Due Diligence

topic on 15 shows · 49 statements across 40 episodes

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49 statements about Due Diligence, every show

Indries: Due diligence framework utilizes nearly 170 total questions
“We have a standard of 21 questions, and, you know, we analyze stuff, and wherever we feel that something isn't adding up, we go deeper, and then we go deeper. Just, you know, for the sake of the audience, we have almost a 170 questions total, you know, that we…”
Robert Indries Jun 16, 2026 ▶ 1:23 He Built LLMs in 2016 and Still Trusts Gut Over AI
Schramm: Acquisition due diligence took two months longer than originally expected
“The process of delivering all the due diligence took a little bit longer, and I was hoping to celebrate probably two months earlier than it actually happened”
Anna Schramm May 26, 2026 ▶ 12:32 An Amazon Brand That Became a Business Sale
Minimal Due Diligence Accelerates Small Software Project Acquisitions
“Because I think because they're small projects, there wasn't a huge amount of due diligence, but so it made it really smooth and quick processes in both cases.”
Tom Ulman Oct 14, 2025 ▶ 11:37 From Two Small Projects to Profitable Exits on Acquire.com
Masson: Triangulate contradictory data sources to spot investment risks
“And triangulating these three things together, looking for conflicting contradictory data is often the most interesting to highlight those areas of risk.”
Sid Masson Sep 19, 2025 ▶ 5:19 Transforming Due Diligence with AI: Wokelo’s Automation of Private Market Research and Risk Analysis
Kelly: First-Time Founders Face Audits While Serial Founders Get Conversational Diligence
“If you're an early stage startup and you're a new founder, they're going to spend more time doing due diligence that, and you need to be prepared for that. You know, you're a founder of a startup that's had several successful exits and have had several success…”
Scott Kelly Sep 16, 2025 ▶ 24:24 Start With the End in Mind Before You Take a Single Dollar
Y COMBINATOR Assertion Not checkable as stated
Legora's AI grid reduces legal due diligence from days to minutes
“You realize like, holy shit, this is transformational. It's taking tasks, which used to be, you know, days or hours and it's turning them into minutes.”
Max Junestrand Aug 26, 2025 ▶ 5:58 How This 25-Year-Old Built A $675M Legal AI Startup (With No Legal Experience) · Y Combinator
Legal due diligence commoditized as clients refuse paying for manual review
“And now it's becoming almost a commodity where you're expected to do it, but clients are also not really that excited to pay for Very simple contract review when they know that AI can do, you know, 99% of it.”
Max Junestrand Aug 26, 2025 ▶ 11:24 How This 25-Year-Old Built A $675M Legal AI Startup (With No Legal Experience) · Y Combinator
Junestrand: Undifferentiated work and price pressure force law firms into AI adoption
“A lot of legal work is low differentiation. You know, if you're doing a DD from, you know, law firm X or law firm Y, kind of getting the same deal. And so when you have this perfect Equilibrium of services and somebody disrupts that by taking a new approach. C…”
Max Junestrand Aug 26, 2025 ▶ 12:44 How This 25-Year-Old Built A $675M Legal AI Startup (With No Legal Experience) · Y Combinator
Junestrand: Legal AI will not cause a pricing race to the bottom
“And it, and it's also not a race to the bottom in terms of pricing. Because if you pull down, let's say the cost of a due diligence, you free up more time to spend with a board on advising them on, you know, a really complex merger or a really complex acquisit…”
Max Junestrand Aug 26, 2025 ▶ 14:19 How This 25-Year-Old Built A $675M Legal AI Startup (With No Legal Experience) · Y Combinator
Khan: Founders Must Prepare Technical Asset Transfers Before Due Diligence Starts
“Try to build a product that is very easy to transfer and get ready things done before even the due diligence process started, because you, at the end of the day, you have to transfer the assets, right? So be prepared yourself so that there is very less time be…”
Umar Khan Aug 25, 2025 ▶ 14:33 Simple Steps to Get a Bootstrapped AI Startup Acquired
Gazdecki: Isolate cloud accounts across startups to simplify due diligence
“Having all of your accounts separate, not having like your AWS account mixed with four other different startups or projects just makes everything so much smoother when you get to due diligence and the transfer stage.”
