practitioners who serve them. Co-Founder and CEO Matt McClintock and President of Client Services and Asset Management Sune Hojgaard-Sorensen to explore a historic wealth transfer, the rise of new decision makers, and how Bespoke’s “how to own, where to own, what to own, and why” framework supports a more values-driven approach to stewardship.

“For years, when someone walked in with significant Bitcoin wealth, the answer was simply no. Now there is no regulatory argument left for saying you can’t engage with this.”

Bitcoin has moved from speculative trade to concentrated family wealth, creating new pressure on estate planners, trustees, and fiduciaries. Founder and CEO Matt McClintock and Tetra CEO Didier Lavallée discuss how to bring a digital bearer asset into established legal and custody frameworks, so practitioners can use familiar strategies instead of reinventing the playbook. You will hear why the default answer was “no” for so long, what has changed in the regulatory and custody landscape, and how values-driven Bitcoin families are using this wealth to build the world they believe ought to exist.