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May 16, 2023 · 51m · founders-journal

How Founders Should Be Integrating AI To Their Business

Jesse Pujji · 26m spoken Alex Lieberman · 19m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this in-person episode of The Crazy Ones, co-hosts Alex Lieberman and Jesse Pujji evaluate actionable business opportunities in artificial intelligence and analyze strategies for scaling specialized startup ventures like executive ghostwriting and private equity due diligence. They also share hard-won operational advice on founder productivity, AI tool integration, and managing startup advisory boards.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 41.9% of the talking time here. How this is scored →

Alex as informed peer 5.2 Guest teaching 2.8 Guest disagreement 1.8 Alex pushing back 1.8
05100:0015:0030:0045:000:03–3:47 · Alex as informed peer 2/10 In-Person Reunion and Morning Brew Studio Tour Alex and Jesse catch up warmly in person at Morning Brew's studio. The conversation is entirely lighthearted banter and mutual appreciation of their physical office spaces.3:47–15:16 · Alex as informed peer 6/10 Evaluating the AI Boom and Opportunity Frameworks Alex and Jesse evaluate the AI wave, with Alex drawing analogies to electricity and Shopify app ecosystem rollups. Jesse outlines a vertical versus horizontal opportunity matrix while Alex presses on the defensibility of wrapper tools like Jasper.15:16–24:24 · Alex as informed peer 6/10 Brainstorming AI Applications in Travel and Fashion Alex immediately questions why Jesse's travel assistant concept requires AI rather than traditional search before both brainstorm monetization via hotel commissions. Alex then pitches his own idea for an AI computer-vision wardrobe stylist.24:24–31:14 · Alex as informed peer 7/10 Implementing AI to Scale Operations and Content Creation Alex shares the operational mechanics of his ghostwriting agency and details an automated workflow using voice memos and transcripts to scale ghostwriter capacity. Jesse validates the concept through his own portfolio workflows.31:14–43:21 · Alex as informed peer 5/10 Launching Aux Insights and Due Diligence Strategy Jesse forcefully dismisses the corporate label 'operator' before detailing his new PE due diligence venture Aux Insights. Alex synthesizes how the venture can serve as a wedge into broader consulting and training offerings.0:03–3:47 · Guest teaching 0/10 In-Person Reunion and Morning Brew Studio Tour Alex and Jesse catch up warmly in person at Morning Brew's studio. The conversation is entirely lighthearted banter and mutual appreciation of their physical office spaces.3:47–15:16 · Guest teaching 4/10 Evaluating the AI Boom and Opportunity Frameworks Alex and Jesse evaluate the AI wave, with Alex drawing analogies to electricity and Shopify app ecosystem rollups. Jesse outlines a vertical versus horizontal opportunity matrix while Alex presses on the defensibility of wrapper tools like Jasper.15:16–24:24 · Guest teaching 3/10 Brainstorming AI Applications in Travel and Fashion Alex immediately questions why Jesse's travel assistant concept requires AI rather than traditional search before both brainstorm monetization via hotel commissions. Alex then pitches his own idea for an AI computer-vision wardrobe stylist.24:24–31:14 · Guest teaching 2/10 Implementing AI to Scale Operations and Content Creation Alex shares the operational mechanics of his ghostwriting agency and details an automated workflow using voice memos and transcripts to scale ghostwriter capacity. Jesse validates the concept through his own portfolio workflows.31:14–43:21 · Guest teaching 5/10 Launching Aux Insights and Due Diligence Strategy Jesse forcefully dismisses the corporate label 'operator' before detailing his new PE due diligence venture Aux Insights. Alex synthesizes how the venture can serve as a wedge into broader consulting and training offerings.0:03–3:47 · Guest disagreement 1/10 In-Person Reunion and Morning Brew Studio Tour Alex and Jesse catch up warmly in person at Morning Brew's studio. The conversation is entirely