Andrew Gazdecki Aug 25, 2025 ▶ 15:05 Simple Steps to Get a Bootstrapped AI Startup Acquired
BIGDEAL Insight
Sanchez: Only two questions matter in business acquisition due diligence
“The only thing that really matters in due diligence is two things if you're buying a company. Are the numbers real? Because we buy, we don't buy hopes and dreams. We buy realities and cashflow. And two does it seem like the numbers that they gave me will conti…”
Codie Sanchez Aug 18, 2025 ▶ 4:56 Why Playing Small Is Keeping You Broke
Dye: Domain-expert LPs provide crucial due diligence for deal syndication
“Having some folks with some expertise looking at helping us out with diligence and looking over our shoulder on stuff. Not only is it helpful for us as the investment manager, it's also really strong validation for the rest of the LPs to go, oh man, ok, this l…”
AJ Dye Jun 25, 2025 ▶ 12:49 Bridging Investment and Operations: AJ Dye on Scaling Tech with Vertex Innovations and Unifi Ventures
Mehta: I do not spend heavy time on companies post-diligence
“So I'm not really interested in investing a lot of time Except during the beginning stage, which is really the due diligence and making a decision on whether the investment is attractive or not.”
Sahil Mehta Mar 25, 2025 ▶ 3:51 He Took Founders Trekking Before Writing a Single Check
THE PITCH Insight
Chapman: Due diligence cannot predict the post-investment founder relationship
“You never really know exactly what the relationship's gonna be like before you invest, no matter how much diligence you do.”
Jake Chapman Mar 3, 2025 ▶ 31:55 #8 FightCamp (formerly Hykso)
In-person due diligence accelerates M&A timelines and is highly recommended
“So to try to reduce the amount of time for DD, we did a face-to-face, which I'd never done before, but I a hundred percent recommend it.”
Bridget Harris Feb 4, 2025 ▶ 23:51 Capacity Acquires $5m ARR Bootstrapped YouCanBookMe To Build AI Support Mega Platform
Completing due diligence is only half of the M&A acquisition process
“I thought once we're done with due diligence, like, we're done, you know. We just need to sign the contracts and get on with our lives, but Hell no. That was just half of the process.”
Iran Galperin Aug 27, 2024 ▶ 29:08 Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Metelsky: Due Diligence Strips Away Founder Delusion and Exposes Raw Metrics
“During due diligence, you kind of, maybe as a founder, you yourself, you see, You know, business for what it is. Because sometimes as a founder, you know, it's our it's our child, it's our project, and we care about it. So sometimes, you know, we just say, oh,…”
Viktor Metelsky Jul 24, 2024 ▶ 17:30 Startup Acquisitions Stories Podcast With Victor Metelskiy, Founder of Sitekick.ai
Dave Morin asserts that venture investors cannot trust lawyers with diligence
“You can't trust lawyers with diligence.”
Dave Morin Jul 5, 2024 ▶ 25:27 #54: Sun Valley, Tennis and Robots: Summer Adventure Preview · More or Less Podcast
DiGiorgio: Delaying Cross-Border Legal Work Cost Us a Month in M&A
“If I understood it better, I would have started the process as we started due diligence. And not have lost that month in the due diligence to then start the process.”
Bryan DiGiorgio Jun 14, 2024 ▶ 11:29 Startup Acquisition Stories With Bryan Digiorgio, Founder of 1840 & Company
Bureaucratic M&A diligence memos primarily serve to cover corporate liability
“So you see some companies when they're negotiated by a company do this very lengthy and detailed and bureaucratic diligence process and they hire a firm and they write this big huge memo that nobody ever reads and or some wonk reads it but nobody important rea…”
Brad Jacobs Mar 19, 2024 ▶ 1:06:42 Brad Jacobs: How To Build a Billion Dollar Company
20VC Insight
Cassidy: Vendor partner recommendations signal skipped customer due diligence
“Because usually when a partner tells you to pick someone, It means that there's a level of due diligence you didn't really do.”
Brendon Cassidy Mar 8, 2024 ▶ 40:52 Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124 · 20VC with Harry Stebbings
Marshall: LPs can never fully unearth the true motivations of GP firms
“There is so much having worked at three firms that no LP would ever probably unearth, even if they tried. Firms are organic organizations, and no matter how much we think we know, we don't actually know what motivates them.”
Ana Marshall Jan 8, 2024 ▶ 33:30 Ana Marshall – The Climb to Investment Excellence (EP.360)
Gazdecki: A buyer's speed to LOI predicts their pace during due diligence
“The quicker they get to an LOI, or the quicker they get to, you know, responding to questions they ask, or sending you additional questions they may have, that's kind of what Due diligence is going to be like. If it's really slow getting the LOI, if it's reall…”
Andrew Gazdecki Aug 22, 2023 ▶ 21:09 Startup Acquisition Stories with Mark Spera, Co-founder of GrowthBar
Gazdecki: Never stop selling the business after signing an LOI
“When you sign an LOI, don't stop selling. Do not stop selling the business. Like you're going to have all this stuff that the buyer wants. Right. What you should also always do is record like a loom on how marketing works, how sales works, how showcase me, you…”
Andrew Gazdecki Aug 15, 2023 ▶ 41:22 Startup Acquisition Stories with Josh Kim, Founder of The Cubby
20VC Insight
Lemkin: VC due diligence is purely confirmatory after deal decisions are made
“And why it's because the diligence is always confirmatory. VCs decide they want to do the deal and they don't want to hear reasons to not do it.”
