In this episode of Terminal Value, I'm joined by David Sosna, founder and CEO of Sympera AI, which raised a $10M seed round to bring agentic AI into relationship banking, to discuss why a copilot is the wrong model for enterprise AI, whether AI replaces relationship bankers or expands the market they serve, and why the real win is embedding AI into the banker's process instead of bolting on a chatbot.

We cover why relationship banking is a large, human, relationship-driven market, why more query and data tools never fixed the banker's day, how Sympera narrows a huge book down to a few fully-researched opportunities and tells the banker what to do next, how it blends public, purchased, and internal bank data without ever exposing what the bank holds, why betting on a single AI model is risky and how a multi-model stack with tuned tools answers it, why running everything through the most expensive frontier model doesn't scale, why banks that try to boil the ocean get nothing done, and why vertical AI's real edge is embedded judgment rather than a better chat box.

0:00 Hook: Why AI copilots fail without process redesign
0:45 Intro to David Sosna and Sympera AI
1:29 How relationship bankers grow and protect client relationships
4:04 Why CRM and data tools still depend on banker judgment
9:28 How Sympera narrows a market to five actionable opportunities
12:43 From bank priorities to ranked leads and next-best actions
16:39 Data security, lead accuracy, and continuous model validation
19:47 Feedback loops, inference cost, and scanning at scale
24:46 Why Sympera uses multiple models and keeps outreach human-reviewed
29:22 Bank targeting, pricing, and the work of changing user behavior
34:53 Salesforce, vertical AI, and the future banking agent stack
41:38 AI-native teams, banker productivity, and why copilots fall short
49:05 Closing takeaways

In this episode of Terminal Value, I'm joined by John Taylor Garner, founder and CEO of Odynn, an AI-native travel and loyalty infrastructure company that has raised over $9M in seed funding from Bonfire Ventures and Fiat Ventures, to discuss why points and miles behave less like a rewards program and more like a private economy, why the real product in travel is the decision layer rather than the booking, and how Odynn turns a multimillion-dollar embedded-travel build into something a late-seed startup can afford.

We cover how the fragmented travel rewards stack works today, why Expedia and Booking quietly control most of embedded travel, why points and miles only ever depreciate, how Odynn acts as a "Shopify for travel rewards" that compares dollars, points, and miles in one place, how the company prices and earns alongside its bank customers, what it takes to sell to banks as a young startup, and how an agentic AI concierge could turn travel from something you search into something you delegate.

0:00 Hook: Airlines don't make money flying planes

0:45 Intro to John Taylor Garner and Odynn

1:35 How the travel rewards stack works today

3:25 Banks, OTAs, and the Expedia/Booking duopoly

5:55 Where it breaks down for the consumer

8:10 Why points and miles only lose value

10:35 What Odynn is and how the product works

16:15 Pricing, commissions, and supply economics

20:30 Customers, competition, and the $60K disruption

25:00 Winning big banks and proving longevity

30:00 The AI concierge and the future of loyalty

36:00 Building AI-native: agents, engineers, and OpEx

41:55 Closing takeaways

In this episode of Terminal Value, I'm joined by Curt Aubley, co-founder and CEO of Sevii, and Stephen Collins, co-founder and CTO. Sevii is building autonomous defense and remediation for security operations, backed by Overline and BMW i Ventures. We discuss why the SOC was built for a slower world, what separates autonomous remediation from automated playbooks, and whether companies are culturally ready to let AI take real security actions.

We cover the legacy SOC workflow from alert to remediation and why it hands attackers a 15-minute head start, how Sevii's agentic "cyber warriors" go from detection to reported remediation in 2 to 15 minutes across the tools you already own, why per-asset licensing keeps security budgets predictable, Sevii's rule of only using AI where it's necessary, and why the hardest competition may be cultural trust rather than another vendor.

