*]:pointer-events-auto scroll-mt-(--header-height)" dir="auto" tabindex="-1" data-turn-id= "b1254d76-9782-4038-9aa8-382a2395255e" data-testid= "conversation-turn-13" data-scroll-anchor="false" data-turn="user"> *]:pointer-events-auto scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" tabindex="-1" data-turn-id= "80196f3d-a0ce-44b9-917e-9b4df5d25b93" data-testid= "conversation-turn-14" data-scroll-anchor="true" data-turn= "assistant">

Why do small business leaders keep buying more software yet still feel like they are drowning in logins, dashboards, and unfinished work?

In this episode of Tech Talks Daily, I sit down with Jesse Lipson, founder and CEO of Levitate, to unpack a frustration I hear from business owners almost daily. After years of being pitched yet another tool, many leaders now spend hours each week troubleshooting software instead of serving customers. Jesse brings a grounded perspective shaped by decades of building SaaS companies, including bootstrapping ShareFile before its acquisition by Citrix, and what stood out to me immediately was how clearly he articulates where the current software model has broken down for small businesses.

We talk about why adding more apps has not translated into better outcomes, especially for teams without dedicated specialists in marketing, finance, or sales. Jesse explains how traditional software often solves only part of the problem, leaving owners to become accidental experts in accounting, marketing strategy, or customer communications just to make the tools usable. From there, our conversation shifts toward what he believes will actually matter as AI adoption matures. Rather than chasing full automation or shiny new dashboards, Jesse argues that the real opportunity lies in blending intelligence with human guidance, allowing AI to work quietly behind the scenes while people remain the face of authentic relationships.

A big part of our discussion centers on trust and connection in an AI-saturated world. Jesse shares why customers have become incredibly good at spotting automated communication and why relationship-based businesses cannot afford to lose the human element. We explore how AI can act as a second brain, helping business owners remember details, follow up at the right moments, and show up more thoughtfully, without crossing the line into impersonal automation that turns customers away. His examples, from marketing emails to customer support, make it clear that technology should support better relationships rather than replace them.

We also look ahead to what small businesses should realistically focus on as AI evolves. Jesse offers practical guidance on getting started, from everyday use of conversational AI, to building internal documentation that allows systems to work more effectively, and eventually moving toward agent-based workflows that can take on real operational tasks. Throughout the conversation, he keeps returning to the same idea, that AI works best when it helps people become the kind of business leaders they already want to be, more present, more consistent, and more human.

If you are a founder, operator, or small business leader feeling overwhelmed by tools that promise productivity but deliver friction, this episode offers a refreshing reset. As AI becomes more capable and more embedded in daily work, the real question is not how many systems you deploy, but whether they help you build stronger, more genuine relationships, so how are you choosing to use AI to support the human side of your business rather than bury it?

Useful Links

• Connect with Jesse Lipson
• Connect with Jesse on X
• Learn more about Levitate