About
About a year into starting AirBnb, Brian Chesky’s life was in ruins. He had been eating very little, everything he and his cofounders tried simply wasn’t working, and morale was running thin.Then the Great Financial Crisis of 2008 hit.
“Winter is coming” his mentor Paul Graham said, which, after the worst year of his life, really stung Brian’s soul. “But you will be OK,” Paul said, “We need founders who've got survivor instinct and won't die. We want cockroaches, and you are cockroaches. You will not die. You're selling cereal boxes, for God's sake.””And that was the greatest compliment anyone had given me at the time,” Brian recalls.
You see, that’s me. I’m a cockroach.Growing up as the third of four boys, I needed to find ways to survive and compete.
On my middle school basketball team, my Athletic Director nicknamed me The Badger for my willingness to full court press in the first half and harass the other team. To this day, when I play with players a decade or more younger than me, the first thing I often hear from my opponent I match up with is “Oh fuck, not you again.”Tenacity and resourcefulness became my biggest strengths.Whether it was recruiting for an investment banking position, starting an E-Commerce business in college, or searching for solutions to my brother’s terminal cancer prognosis, every time I had a goal that I didn’t think I could reach, I asked myself one question:“What am I going to do differently to be successful here?”Because I realized that an average effort with an average strategy leads to an average outcome and ultimately an average life.I've come to realize this mindset isn't for everyone. But for me, I can't imagine living any other way.Welcome to my site. Stay awhile, and please don’t hesitate to reach out.
© 2026 JonHegarty.com. All Rights Reserved.
Tax Strategist
I work alongside your CPA to uncover overlooked tax-saving opportunities and implement strategies designed to reduce your tax burden.
How it works:
Review your returns: Send me your CPA-prepared tax returns and supporting documents. We review your filings, identify potential opportunities, and prepare questions specific to your situation.
Identify Opportunities: Meet with me to discuss your goals, business structure, income sources, investments, and opportunities we identified.
Deliver Your Tax Strategy Report: Receive a detailed report outlining potential tax savings, implementation steps, estimated dollar impact, and coordination items for your CPA.
The initial review is free. You only pay if I identify meaningful tax savings.
Pricing Model:
| Category | Fee | Comment |
|---|---|---|
| One-time savings | 30% of savings | Savings identified and captured in the current tax year that are not expected to repeat. |
| Annual ongoing savings | 30% of first two years of realized savings | Strategies that create ongoing annual tax benefits. |
| Future savings | 10% of future value saved | Strategies requiring future implementation, restructuring, or planning. |
Some examples of clients who are often leaving money on the table include:
A business owner who has never optimized their entity structure.
A real estate investor who has not utilized available depreciation strategies.
A company owner who has not implemented advanced retirement plans.
A family that has not coordinated income timing, charitable giving, and estate planning strategies.
A crypto investor sitting on large gains seeking a way to minimize taxes upon realization
I do not replace your CPA and I do not prepare tax returns. I work alongside your existing advisors to identify opportunities and help ensure they are properly implemented.
© 2026 JonHegarty.com. All Rights Reserved.
Tax & Bitcoin-Aware Wealth Management
Wealth Management for People Who Want to Be Rich Someday
At some point, someone be honest with you that inflation is eating away at your purchasing power.Most wealth managers will tell you about diversification – or as Peter Lynch and I call it - diworsification. They will help you “play it safe” which in today’s world translates to "assured lackluster results.”Now, let me be clear. I don’t want you to take risks you can’t stomach. Investments should be prudent.
Use Bitcoin as an example. It represents an amazing investment opportunity with asymmetric upside. Over any reasonably long period, it has only soared in value. Sure - volatility comes with the territory, but it should have a place in any wise portfolio. Whether your allocation is 3% or 50%, that is your decision, but it is clear that the path to long-term wealth is to make sizable allocations to investments with asymmetric upside.This sentiment is not controversial, yet astonishingly, you won’t hear it from most wealth managers!
