Mark Jackson, co-founder and CEO of Besolo, joins Bradley Jacobs to discuss the operational challenges facing fractional executives and independent consultants. Mark shares his journey from fractional CRO to building Besolo, a comprehensive back-office solution for solopreneurs. The conversation explores the critical infrastructure decisions every business-of-one must make, including entity structure (LLC vs S-Corp), tax compliance, healthcare access, and benefits planning. Mark reveals how his wife's kidney transplant exposed the healthcare gaps for independent professionals, inspiring him to create a solution that pools solopreneurs together for group benefits access. The discussion covers productizing services for sustainability, avoiding the common trap of churning back to W-2 employment, and the essential playbooks every fractional executive needs. Mark emphasizes that 90-95% of solopreneurs live in fear of compliance issues and explains how proper structure and support can eliminate these concerns while maintaining the freedom that draws people to fractional work.
Learn More:
Scale your fractional practice: https://mylance.co
Connect with Bradley Jacobs: https://www.linkedin.com/in/bradley-r-jacobs/
Connect with Mark Jackson: https://www.linkedin.com/in/jaxnmarx/
Check out Besolo: https://www.besolo.io
00:00 Welcome and guest introduction
00:43 Mark's journey from fractional CRO to Besolo
05:21 Understanding S-Corp tax benefits
07:30 The full-fledged business challenge
11:14 Bradley's solopreneur structure struggles
14:46 Why fractionals return to W-2 employment
19:41 Productizing services for sustainability
22:36 Essential business infrastructure stack
25:20 Recording restart after technical issues
26:15 LLC vs S-Corp decision framework
32:35 Legal risk vs taxation considerations
33:42 Complete solopreneur toolkit overview
39:19 Retirement planning for solo businesses
41:32 Besolo's comprehensive solution approach
43:43 Ideal customer profile and timing
46:39 Final advice for overwhelmed solopreneurs