In this episode of Wholly Fractional, we sit down with Mark Jackson, co-founder of BeSolo, to explore the challenges and opportunities facing solopreneurs, freelancers, and fractional professionals. Mark shares his insights on health benefits, taxes, retirement savings, and business operations—key pain points for anyone working independently.
We dive into the golden handcuffs of health insurance, the explosion of the freelance economy, and how BeSolo is revolutionizing operational support for independent workers. Whether you're a seasoned fractional pro or just getting started, this episode is packed with actionable strategies to help you set up and run your business more efficiently—without sacrificing stability.
🎧 Tune in for:✔️ How BeSolo is solving the benefits and compliance problem for solopreneurs
✔️ The rapid rise of fractional work and why it's here to stay
✔️ Avoiding tax pitfalls: What solopreneurs must know about estimated taxes
✔️ The difference between an LLC and an S-Corp (and which is right for you)
✔️ Why 50% of independents rely on a spouse’s health insurance—and what to do instead
✔️ Mark’s top tools and strategies for thriving as a solopreneur
🔗 Resources & Links:
Visit BeSolo.io to learn more about how their platform can support your journey as a fractional professional.
Find Mark Jackson on LinkedIn
Episode Chapters & Timestamps
[00:00] Introduction & the rise of fractional work
[02:30] Mark’s background & the journey to founding BeSolo
[05:45] The healthcare struggle for solopreneurs & why benefits are broken
[08:00] The PEO solution & how it simplifies independent work
[12:15] The explosion of freelance work since 2020
[16:00] Common mistakes solopreneurs make when transitioning from W2
[20:30] LLC vs. S-Corp: Choosing the right business structure
[24:45] How BeSolo removes admin & tax burdens for solopreneurs
[29:00] Retirement planning for independent workers
[34:00] Lightning Round: Mark’s favorite tools, books, and career insights
Key Action Items for Listeners:
✔️ Evaluate your business structure – Is an LLC or S-Corp better for your situation?
✔️ Plan for tax obligations – Don’t get blindsided by quarterly estimated taxes.
✔️ Explore healthcare options – Don’t assume you have to rely on a spouse’s benefits.
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