How to turn everyday frustrations into AI wins

Your next big AI win may come from someone your leadership team would never think to pick.

In this episode of The Deep View Conversations, we sit down with Todd Earwood, CEO of Betra Works and an AI investor at HalfCourt Ventures, to explore what it takes to deploy AI for useful work inside organizations.
 
Drawing on his work with 1,200 leaders and executives, Todd explains why the people closest to the work often see AI opportunities that executives miss. He shares how a university athletics sales rep used AI to uncover new ticket buyers, how a warehouse employee helped a manufacturer rethink a 22-year-old spreadsheet, and why a skeptical, experienced employee became an unexpected AI champion.

We also discuss Todd's book, Adapt & Adopt, and his approach to teaching people how to identify useful AI tasks, evaluate opportunities, and build momentum from individual wins to broader adoption.

Other topics covered:

• Three paths to putting AI to work in a business
• Why employee frustrations can reveal valuable AI opportunities
• The gap between personal AI use and workplace adoption
• What Todd learned from investing in more than 100 AI companies
• Building a tech career outside San Francisco and New York
• Why meeting recorders and voice dictation can make an immediate difference
• Using Claude to protect your calendar and priorities

If you're leading a team, trying to make AI useful in your own job, or deciding where to start, this conversation offers practical ways to connect AI's capabilities with the work people do every day.

Subscribe to Deep View Conversations for interviews with the leaders shaping the future of AI, business, and technology: https://tdv.transistor.fm/ 

And don't forget to sign up for The Deep View daily newsletter. We don’t just cover AI, we decode it. In a world flooded with hype, we deliver sharp, no-nonsense insights to keep you ahead of the curve and help you put AI to work every day: subscribe.thedeepview.com

TIMELINE
0:00 Introduction
2:27 From AI investing to real-world adoption
7:19 Three paths to making AI useful
10:16 Adapt & Adopt: learning how to think
16:34 Unexpected AI wins in sales and manufacturing
21:14 Finding AI opportunities in the work you hate
23:45 Why your AI champions may surprise you
27:02 Investing in AI before the boom
33:49 Building a tech career beyond the coastal hubs
40:44 Meeting recorders, Wispr Flow and everyday AI
45:24 Using AI to protect your time
48:58 Closing advice: slow down when life gets hard

Creators and Guests

Host

Jason Hiner

Editor-in-Chief of The Deep View

What is The Deep View: Conversations?

From frontier labs and enterprise platforms to emerging startups reshaping entire industries, The Deep View: Conversations podcast interviews the brightest minds and the most influential leaders in AI.

Jason Hiner: All right, Todd Earwood, welcome to The Deep View Conversations podcast.

Todd Earwood: Yeah man, good to be here.

Jason Hiner: Appreciate it. You and I are here in San Francisco, even though we're not from San Francisco.

Todd Earwood: No.

Jason Hiner: We're both based in Louisville, Kentucky.

Todd Earwood: That's right.

Jason Hiner: And have been for a long time. I've known you for a long time. I've mentioned you on this podcast before. In fact, when I had Rob May on, I said, 'Hey, I think it was Todd that introduced us.' Todd had been telling me for a while, 'You need to talk to Rob about various things.' So we've had Rob on the podcast. Glad that you are here. You were just on my panel at The AI Conference on AI transformation. I said, I talk to smart people every day, all day, and for AI transformation, there were two people. I was like, these are the two smartest people. It was you and Claire Southey, who are the people I've talked to in 2026 that have the best stories about how AI is really being used in the real world. More and more, especially as we got into the second half of 2026, it's just happening in the real world. I was telling you that I'm at parties, or dinner parties. I'm old enough that I don't go to parties anymore. Even at these events, I don't really go to the parties.

Todd Earwood: That's funny.

Jason Hiner: But when I have dinner with normal people who aren't in technology, I don't really mention AI because it's there enough. And now, the last couple of months, people have started saying, 'Don't you do something with AI?' And they want to tell me their stories: 'Here's what we're doing. Here's what we're doing.' It's wild. But you are working with mid-market. You have this history. You've worked 11 years investing in AI, before people knew what AI was.

Todd Earwood: That's right.

Jason Hiner: Except for if they see Terminator.

Todd Earwood: That's right.

Jason Hiner: That's the only thing they knew.

Todd Earwood: That's right.

Jason Hiner: And now you've been, the last couple of years, working at Betra Works. You're the CEO of Betra Works, working with mid-market companies, helping them figure out what's going on with AI. I would love to start there. What made you say, 'You know what? I'm not as interested right now in just focusing on investing. I want to talk to real people and see how they're using technology'? Because you have a long history of technology too. I would love for us to get that on the record, hear about your journey with that.

Todd Earwood: Sure. I think two reasons. Number one, on the investing side, what our firm HalfCourt's done is we've always had this approach of having smart people at the table to—how can we [unclear] the whole landscape of where AI is going to be deployed, accepted or adopted, purchased and integrated? By doing that, we had to look at academia. We had to look at government. One of the gaps over time was ultimately, okay, now it's becoming saturated. Early on, being very early on the investing side, it was different. But the impetus for me was I was interested and curious: I'm seeing companies that are not getting traction, getting the market to adopt or buy their solution. That bothered me. And secondarily, I had a family friend who leads 15 middle-market CEOs, like a mastermind or a Vistage group.