Jason Lemkin Aug 9, 2023 ▶ 51:39 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Gazdecki: Pitching growth opportunities in diligence prevents deals from falling apart
“When you share that with the buyer doing during due diligence that can exponentially increase the chances of close case, something pops up.”
Andrew Gazdecki Jul 25, 2023 ▶ 16:32 Startup Acquisition Stories with Jeff Richards, Founder of Rayneta
SAASTR Assertion Not checkable as stated
Lemkin: VCs Intentionally Skipped Diligence During 2021 Peak
“The pace of investing was fast, so fast and furious that people intentionally did not do the diligence, ok? It was an intentional choice”
Jason Lemkin May 18, 2023 ▶ 38:24 VC AMA with SaaStr CEO Jason Lemkin and Black Mangroves MD Arnaud Bonzom at SaaStr APAC 2023
Stefurak provides proof of earnings and extra context before buyers ask
“I show proof of earnings and ask for the set of questions, and I'm always proactive at any stage, and I tend to demonstrate and explain more than they ask for.”
Igor Stafurak May 16, 2023 ▶ 12:13 Startup Acquisition Stories with Ihor Stefurak, Co-founder of Mentalwalk
Stefurak: Recorded walkthrough calls are the most effective due diligence method
“And I think that the most effective way to investigate because buyers can record the section, the session and watched later.”
Igor Stafurak May 16, 2023 ▶ 12:37 Startup Acquisition Stories with Ihor Stefurak, Co-founder of Mentalwalk
FOUNDER'S JOURNAL 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 How Founders Should Be Integrating AI To Their Business
Gazdecki: Asset transfer can be harder than due diligence in acquisitions
“Transferring assets can sometimes be harder than due diligence, just because, like, I've heard stories of people having, you know, some really good products or businesses inside of a single AWS account, they got to pull it out Or a Stripe account with multiple…”
Andrew Gazdecki Mar 28, 2023 ▶ 14:50 Startup Acquisition Stories with Lotanna Ezeike, Founder of Creator Check
Clueless Buyers in Due Diligence Lack Post-Acquisition Plans
“I think if somebody in due diligence is really clueless what to do, what to ask for, it also kind of shows they don't have any plan on what to do with the business after that”
Tim Schmidbauer Jun 6, 2022 ▶ 13:49 Startup Acquisition Stories with Tim Schmidbauer - Co-Founder of Inlytics
Bhaskaran: Acquirers should lock in price before doing due diligence
“The only, my, only thing that really matters is like, dude, how much are you going to pay? That's it, right? So get that conversation, at least that's what I do, get that conversation out of the way first. And then start worrying about the diligence and everyt…”
Vivek Bhaskaran May 3, 2022 ▶ 20:20 He Acquired Companies through Whatsapp. Bootstrapped with $30m in revenue today.
Dowling: Allocators should conduct virtual due diligence individually to read dynamics
“Do calls individually. It's really difficult to do a group Zoom or Teams call in terms of due diligence because you might have people talking over each other. You can't pick up on individual Brady Bunch boxes that when the senior PM talks, the number two rolls…”
Greg Dowling May 2, 2022 ▶ 30:14 Greg Dowling – Mid-Market Institutional Consulting at FEG (Capital Allocators, EP.248)
CAPITAL ALLOCATORS Prediction Not checkable as stated
Dowling: Allocator due diligence will permanently shift to hybrid virtual-in-person models
“You ask, where is it going? I think it's going to be a little bit of both. I think our meetings will be more meaningful, and that instead of doing a marathon all day meeting on site where we're exhausted and they're exhausted, or flying to Hong Kong and our ey…”
Greg Dowling May 2, 2022 ▶ 31:20 Greg Dowling – Mid-Market Institutional Consulting at FEG (Capital Allocators, EP.248)
Casel: Preparing due diligence materials pre-listing drastically reduces in-deal workload
“A lot of the due diligence work, like getting my books in order, getting, you know, just getting the things that I know that they're probably going to ask for doing a lot of that prep work even before I listed helped, helped a lot so that by the time it got in…”
Brian Casel Mar 28, 2022 ▶ 18:02 Startup Acquisition Stories with Brian Casel - Founder of ZipMessage
NEON SHOW Insight
Baid: Prudent investors must review ten years of annual reports and filings
“A prudent investor never purchases ownership in a business without conducting the necessary due diligence. You should study about the company and its competitors, both listed and unlisted from company website, company filings, information on the internet, and …”
Gautam Baid Feb 7, 2022 ▶ 31:49 The Joys of COMPOUNDING with Gautam Baid!