lighthearted banter and mutual appreciation of their physical office spaces.3:47–15:16 · Guest disagreement 2/10 Evaluating the AI Boom and Opportunity Frameworks Alex and Jesse evaluate the AI wave, with Alex drawing analogies to electricity and Shopify app ecosystem rollups. Jesse outlines a vertical versus horizontal opportunity matrix while Alex presses on the defensibility of wrapper tools like Jasper.15:16–24:24 · Guest disagreement 1/10 Brainstorming AI Applications in Travel and Fashion Alex immediately questions why Jesse's travel assistant concept requires AI rather than traditional search before both brainstorm monetization via hotel commissions. Alex then pitches his own idea for an AI computer-vision wardrobe stylist.24:24–31:14 · Guest disagreement 1/10 Implementing AI to Scale Operations and Content Creation Alex shares the operational mechanics of his ghostwriting agency and details an automated workflow using voice memos and transcripts to scale ghostwriter capacity. Jesse validates the concept through his own portfolio workflows.31:14–43:21 · Guest disagreement 4/10 Launching Aux Insights and Due Diligence Strategy Jesse forcefully dismisses the corporate label 'operator' before detailing his new PE due diligence venture Aux Insights. Alex synthesizes how the venture can serve as a wedge into broader consulting and training offerings.0:03–3:47 · Alex pushing back 0/10 In-Person Reunion and Morning Brew Studio Tour Alex and Jesse catch up warmly in person at Morning Brew's studio. The conversation is entirely lighthearted banter and mutual appreciation of their physical office spaces.3:47–15:16 · Alex pushing back 3/10 Evaluating the AI Boom and Opportunity Frameworks Alex and Jesse evaluate the AI wave, with Alex drawing analogies to electricity and Shopify app ecosystem rollups. Jesse outlines a vertical versus horizontal opportunity matrix while Alex presses on the defensibility of wrapper tools like Jasper.15:16–24:24 · Alex pushing back 3/10 Brainstorming AI Applications in Travel and Fashion Alex immediately questions why Jesse's travel assistant concept requires AI rather than traditional search before both brainstorm monetization via hotel commissions. Alex then pitches his own idea for an AI computer-vision wardrobe stylist.24:24–31:14 · Alex pushing back 1/10 Implementing AI to Scale Operations and Content Creation Alex shares the operational mechanics of his ghostwriting agency and details an automated workflow using voice memos and transcripts to scale ghostwriter capacity. Jesse validates the concept through his own portfolio workflows.31:14–43:21 · Alex pushing back 2/10 Launching Aux Insights and Due Diligence Strategy Jesse forcefully dismisses the corporate label 'operator' before detailing his new PE due diligence venture Aux Insights. Alex synthesizes how the venture can serve as a wedge into broader consulting and training offerings.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 57.5% · guest 42.5%0:00 · Alex 57.5% · guest 42.5%3:00 · Alex 62.8% · guest 37.2%3:00 · Alex 62.8% · guest 37.2%6:00 · Alex 47.9% · guest 52.1%6:00 · Alex 47.9% · guest 52.1%9:00 · Alex 42.5% · guest 57.5%9:00 · Alex 42.5% · guest 57.5%12:00 · Alex 28.7% · guest 71.3%12:00 · Alex 28.7% · guest 71.3%15:00 · Alex 27.9% · guest 72.1%15:00 · Alex 27.9% · guest 72.1%18:00 · Alex 22.1% · guest 77.9%18:00 · Alex 22.1% · guest 77.9%21:00 · Alex 63% · guest 37%21:00 · Alex 63% · guest 37%24:00 · Alex 61.9% · guest 38.1%24:00 · Alex 61.9% · guest 38.1%27:00 · Alex 57.9% · guest 42.1%27:00 · Alex 57.9% · guest 42.1%30:00 · Alex 47% · guest 53%30:00 · Alex 47% · guest 53%33:00 · Alex 7.1% · guest 92.9%33:00 · Alex 7.1% · guest 92.9%36:00 · Alex 9.6% · guest 90.4%36:00 · Alex 9.6% · guest 90.4%39:00 · Alex 22.4% · guest 77.6%39:00 · Alex 22.4% · guest 77.6%42:00 · Alex 42.6% · guest 57.4%42:00 · Alex 42.6% · guest 57.4%45:00 · Alex 33.3% · guest 66.7%45:00 · Alex 33.3% · guest 66.7%48:00 · Alex 77.6% · guest 22.4%48:00 · Alex 77.6% · guest 22.4%51:00 · Alex 100% · guest 0%51:00 · Alex 100% · guest 0%
Sharpest disagreement ▶ 31:12 Jesse rejects the term 'operator'