Jason Hiner: Yeah.

Todd Earwood: And so he said, 'Hey, I've got this group of CEOs that's AI curious.' He said, 'They're not scared. I want you to come talk to them about how to apply AI in an organization.' I said, 'That's not what I do.' He's like, 'Ah, but I've heard you speak. You could do it.' I spent a lot of time preparing for them. When I did, I found joy in figuring it out. And B was, I'm always about making something applicable. So I tried to walk them through, here's how to think about where to spot spots, here's how to spot where AI could be helpful. One of the things I do, I take this exercise, this framework of evaluating your job and your tasks, and these CEOs just stared at me. Finally, one of them whispered and said, 'We're not really close to the work anymore. We don't even know how it gets done.' And in the middle market, you're big enough.

Jason Hiner: Yeah.

Todd Earwood: You're not enterprise, but you're big enough where there are layers of management.

Jason Hiner: Yeah.

Todd Earwood: And you're talking minimum tens of millions, typically north of $100 million in revenue. That was an alarming thing for me. But that exercise, I found joy in, number one. Number two was I went, okay, there are people who are trying to figure—this was 14 months ago.

Jason Hiner: To timestamp that. OK.

Todd Earwood: It was the summer of '25. And so that led me to, okay, one of the CEOs grabbed me and was like, 'Hey'—and he's fast growth for middle market.

Jason Hiner: Yeah.

Todd Earwood: He's like, I'm not going to be left behind on this. Help me figure this out. And I go again, 'I only did this because—this is not what I do.'

Jason Hiner: Yeah. Yeah.

Todd Earwood: I'm investing and writing checks into companies. And he pestered me. So I got under the hood of that company, and he's on a good growth trajectory. That gave me a lot of conviction: this long history of tech, layered with investing and seeing the market and what it's been adopting, is very applicable to what these folks are trying to figure out. And their businesses are not fragile. So that's how I got here. I really enjoy it now. It's something I find great joy in, and our success rate's been through the roof.

Jason Hiner: How many companies have you talked to over the past 14 months?

Todd Earwood: My measurement is instead of companies, I've done this with 1200 leaders and executives.

Jason Hiner: Okay.

Todd Earwood: And in 12 months.

Jason Hiner: Okay.

Todd Earwood: So it has been all face to face, nothing virtual.

Jason Hiner: Yes. Yes.

Todd Earwood: And it's been now in every time zone in North America, so it's not just in Louisville. But I would say, industry-wise, I think it's 20-plus industries. And then 19, to answer your direct question. I think 19 companies have brought a team to me and sat just their team alone. In some rooms, it might be a hodgepodge of teams or organizations, but there are 19 companies that have gone deep and said, 'Hey, I'm like John was. I'm not going to be left behind.' Yeah.

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Todd Earwood: Inevitably.

Jason Hiner: And talk to us about those.

Todd Earwood: There's only three ways you can be successful with AI. And that is number one, with my background, my last software company was a data integration platform. We sold that in 23. And so I'm convicted on that side of like the data layer has to be intact.

Jason Hiner: Yeah.

Todd Earwood: To really have scalable AI. That's not what middle market and most people should be looking for anyways. But the first thing I say is, 'Hey, if you want to get your tech stack integrated and we go to the data layer first, you can have great AI.' Number two is if you have a specific workflow that you've actually outlined one to X, every micro step, then we can go in and pinpoint where AI should be a handoff. Where should it be an automation? We could do that. Almost no one actually has that.

Jason Hiner: OK.

Todd Earwood: And number three is what I want you to do: let's talk about how to think about AI and your work and your job. If you start there, the light bulbs come on. You start to build momentum. Momentum spreads from individual to team, team to division, division to org. I found that bottom-up approach is the best way to do it, and it's been wildly successful.

Jason Hiner: So you get these leaders in a room and you figure out who's got a problem that we could use AI to solve, right? That's the sense of it.

Todd Earwood: Before I get to the problem, I set the table. There's so much hype and misinformation.

Jason Hiner: Yeah.

Todd Earwood: First thing I do is I play this game of Dr. [unclear].

Jason Hiner: That's right.

Todd Earwood: Well, I try to disarm them by saying, hey, first of all, you've been using AI in different forms for years. And I show them different elements of what machine learning did for us.

Jason Hiner: Yeah.

Todd Earwood: And the benefits on the consumer product side.

Jason Hiner: OK.

Todd Earwood: And then I go, 'Hey, let's just talk about fact or fiction.' I have discussions around what is true and not true. Inevitably they say things wrong that I get to explain: 'That's actually not how AI works. That's not true.' Everything from privacy and guardrails to, 'What does it know about me?' and those kinds of things. You table set there and you go, okay, great. The problem is it's happening so fast, everyone feels behind. It's the number one message they say.

Jason Hiner: OK.