Reed: Due diligence depth is constrained by acquisition deal size
“I think that there is a limited amount of due diligence that you can do depending on the deal size, and so I think I probably over complicated that part of the process when I first got started.”
Tara Reed Nov 15, 2021 ▶ 4:24 Startup Acquisition Stories with Tara Reed CEO at Apps Without Code
Reed: Formal technical due diligence is unhelpful for micro-SaaS acquisitions
“I actually worked with a due diligence company, actually, who, like, went to the code base and did all of that work, and I felt like they It just wasn't all that helpful at the deal sites that I was doing to get that level of, like, there were things that were…”
Tara Reed Nov 15, 2021 ▶ 19:22 Startup Acquisition Stories with Tara Reed CEO at Apps Without Code
WE LIVE TO BUILD Assertion Supported
Rusk: Spending Over 20 Hours on Due Diligence Yields Higher Investment Success
“If you spend, you know, more than 20 hours doing due diligence, the success of the investment is going to be higher. I don't remember how much it is, but it's like a double digit percentage higher.”
Misty Rusk Jun 8, 2021 ▶ 17:51 The 'Culture of Yes' Secret Behind a $300K Angel Fund
Walling: Acquirers and investors require IP agreements from every code contributor
“If you ever want to sell your company, if you ever want to raise investment, when they get into due diligence, they're going to ask you and they're going to make you sign something that says every person who has touched this code or every person who has contri…”
Rob Walling Sep 22, 2020 ▶ 5:46 Episode 515 | Finding a Co-Founder, Getting Better at Sales, and More Listener Questions
NEON SHOW Disclosure
Shivani: YourNest takes at least 12 weeks from initial outreach to fund disbursement
“From the day you write to us to a term sheet is anywhere between six to eight weeks, if not more. And from a term sheet to a dispersal is another 10 to 12 weeks, depending on what is your readiness on the, you know, from our due diligence perspective. So it's,…”
Girish Shivani Aug 15, 2019 ▶ 23:23 100xEntrepreneur | Episode 6 | Girish Shivani, Co-founder and Partner at Yournest Venture Fund
Moodgal: Allocator Due Diligence Expanded From Six Weeks to 18 Months
“If you put it in a time spectrum, I would say what used to take six weeks now takes 18 months.”
Rahul Moodgal Feb 18, 2019 ▶ 34:41 Rahul Moodgal - Master Fund Raiser (Capital Allocators, EP.87)
Moodgal: Investors Who Take Longer to Diligence Stay Invested Longer
“The longer that someone takes, the longer they're going to be with you.”
Rahul Moodgal Feb 18, 2019 ▶ 35:14 Rahul Moodgal - Master Fund Raiser (Capital Allocators, EP.87)
20VC Insight
Hyper-fast crypto fundraising rounds force VCs to skip technical due diligence
“Yeah, I think what it does is it forces venture capitalists to make decisions that aren't entirely informed. So if you actually read a white paper it's basically 30 pages of really technical information that requires diligence, which you couldn't possibly do i…”
Jeff Morris Jr. Nov 19, 2018 ▶ 20:44 20VC: Investing Lessons From Observing Doug Leone and Bill Gurley, Why It Is Easier To Be Contrarian As A VC Than As An Angel & What It Takes To Run Tinder's Product and Revenue Alongside A Seed Fund with Jeff Morris Jr, Founder @ Chapter One
Scheer: Checklist-free, bespoke due diligence outperforms rigid box-checking
“I think it's valuable to Make it up as you go along because it allows you flexibility to adapt to changing market environment, to identify the key issue or issues at each individual firm, and every one of these is different, and also enables you to learn each …”
Karl Scheer Oct 29, 2018 ▶ 38:03 Karl Scheer – Competing Sensibly as CIO of the University of Cincinnati (EP.74)
Nathan Latka: Due Diligence Is the Graveyard Where Deals Fall Apart
“Between the LOI signing and the actual money being exchanged when the deal potentially closes, there's this big period of due diligence, and guys, this is like the graveyard. This is where deals fall apart.”
Nathan Latka Mar 4, 2016 ▶ 2:18 My Company Was Just Acquired, Here's Whats Next with Nathan Latka
Nathan Latka: Founders Must Maintain Alternative LOI Leverage During Due Diligence
“Due diligence is a pain in the butt, but look, you have to keep leverage when you're doing these deals, and I had a hundred percent confidence that if it fell through, we could very easily go back to one of the other companies who made an offer in one of their…”
Nathan Latka Mar 4, 2016 ▶ 3:24 My Company Was Just Acquired, Here's Whats Next with Nathan Latka

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