1:05:37

In this Raise Capital Legally podcast episode, host Krisha Young and attorney Kim Lisa Taylor interview Bob Bowman, creator of the Commercial Underwriter software platform. The conversation traces Bob’s path from selling office equipment and buying single‑family homes to becoming a multi‑asset commercial real‑estate investor, highlighting how a private‑money bootcamp and mentorship shaped his ability to raise capital. Bob explains why existing underwriting tools were inadequate, leading him to develop a cloud‑based, AI‑enhanced software that works across asset classes. He and the hosts discuss common underwriting errors—property‑tax miscalculations, payroll cuts without context, and reliance on unrealistic pro‑formas— and stress the importance of “common‑sense” underwriting. The dialogue also covers legal aspects of raising private money, deal structuring (preferred returns, promote, acquisition fees), partnership dynamics, and the risks of large management teams. Bob demonstrates the Commercial Underwriter dashboard, showing automated cash‑flow models, IRR and average annual return calculations, and how the tool streamlines investor reporting. The episode concludes with promotional details for a two‑day commercial underwriting class, pricing for the software subscription, a $500 discount for referrals through Kim, and ongoing free learning labs.

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