About AI to Go Podcast I Real Talk on Enterprise AI
Let's be honest: Enterprise AI has a trust problem. Vendors overpromise. Buyers overthink. Pilots die in silence. And everyone's too polite - or too scared - to say what actually went wrong.
AI to Go is the Enterprise AI podcast that breaks the silence. Every episode is an honest, no-BS conversation between the people building AI and the people buying it inside large organizations - about what actually works, what quietly fails, and why most AI pilots never make it to production.
I'm Johannes Deubener, an AI Implementation Lead at Deutsche Telekom based out of San Francisco. As a former marketplace founder who spent years helping sellers find buyers, I've been on both sides of the table. Now I'm the person inside the enterprise evaluating which AI vendors to pilot and put into production.
That dual perspective shapes every conversation on this show.
Each week, I sit down with AI startup founders, enterprise leaders, investors, and AI ecosystem experts for real talk about:
→ Why most enterprise AI pilots fail - and the few things that make the difference between production and purgatory
→ How enterprise buying decisions actually get made (spoiler: it's not how vendors think)
→ How to navigate complex stakeholder setups across the enterprise
→ The fears and frustrations that both sides need to say out loud
→ How AI vendors can design pitches, demos, and pilots that actually survive contact with a real enterprise
AI founders and enterprise leaders are both short on time and drowning in hype. AI to Go exists because your scarcest resources - time, attention, and focus - deserve better than the FOMO-fueled AI podcasts telling you the sky is falling or rising every week.
The mission is simple: create mutual understanding between enterprise AI buyers and sellers so we can stop wasting each other's time and start building AI deployments that actually work for both sides.
New episodes every Tuesday. Subscribe so you don't miss one.
🔗 LinkedIn: https://www.linkedin.com/company/ai-to-go-podcast/
This Founder Said No to 90% of the Market - and Won. How to Build Your Enterprise Niche
Most AI founders try to sell to everyone. Chris Carter said no to more than 90% of the software enterprise market - and built two successful enterprise companies from that single decision.
Chris Carter (Chairman & CEO of Approyo, Founder of Mugatu AI) has started 11 companies, sold several, and managed a bankruptcy. In this episode, he breaks down how AI founders should pick their enterprise niche and ecosystem, how to be successful in Enterprise, and which Scotch to pick for your first closed Enterprise AI deal.
Timestamps
01:02 What Chris saw in SAP HANA in 2013 that everyone else missed
02:58 Why he said no to 90% of the market
04:59 Which platforms should you embed into before it's obvious?
05:34 Mugatu AI: Why he's building an AI security layer for enterprises
11:56 How to validate startup ideas using AI (Gemini as your thought partner)
15:23 Several exits, one bankruptcy: The failure that shaped everything
18:26 His 20% Rule: Never let one client exceed 20% of your revenue
20:10 Train first, find the champion, sell top-down: The enterprise implementation framework
22:25 How to find and cultivate an internal champion before your pilot starts
23:43 The biggest gap AI founders have when building for enterprise
25:42 How to instantly build credibility in an enterprise room (Chris's top 4 list)
29:19 Behind closed doors: The most broken SAP implementation Chris ever inherited
33:25 Why AI pilots die in procurement
36:10 Managing the tension between your internal champion and the C-suite
36:56 The middle management trap
44:07 SAP in 5 years
45:48 Scotch pick for your first enterprise deal closed
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Connect with Johannes: https://www.linkedin.com/in/johannesdeubener/ (https://www.linkedin.com/in/johannesdeubener/)
Read Johannes' Newsletter "Inside Enterprise AI": https://johannesdeubener.substack.com/ (https://johannesdeubener.substack.com/)
Follow Chris on LinkedIn: https://www.linkedin.com/in/christopher-carter-885159/ (https://www.linkedin.com/in/christopher-carter-885159/)
Check out Approyo: https://approyo.com/ (https://approyo.com/)
Check Out Mugatu AI: https://mugatuai.com/ (https://mugatuai.com/)
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More about AI To Go: I Real Talk on Enterprise AI
✨ Watch more Episodes on YouTube: https://www.youtube.com/channel/UCiL3_cC9nmXALQiaqlYs2Kw (https://www.youtube.com/channel/UCiL3_cC9nmXALQiaqlYs2Kw)
✨ Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/ai-to-go-podcast/id1866997458 (https://podcasts.apple.com/us/podcast/ai-to-go-podcast/id1866997458)
✨ Listen on Spotify: https://open.spotify.com/episode/5X9XgIv1qtCYtExziNMyXK (https://open.spotify.com/episode/5X9XgIv1qtCYtExziNMyXK)
✨ Receive all Podcast Updates on LinkedIn: https://www.linkedin.com/company/ai-to-go-podcast/ (https://www.linkedin.com/company/ai-to-go-podcast/)
7 Apr 2026
AI Demo Trap: Client Loved It, Then Ghosted - Why This Keeps Happening
Most AI demos never reach production. Here's why - and what to do differently.
Tim Daines, Dubai-based founder of Synaptix Solutions and a 22-year expert of AI, data, and enterprise transformation, breaks down the hard truths founders and enterprise leaders refuse to hear: the real reason AI ROI keeps vanishing, why your data strategy is the actual bottleneck, and shares the strategic lessons that only come from being inside the room when enterprise AI succeeds and when it spectacularly fails.
Whether you're an AI founder trying to crack enterprise sales, an executive navigating AI transformation, or a VC watching portfolio companies struggle to demonstrate ROI - this episode will fundamentally change how you think about AI in production.
