The Twenty Minute VC (20VC) – Ariel Cohen, CEO & Co-founder of Navan (Feb 7, 2026)

Episode Overview

Harry Stebbings sits down with Ariel Cohen, co-founder and CEO of Navan, following Navan's dramatic post-IPO ride—from a $6.2B market cap at IPO to $2.8B in the current market. The discussion unpacks why Navan went public, the reality of IPO mechanics, the scrutiny and morale impact on public company CEOs, and—pivotally—Navan’s bold bets on AI, especially around its in-house customer service agent. Cohen offers candid insights into the pressures of public markets, the competitive landscape, building resilient company culture, and the rapidly evolving world of AI.

Key Discussion Points & Insights

1. The IPO Process: Motives, Mechanics, and Experience

• IPO Motivations (06:21):
  • Multiple factors drove Navan to go public—capital structure post-COVID, advantages for the payments business ("huge advantage to be a public company in the way you raise capital"), and increasing enterprise customer traction demanding public company transparency.
  • Cohen notes timing is unpredictable; once committed, “you are on the road” regardless of market turbulence.
• Experience Sharing the Story (04:50):
  • Enjoyed “summarizing 10 years in the making into 15 slides” for a new, wider audience of public market investors and analysts.
  • Less enjoyable: the added communication burden—“it changes the way you speak and talk with your employees and board” due to regulatory requirements.

2. Competing Public vs. Private—Ramp, Concur, Amex

• Competitive Anxiety (10:30):
  • Cohen asserts culture, not “private market elasticity,” is the key defense; private companies can “spend like crazy,” but “it doesn’t create a good business.”
  • “Our culture is what matters and that’s what will keep us around...” (12:07)
  • The only real competitive fear: “the one that I don’t know about... the Navan of 10-11 years ago, ignorant but really, really good...” (12:24)
• AI Paranoia, Its Genesis (13:30):
  • Cohen recounts a pivotal moment witnessing ChatGPT’s early demo by Sam Altman—“if we will not build our own platform... we are so dead.” (13:54)

3. Wall Street Perception—What Are They Missing?

• Non-Traditional Business Model (14:30):
  • Investors struggle: Navan’s a SaaS-tech business but revenue is “consumption-based”—costs hit up front, returns accrue over years.
  • Churn is ultra-low; “rare that companies are leaving Navan.”
• AI Story Not Priced In (14:30):
  • “100% not,” Cohen says—markets lump all software together, missing vertical AI differentiation.
  • “[We] have our own AI destiny... our own platform that actually understands how to support you—not resetting a password, but how to change a very, very complex trip...” (18:45)

4. Building Vertical AI: Buy vs. Build

• Why Build In-House? (20:45):
  • “There is nothing even remotely close to what is needed when you go to a complex vertical out there... even the APIs [from OpenAI, Anthropic] are not enough.”
  • Zero tolerance for LLM hallucination in travel: “You’ll lose the customer and get a lawsuit.” (20:51)
  • Navan’s platform blends vendor models, open source, and Navan’s own agentic platform for deep, safe integration.

5. Why Most Software Is ‘Dead’ & The Future of AI

• Software’s Future (16:40):
  • Cohen has long called classic, workflow-driven SaaS “dead,” especially with new consumption experiences enabled by AI.
  • “If the user is not happy to use me... you will get disrupted.” (17:10)
• Distribution vs. Delight (17:10):
  • Even distribution moats (e.g., Salesforce) aren’t enough if users loathe the software—Navan's ultimate moat is user/designer love: “If the user loves you... that’s the biggest moat.” (17:13)

6. AI Infrastructure, Open vs. Closed Models, and Future Cycles

• Choice of LLM (25:18):
  • Navan blends “models supervising other models," cherry-picking by task; integration and PI security key concerns for enterprise.
  • “Regulation is big—travel and fintech are licensed globally. We bake all of this in.” (27:01)
• Frontier Model Churn (25:40):
  • Use is “moving much more to Google recently,” but cycles shift; “Anthropic... a massive change... I’m actually re-thinking our engineering.” (25:40)
• The Real AI Revolution (22:23):
  • “People underestimate the size of this change... it’s so much bigger, so much faster... but there’ll be crazy cycles, booms and busts.”
  • “Will our work lives be better? I’m an optimist—yes.”