0:00 Hook: Why attackers get a 15-minute head start

0:40 Intro to Curt Aubley, Stephen Collins, and Sevii

1:26 How legacy SOC workflows reach remediation

4:35 Where speed, scale, and economics break the SOC

7:00 Why existing security tools still leave a bottleneck

9:29 What Sevii's autonomous remediation platform does

15:02 How Sevii moves from detection to remediation

19:31 How cyber warriors change SOC staffing

24:00 Customer control, MDR limits, and AI cost strategy

31:20 Sevii's ICP, buyer, and forward-deployed model

37:33 Asset-based pricing and predictable budgets

40:53 Competition, culture, and the future of autonomous defense

48:35 Closing takeaways

In this episode of Terminal Value, I'm joined by Tushar Makija, co-founder and CEO of Team Ohana, to discuss why headcount planning breaks the moment the CFO's model is locked, how AI agents are becoming the orchestration layer between HR and Finance, and why the real system of record should capture decisions, not just transactions.

We cover why a late hire is deferred capital, how a sales leader can plan ten hires from a single Slack prompt, why HR and Finance never demand better tools, human capital versus "agentic capital," and Tushar's "accelerate or die" case for moving now.

In this episode of Terminal Value, I'm joined by Manish Choudhary, co-founder and CEO of Flexprice, an open-source billing and metering platform for AI and API-first companies, to discuss why AI is breaking the old seat-based SaaS model, how pricing is shifting toward usage and outcomes, and why billing is starting to look less like admin software and more like core infrastructure.

We cover how software pricing evolved from one-time licenses to seats to usage, why billing becomes an infrastructure problem as companies move to consumption-based models, a real customer example that cut billing inquiries by 80% and surfaced hidden revenue leaks, how Flexprice lets finance teams change pricing without engineering work, and why open source may be a real wedge into the market.

In this episode of Terminal Value, I’m joined by Gentry Davies, co-founder and CEO of Crew, to discuss how consumer finance products shape behavior, why traditional budgeting tools often fail, and how Crew is building a calmer, more intentional alternative to today’s banking and investing apps.

We cover Crew’s pocket-based banking model, the problem with credit card and neobank incentives, how AI helps a small team move faster, and why Gentry ultimately wants to build the “anti-Robinhood.”

Harsha Mokkarala, founder and CEO of e:cue, joins Terminal Value to discuss why go-to-market analytics is still so fragmented — and how AI data analysts could change the way revenue teams operate.

We cover why marketing, sales, and finance often have different versions of the truth, why dashboards can create more reconciliation than clarity, how e:cue is building Q as a C-suite GTM analyst, and why the future of AI in revenue teams may move from insight to action.

Insurance distribution is one of the last analog corners of software — and AI is moving in fast. In this episode of Terminal Value, Nik Singh sits down with Vlada Lotkina, co-founder and CEO of SuperAgent, to discuss why insurance brokerages have become one of the clearest targets for AI labor, and what it means to put an autonomous sales workforce inside an agency.
Vlada lays out the "perfect storm" reshaping the industry: roughly a quarter of agency staff and owners are set to retire in the next four to five years, new agents take months to ramp, and margins are compressing at the same time. Most insurance AI has gone after the carrier side — underwriting, claims, the back office — but SuperAgent is built for the front end of distribution, where the majority of premium still flows through brokers and their customer relationships. She walks through how the product works as a multi-agent system: real-time coaching and AI role-play to bring every rep to the same bar, plus autonomous outreach that resurfaces the thousands of aged leads and former customers most agencies are already sitting on, opens conversations, and drafts quotes for a human to close.
Nik and Vlada also get into the harder questions — where the human stays in the loop, why SuperAgent is built to grow revenue rather than just cut cost, how AI pricing is shifting from subscriptions and credits toward outcome-based models, how roll-ups and M&A are pushing small agencies to become technology-forward, and why being AI-native beats bolting AI onto legacy systems in a multi-trillion-dollar market.
Guest: Vlada Lotkina, Co-Founder & CEO of SuperAgent