⏱️ Timestamps
0:00 Intro
1:15 The Sacrifice Behind Building a Business in Dubai
3:08 Enterprise Maturity in the Gulf
5:30 Dubai as an AI Hub
7:57 Why Relationships Beat a Killer Deck in Dubai
8:55 Why VC AI Portfolio Companies Are Struggling to Demonstrate ROI
9:08 The "Peloton Problem": Why AI Demos Don't Survive Contact With Reality
12:15 What Winning Founders Do Differently
17:42 Minimum Viable Data - The Non-Negotiable Before Any AI Build
19:57 Stop Conflating POC, Pilot & MVP
22:36 The Institutional Knowledge Crisis
26:23 Fast Strategy - Why Traditional Strategy Cycles Are Dangerous in an AI World
32:16 The CFO as the "Adult" in the Room
37:54 Security, Sovereignty & Why IT Must Be in Every AI Room
38:16 Why The Intelligence Integration Layer Is Next
41:22 Where to Find Tim
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Connect with Johannes: https://www.linkedin.com/in/johannesdeubener/ (https://www.linkedin.com/in/johannesdeubener/)
Read Johannes' Newsletter "Inside Enterprise AI": https://johannesdeubener.substack.com/ (https://johannesdeubener.substack.com/)
Follow Tim on LinkedIn: https://www.linkedin.com/in/tim-daines/ (https://www.linkedin.com/in/tim-daines/)
Read Tim's Substack: https://productagent.substack.com/ (https://productagent.substack.com/)
"Fast Strategy" Book: https://www.abebooks.com/9780273712442/Fast-Strategy-Strategic-Agility-Will-0273712446/plp (https://www.abebooks.com/9780273712442/Fast-Strategy-Strategic-Agility-Will-0273712446/plp)
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More about AI To Go: I Real Talk on Enterprise AI
✨ Watch more Episodes on YouTube: https://www.youtube.com/channel/UCiL3_cC9nmXALQiaqlYs2Kw (https://www.youtube.com/channel/UCiL3_cC9nmXALQiaqlYs2Kw)
✨ Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/ai-to-go-podcast/id1866997458 (https://podcasts.apple.com/us/podcast/ai-to-go-podcast/id1866997458)
✨ Listen on Spotify: https://open.spotify.com/episode/5X9XgIv1qtCYtExziNMyXK (https://open.spotify.com/episode/5X9XgIv1qtCYtExziNMyXK)
✨ Receive all Podcast Updates on LinkedIn: https://www.linkedin.com/company/ai-to-go-podcast/ (https://www.linkedin.com/company/ai-to-go-podcast/)
24 Mar 2026
The AI Vendor Culling Is Coming - Here's How You Survive It | Russ Fradin, Larridin
In this conversation, host Johannes Deubener sits down with serial founder Russ Fradin, CEO of Larridin (backed by Andreessen Horowitz). He shares what 30 years of building enterprise companies teaches you about AI adoption, vendor survival, and long-term customer relationships.
We cover the real #1 driver of enterprise churn, why 85% of leaders fear falling behind in the next 18 months, what shadow AI really signals about enterprise adoption, and why teams that build with AI dramatically outperform teams that only summarize.
We go deep on what it actually takes to win in the enterprise - not just to get in the door, but to be one of the AI vendors still standing when the inevitable AI vendor consolidation hits.
Chapters
00:41 - Russ Fradin intro
02:28 - The repeat founder trap
06:01 - The $5M ARR pivot
09:25 - 30 years of enterprise lessons: what AI founders need to know right now
09:30 - The #1 driver of enterprise churn
13:07 - Radical honesty as your competitive moat
15:45 - First-time founder playbook
16:02 - Why free pilots fail - and how to create the right friction from day one
19:09 - How to close the gap from pilot to production
22:53 - The 2026 Enterprise AI Report
26:28 - The coming AI vendor culling
29:30 - What the AI leaders do differently
31:54 - Why IT teams get 10x more from AI
32:11 - The global knowledge workforce retraining experiment
35:27 - Shadow AI: 45% of AI adoption happens outside procurement
38:54 - When tool sprawl becomes organizational waste
41:05 - The power user gap
44:03 - Why HR needs to own AI enablement - not just IT
48:10 - What Larridin actually does: measuring AI productivity across the enterprise
54:27 - "Software eating labor": is AI substituting or augmenting work?
54:42 - Why AI will create more jobs
59:06 - Where to find Russ
59:29 - Outro
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Connect with Johannes: https://www.linkedin.com/in/johannesdeubener/ (https://www.linkedin.com/in/johannesdeubener/)
Follow Russ: https://www.linkedin.com/in/rfradin/ (https://www.linkedin.com/in/rfradin/)
Check out Larridin: https://larridin.com/ (https://larridin.com/)
Read the 2026 Enterprise AI Report: https://larridin.com/state-of-enterprise-ai (https://larridin.com/state-of-enterprise-ai)
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More about AI To Go: I Real Talk on Enterprise AI
✨ Watch more Episodes on YouTube: https://www.youtube.com/channel/UCiL3_cC9nmXALQiaqlYs2Kw (https://www.youtube.com/channel/UCiL3_cC9nmXALQiaqlYs2Kw)
✨ Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/ai-to-go-podcast/id1866997458 (https://podcasts.apple.com/us/podcast/ai-to-go-podcast/id1866997458)
✨ Listen on Spotify: https://open.spotify.com/episode/5X9XgIv1qtCYtExziNMyXK (https://open.spotify.com/episode/5X9XgIv1qtCYtExziNMyXK)
✨ Receive all Updates on LinkedIn: https://www.linkedin.com/company/ai-to-go-podcast/ (https://www.linkedin.com/company/ai-to-go-podcast/)
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