7. Talent, Culture, and Public Market Pressure

• Morale and Stock Price (40:57):
  • Share price “100%” affects employee morale—even if the CEO doesn’t obsess over it, “a lot of Navan employees are refreshing their app all day long... it’s my role to bring them on the journey and point to what I know about the company.” (40:57)
  • Cohen references the famous “Bezos down-market” letter to reinforce the long-term view.
• Are Any Public Company CEOs Actually Happy? (37:03):
  • “You have a mechanism that makes people obsessed with refreshing their screen... It creates a burden to explain to your employees.”
  • “That doesn't make me excited about that part. Can you find happy CEOs? But I do like the other parts that come with it.” (37:03)

8. Developer Productivity & Org Changes from AI

• Vibe Coding and Product-Market Fit (28:29, 31:04):
  • Navan’s agentic platform enables “vibe coding”—product managers become empowered to prototype themselves.
  • Engineering investment “mainly to AI-related projects... That’s a huge change.” (33:01)
  • “Elon, [cofounder], over a weekend, completely vibe coded our expense product.” (28:29)

9. Personal Principles, Mistakes, and Reflection

• Career Regrets (44:38):
  • Cohen would have “started Navan earlier” had he known, “probably Navan would be significantly bigger...” (44:38)
  • Discussion on parenting: “Invest the time in your kids. Five, six years ago, I didn’t; in the last three years, I have. Nothing is more rewarding.” (48:22)

Notable Quotes & Memorable Moments

• On Going Public:
  • "You're bringing your story and what we've built... summarizing 10 years in the making into, I don't know, 10 to 15 slides plus a document, the S1." – Ariel Cohen [05:00]
• On Competitors:
  • "I never wake up in the morning being worried about a known competitor... The only competitor that I'm worried about, the one that I don't know about." – Ariel Cohen [12:20]
  • "If we will not build our own platform right now, like right now we are so dead." – Ariel Cohen, recounting his panic after Sam Altman’s ChatGPT demo [13:58]
• On Wall Street Missing the AI Story:
  • "100% not. The market... doesn't price in an AI story." – Ariel Cohen [14:30]
• On Building Proprietary AI:
  • "You cannot have any type of hallucination. When I'm changing your flight... you're going to lose the customer but you're also going to get a lawsuit." – Ariel Cohen [20:51]
• On User-First Moats:
  • "If the user loves you, if the employees love you, that's the biggest moat that you can have." – Ariel Cohen [17:15]
• On Public Company Pain:
  • "I don't know one happy public company, CEO. I don't know one. Not one." – Jason Lemkin, quoted by Harry [36:50]
  • "It creates a burden to explain to people, your employees... Everyone is obsessed with their share price." – Ariel Cohen [37:03]
• On AI’s Real Impact:
  • “People are obsessed with LLM infra... it’s a very commoditized kind of thing. If you focus instead on real benefits—AI is already making our customer experience better.” – Ariel Cohen [23:30]
• On Parenting and Priorities:
  • "Nothing is more rewarding than [investing in quality time with your kids]... I regret not doing it earlier. I'm not doing it anymore." – Ariel Cohen [48:22]

Timestamps for Important Segments

| Timestamp | Segment | |---------------|-------------| | 04:45 | IPO process: anticipation vs. reality | | 06:21 | Why Navan chose to go public, timing, and capital structure | | 10:30 | Public vs. private competition, long-term culture vs. private market spending | | 12:20 | The real competitors and the birth of Navan’s AI urgency | | 14:30 | What public markets miss about Navan’s business model and AI story | | 16:40 | Why Cohen believes most SaaS software is “dead” with AI shift | | 17:15 | User delight and retention as ultimate moat | | 20:45 | Build vs. buy for customer service AI and why generic LLMs aren’t enough | | 25:18 | How Navan picks AI models and future AI infrastructure commoditization | | 28:29 | “Vibe coding”, engineering shifts, and product-manager empowerment | | 37:03 | CEO happiness, share price fixation & leadership challenge post-IPO | | 40:57 | Stock price and company morale—Cohen’s emotional management of the team | | 44:38 | Cohen’s career regret: wishing he’d started Navan earlier | | 48:22 | The biggest parenting revelation |

Final Reflections

Big Themes:

• Going public was a strategic necessity, not just a funding event, deeply influencing organizational life and communication.
• Talent, culture, and adaptability (especially paranoia about “invisible” competitors) matter more than private-market spending excess.
• AI is redefining user expectations—winning solutions are deeply verticalized, built in-house due to the complexity and stakes of travel, and no one-size-fits-all platform exists yet.
• Long-term value, resilience, and relentless focus on user satisfaction are Navan’s bet to both outlast downturns and benefit from AI’s next wave.
• Leaders must bear the brunt of external perception (stock price, media narratives) while maintaining internal conviction and employee belief.
• Personal side: Success bought Cohen time for family and self—but he reflects openly on the costs and tradeoffs executives face.

Memorable, Honest, and Full of Pragmatic Insight. An essential listen for founders contemplating IPO, AI transformation, or enduring public market scrutiny.