Beyond making solid, concentrated selections, I aim to keep expenses low, minimize taxes, trade infrequently and own high quality assets. Not rocket science!
© 2026 JonHegarty.com. All Rights Reserved.
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Chasing a Ridiculous Goal
At age 32, I set an absurd goal:Become the #1 pickleball player in the world.I wasn't a collegiate tennis player.I wasn't a professional athlete.In fact, I was the seventh-best player on my DIII Massachusetts high school tennis team. That was 14 years ago.The mission isn't just about pickleball.It's about testing the limits of what is possible and encouraging others to pursue goals that appear unreasonable.Do you believe it’s never too late?
© 2026 JonHegarty.com. All Rights Reserved.
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Bitcoin Deferred Compensation Program
What if an employer could create life-changing wealth for employees without permanently giving away equity?
A Bitcoin Deferred Compensation Program allows employers to reward key employees with a long-term incentive tied to the performance of Bitcoin, encouraging retention, loyalty, wealth creation, and financial discipline.
Instead of paying an entire annual bonus in cash, an employer can allocate a portion of the bonus to a long-term Bitcoin incentive plan that vests and pays out in the future.
Our programs are designed to align the interests of the company and the employee while maximizing tax efficiency.
Benefits to Employers
Retain Key Employees
Long-Term Alignment
Self-Funding (with BTC appreciation)
Differentiate Your Compensation Package
Encourage Financial Discipline
Benefits to Employees
Participate in Bitcoin's Long-Term Appreciation
Potential Tax Advantages (LTCG treatment)
Build Meaningful Wealth
Alignment With Company Success
Exciting and Memorable Benefit
Who Is This For?
Family-owned businesses
Professional service firms
Small and medium sized businesses
Businesses with key employees they cannot afford to lose
Owners seeking alternatives to traditional cash bonuses or equity grants
Example:
Employer contributes $10,000 on an employee’s behalf.
Bitcoin appreciates 4x over five years.
Employer receives its original $10,000 back.
Employee receives $30,000 of appreciation.
Potential taxation: employer experiences no tax implication and receives the principle. The employee receives long-term capital gains treatment rather than ordinary income (subject to the specific structure and applicable law).
© 2026 JonHegarty.com. All Rights Reserved.
Our Story
In 2020, I was working in private equity in New York City when my younger brother Christian received devastating news: his osteosarcoma had returned.“When Osteosarcoma comes back the second time, we are much more limited in our options,” Christian’s oncologist told him. “It tends to be twice as aggressive and treatment is half as effective.”
Christian’s team recommended he enter the Clinical Trial system. Even then, most of the active trials were for drugs that his oncologist had known well and used for many years, yet she still showed little enthusiasm. The various trial options combined drugs named Sorafinib and Regorafinib, known as multikinese inhibitors, with drugs Christian had already received previously like Ifosomide and Etoposide. His oncology team were very familiar with these treatments and showed little enthusiasm given Christian's advanced stage.Looking back, Christian described the situation this way: “These were useful treatments, they said–just not likely to be effective once I reached my stage. Perhaps the multi-kinese inhibitors could extend my life a bit.’”That’s when I recommended we go “all in” on integrative and holistic health. As someone who has always approached problems analytically, I found the calculus surprisingly simple: Christian was running out of conventional options. If the standard path was unlikely to work, we had to seriously explore alternatives. We had to believe there might be another way forward, and then dedicate ourselves to finding it.It sounds bizarre to say, but I actually felt a sense of relief when Christian’s doctors finally said that his chance of achieving long-term remission was ‘basically zero’ with the Clinical Trial options we were considering. It made the decision-making easy. We weren’t going to employ a well-researched strategy that was sure to fail. Now, at the very least, we knew exactly where to spend our time.We spent the next year researching, implementing, and trying to find a solution. Christian and I were living together in a small two bedroom apartment with no dishwasher–and suddenly in our kitchen, we had an infrared sauna, a hyperbaric oxygen chamber and a bunch of dirty dishes.Christian settled on a bold decision. As he remembers it, “I told my oncologist I wasn’t ready to