Jess Lipson, founder and CEO of Levitate, joins host Scot Wingo for a focused, framework-driven conversation on how SaaS founders should think about their businesses in the age of AI. Jess has been building SaaS since before the category had a name. His first company, ShareFile, sold to Citrix and eventually became a billion-dollar business. At Citrix, he ran the company's entire SaaS portfolio. Now at Levitate, a relationship marketing platform serving nearly 9,000 small businesses, he's spent the last year working out a clear-eyed answer to one of the most common questions Scot hears from Triangle founders: what do you actually do about the SaaSpocalypse? In this episode, Jess introduces two tests every SaaS founder should run: the Removal Test (if you strip AI out of your product, does it still function?) and the Growth Re-acceleration Test (is your growth rate going up or down, and what does that signal to investors?). Scot adds a third indicator from what he's seeing across the Tweener Fund portfolio: churn driven by customers who are now vibe-coding their own replacements. Together, they walk through how the buy-vs.-build equation has shifted 10 to 100 times, why having AI features is now table stakes rather than a competitive advantage, and what it looks like to build a business where new frontier model releases feel like tailwinds instead of threats.

Timestamps
00:00 Cold Open & Welcome

00:29 Sponsors: Robinson Bradshaw & Bank of America

01:24 Scot's Intro: The SaaSpocalypse

02:31 The February Tweener Times Piece

03:05 Why This Episode Exists

04:08 Welcome Jess Lipson

04:37 How Scot & Jess Know Each Other

05:10 Jess's SaaS Pedigree: ShareFile to Citrix

05:49 SaaS Multiples Have Collapsed

07:00 Salesforce, HubSpot & Workday Are Down Too

08:13 AI Features Are Table Stakes

09:50 Is This the Lowest SaaS Multiples Ever?

11:28 Investment Landscape: Subscale SaaS Is Struggling

12:23 Framework #1: The Removal Test

14:22 Framework #2: Growth Re-Acceleration

15:23 Scot's Third Signal: Vibe Coding Churn

17:32 The Buy-vs.-Build Equation Has Shifted 10–100X

19:29 When Claude Becomes Your "Single Pane of Glass"

19:44 MCP Servers & Levitate's API Revamp

21:50 How Levitate Is Passing Its Own Tests

22:31 New Offering: Helping SMBs Actually Implement AI

23:44 Software + Services as the Durable Model

24:11 The Fear Index: Do You Dread New AI Releases?

24:50 Raleigh Founded & Closing Thanks

25:04 Outro

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Where to Find Jesse Lipson:
LinkedIn: https://www.linkedin.com/in/jesse-lipson-625195/
Levitate Ai: https://www.levitate.ai/

Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo

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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West.

We couldn’t share posts like this without our amazing sponsors:

Platinum:
NC IDEA: https://ncidea.org

Gold Sponsors:
- Balentine: https://www.balentine.com/triangle-entrepreneurs
- EisnerAmpner: https://www.eisneramper.com
- Robinson Bradshaw: https://www.robinsonbradshaw.com

Silver Sponsors:
- Automated Consulting Group: https://automated.co
- Bank of America: https://business.bofa.com/en-us/content/technology-industry-group.html

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/