Jesse passionately pushes back against Alex's hiring priorities, attacking 'operator' as a pretentious, condescending label invented by investors.

 Hardest push from Alex ▶ 15:50 Alex challenges the necessity of AI in travel

Alex immediately challenges Jesse's travel planner pitch by demanding to know why the concept genuinely needs AI rather than existing aggregation tools.

 Biggest teaching moment ▶ 38:09 Jesse explains PE due diligence market dynamics

Jesse explains how major firms pay McKinsey $600k-$1M for hand-wavy marketing diligence, revealing the specific market gap Aux Insights targets.

 Alex holds their own ▶ 6:46 Alex compares AI platform dynamics to Shopify rollups

Alex demonstrates strategic business acumen by framing AI LLMs like OpenAI as foundational infrastructure akin to Shopify, predicting plugin rollup ecosystems.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
In-Person Reunion and Morning Brew Studio Tour 2010 Alex and Jesse catch up warmly in person at Morning Brew's studio. The conversation is entirely lighthearted banter and mutual appreciation of their physical office spaces.
Evaluating the AI Boom and Opportunity Frameworks 6423 Alex and Jesse evaluate the AI wave, with Alex drawing analogies to electricity and Shopify app ecosystem rollups. Jesse outlines a vertical versus horizontal opportunity matrix while Alex presses on the defensibility of wrapper tools like Jasper.
Brainstorming AI Applications in Travel and Fashion 6313 Alex immediately questions why Jesse's travel assistant concept requires AI rather than traditional search before both brainstorm monetization via hotel commissions. Alex then pitches his own idea for an AI computer-vision wardrobe stylist.
Implementing AI to Scale Operations and Content Creation 7211 Alex shares the operational mechanics of his ghostwriting agency and details an automated workflow using voice memos and transcripts to scale ghostwriter capacity. Jesse validates the concept through his own portfolio workflows.
Launching Aux Insights and Due Diligence Strategy 5542 Jesse forcefully dismisses the corporate label 'operator' before detailing his new PE due diligence venture Aux Insights. Alex synthesizes how the venture can serve as a wedge into broader consulting and training offerings.

Statements from this episode (13)

Prediction Not checkable as stated
Lieberman: In 20 years, 'AI' will not be a distinct term
“This feels like when we're talking about AI, we're talking about the internet. We're not going to talk, we'll use the words AI, like, 20 years from now, because it will just be how everything operates.”
Alex Lieberman May 16, 2023 ▶ 6:47
Prediction Not checkable as stated
Lieberman: ChatGPT plugins will be worth multiples of Shopify
“Shopify is a sixty billion dollar company right now. I think OpenAI is thirty billion. You would have to think that the plugins to ChatGPT, which are gaining some popularity now as they're opening it up, is going to be multiples of that.”
Alex Lieberman May 16, 2023 ▶ 7:11
Assertion Supported
Pujji: Microsoft Teams is roughly five times the size of Slack
“Apparently Teams is like five times the size of Slack now. Because Microsoft owns the enterprise”
Jesse Pujji May 16, 2023 ▶ 8:06
Prediction Not checkable as stated
Pujji: OpenAI will crush thin horizontal wrapper startups
“I think one of the challenges people to be careful of when building on top of open AI is like, if your solution is too horizontal, they're eventually going to eat your lunch.”
Jesse Pujji May 16, 2023 ▶ 11:56
Insight
Pujji: The biggest AI winners will dominate narrow vertical matrices
“I think the most successful companies is somewhat obvious or not obviously, but it will take one square of that matrix. Like I said, customer service for banking and go, that is a very specific solution. I'm going to have the best models. I'm going to teach, I…”
Jesse Pujji May 16, 2023 ▶ 12:21
Assertion Partly supported
Pujji: Hotels pay travel agents a 25% booking commission
“Hotels. Pay 25%. To this day. So if you get a hotel a booking, you as a travel agent, whether you're online, whether you're a physical person, get 25% of the booking”
Jesse Pujji May 16, 2023 ▶ 20:12
Assertion Not checkable as stated
Pujji: All Kahani code is written with GitHub Copilot
“So we, I mean, all the code for Kahani is written with Copilot. And that's gone on for quite a while.”
Jesse Pujji May 16, 2023 ▶ 24:46
Assertion Not checkable as stated
Lieberman: Ghostwriting agency hit $26K MRR after four weeks
“Now the business today is at 26 K MRR after four weeks. And it's literally just from people in the DMS and me pairing them with ghostwriters.”
Alex Lieberman May 16, 2023 ▶ 26:16
Assertion Not checkable as stated
Pujji: McKinsey and Bain have nine-figure due diligence businesses
“And then, you know, Bain and McKinsey both have nine figure plus businesses in a slightly different form of due diligence.”
Jesse Pujji May 16, 2023 ▶ 36:17
Assertion Not checkable as stated
Pujji: McKinsey charges $600K to $1M per due diligence project
“The McKinsey, just to give you a sense for pricing charges, 600,000 to a million dollars per project. For like four people for a month.”
Jesse Pujji May 16, 2023 ▶ 38:09
Disclosure
Pujji refuses to advise startups without investing his own money
“And so I outright, I am not an advisor to anything that I don't have money into.”
Jesse Pujji May 16, 2023 ▶ 44:40
Insight
Pujji: Advisory boards distract founders from selling to customers
“Building an advisory board is one of the, I'd put it as one of the many distractions that entrepreneurs create to think that they're going to build a better business instead of just selling stuff to customers.”
Jesse Pujji May 16, 2023 ▶ 46:16
Insight
Worthwhile startup advisors should personally invest $25,000 to $50,000
“Anyone who's worth being an advisor probably should have 25 to 50,000 dollars to put into your company.”
Jesse Pujji May 16, 2023 ▶ 49:33
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