enter a Clinical Trial, that I needed a period of time to get my head on straight and also to see how quickly the cancer was growing. She agreed to give me 5 weeks – nothing more. And in the 5 weeks, I wanted to do as much as I could for my health.”We made sure we considered everything. We had to make sure we left no stone unturned. We listened to everybody that had an opinion in addition to our own dedicated research. We had no idea how much of an impact our interventions would have, but we had this sense that it could be one or two, maybe three, of these less-well-known therapies that, taken together, might be enough to move the needle in a positive direction.Christian ended up turning down the trial and continuing to seek and implement alternative strategies. Our big break came in October 2021 just over a year after Christian’s recurrence. I had reached out to the Burdo family, whose son Alex was Christian’s age and was 6 years in remission from an equally difficult case of the same cancer. He had worked with a naturopath Dr. Bricca who administered a compelling copper chelation strategy.In Christian’s words: “Basically, the idea we learned from Alex was that according to one naturopathic theory, tumors need copper to form initially. If one can lower their copper to a level below the standard range but above a critical level, they could prevent a recurrence without side effects. Of course, we had no idea if this would be true for me, but it seemed to be working for him and we were excited to finally have found someone with a potential solution to our problem.”For us, that was the breakthrough we needed. Osteosarcoma is one of the most difficult cancers to treat. There was nothing more valuable than finding someone who had overcome the challenge we were facing.As of this writing in Q3 2026, Christian remains in remission from his cancer. While he continues to deal with leg-related complications from previous surgeries, his cancer has not recurred since his August 2021 surgery and he continues his prescription of the copper-chelation drug. He continues to live a normal life.We are not medical providers and do not provide medical advice. The above represents Christian’s particular story. We encourage patients to make informed choices, listen to their doctors, and get multiple opinions. We created GoingWell, a 501(c)3 nonprofit to help patients research various options and advocate for themselves alongside their medical team.
The Christian Hegarty Initiative by GoingWell
After Christian's battle with recurrent osteosarcoma, I became deeply passionate about helping patients and families navigate difficult diagnoses and explore every reasonable avenue available to them.I now provide free support to a small number of families who feel aligned with this mission.Because we hope these experiences may help future patients, I strongly prefer to work with individuals who are open to documenting their journey and sharing lessons learned with others at a later date.Our goal is simple: to help families feel informed, empowered, and confident that no stone has been left unturned.If you or someone you know is facing a difficult cancer or chronic disease and is interested in our advocacy work, please reach out to [email protected]. Please include answers to the following questions:Context - About you, your family, your interests, career and hobbies
Diagnosis
Current stage
What are you hoping to accomplish?
What most excites you about our help?
Are you open to documenting your journey with written, audio and/or video updates? We will never share your information publicly without your consent.
© 2026 JonHegarty.com. All Rights Reserved.
Private Equity
We invest in exceptional small and middle-market businesses.
We consider both minority and controlling investments in companies generating approximately $800,000 to $10 million of annual earnings.
We are industry agnostic and seek businesses with:
Strong management teams
Durable competitive advantages
Recurring customer relationships
Opportunities for long-term value creation
While we evaluate opportunities across many industries, we have particular expertise in residential construction and related services businesses.
As operators, investors, and advisors, we understand that every business is unique. We strive to be flexible, move quickly, and structure transactions that work for founders, families, and management teams.
Whether you are considering a full sale, a partial liquidity event, a growth partnership, or a succession solution, we would welcome a conversation.
Preferred Transaction Types
Founder succession
Family-owned businesses
Minority investments
Recapitalizations
Special situations
We have a long investment horizon and prefer to think in decades, not quarters.
© 2026 JonHegarty.com. All Rights Reserved.