Todd Earwood: Is, 'I feel behind.' And I go, no—and you asked this onstage—it's early. We're good. Then I go into, now that we know we have to adapt, which is what you said onstage, I want to show you how to adopt. In order to adopt, we start at the individual level first. I teach you some fundamentals about spotting where AI—the shape of a task and a project looks like, because it doesn't work for everything. It's not great at everything, especially if you're not technical. So let's get low-hanging fruit. That's my game. Get momentum and go.

Jason Hiner: Yeah. Now I have to apologize, because I realize that when we were onstage, I didn't give you a chance to talk about your book, which is Adapt & Adopt. So talk about that now. All this work you've been doing, you actually put into a book, because people want—we can get into this—people want a playbook. How do I do it? To your credit, you don't just give them a playbook. You give them a framework for how to think about it.

Todd Earwood: That's right.

Jason Hiner: And it's a framework. It is not a formula.

Todd Earwood: Yeah. I warn people it's a thinking book. So if you don't want to use your brain and you just want to push button AI, it's like, sorry, it doesn't work.

Jason Hiner: There are other books for that.

Todd Earwood: There are other books for that and they don't work either, by the way. That's right.

Jason Hiner: Exactly.

Todd Earwood: Spoiler alert. They don't work.

Jason Hiner: Spoiler alert. Anytime somebody hands you a formula, it's not in your reality. It's not going to work. It's the bottom line.

Todd Earwood: And so I was having—this is almost 18 months ago—I was having dinner at a conference like this afterwards, a nontechnical conference. I was having dinner with a friend who's in the book publishing industry.

Jason Hiner: Okay.

Todd Earwood: I was talking to him about different things I was interested in on the investing side, what I've been seeing, what's being adopted. Some lady was sitting near us on an outdoor patio and said, 'Excuse me, I was eavesdropping. I work for'—and I can't say her company name—'but we're scared, and we don't know what to do. I'm so curious about what you were telling this man.' Like we talked about, you need feedback loops. That's a good feedback loop. She leads HR for a hundred-thousand-person company. She's like, 'Hey, we have insert tool.' So my now book-publishing person says, 'You know that's a book, right?' I was like, 'No, you can't write a book about AI.' He said, 'Yes, you're telling people how to think about it.' So the book is about, A, making the case for it. We do not have a choice. We must adapt, period.

Jason Hiner: Yes.

Todd Earwood: It's not a matter of if. If we accept that it's a when issue, W-H-E-N, when, then we need to talk about the how. The how, I think, is how to think about your work. I've built five skills and 12 frameworks. You can go look through these lenses of how AI can fit in your work, inside your organization. Then I've got some plays of, here's how to go start in these areas if you don't know where to go. So that's the book. It's been a really enjoyable and intellectually challenging project.

Jason Hiner: Oh man. I've written books, and it's a haul. It is a haul.

Todd Earwood: Yeah. I'm glad to be done. It's great. It's awesome. I'm excited. We have six more weeks to be live, and it's awesome.

Jason Hiner: Adapt & Adopt. One of the things I love, and you and I have talked about this, there's a very human thing. We want somebody else to just tell us what to do. I'm willing to do it. Just give me the cheat code and I'll go do it. Myself. As human beings, we have to try to identify and realize, I don't want to do that, because in whatever case, you have to read your own reality.

Todd Earwood: That's right.

Jason Hiner: You have to try to understand it and then think about, what could I use, bring in, start learning? Then create a cycle of learning where I take that back and I go, okay, what did I learn? What do my next steps look like? But that work is hard. People often just don't want to have to do that mental work. But in whatever phase of life you are or whatever thing you're doing, that's where you create value, and that's where you find value and meaning. That's a hard thing. It's bigger than AI. I love it. When we were talking about this one time, you were talking about your dad.

Todd Earwood: Oh yeah.

Jason Hiner: And you're saying that you got this a little bit from your dad and the way your dad approaches things in life.

Todd Earwood: Absolutely. He has this belief, right? He's a retired minister and then started a Baptist seminary, teaching people in ministry, how to train them. He's not tech averse, but I wouldn't even say he's tech enabled. He just wrote a book, and he didn't even think about AI. I'm like, 'Hey, why don't we have AI brainstorm some imagery for your book?' There's some tables and diagram work. It's pretty foreign to him. But I think you're right, specifically, people do want it easy. I said this onstage. I poll people a lot during my workshops: 'What are you seeing? What have you tried?' When I ask them, 'What's the best thing you've seen about AI?' it's 70% personal. It's 30% work. And so it's just the good. There's no bad. The good part is people are finding ways that AI can help them through all walks of life.

Jason Hiner: Yeah.

Todd Earwood: And that's the part that I kind of tried to turn my dad's brain on too. It's like, Hey, dad, I can just have AI try this, right? On some things.

Jason Hiner: Yeah.

Todd Earwood: And the second thing is like, when we carry that into the workplace, it becomes more complicated because now if there's a policy, what does that look like? And candidly for this audience, Copilot, I'm not betting against Copilot and Gemini.

Jason Hiner: Okay.

Todd Earwood: I'm not.

Jason Hiner: Okay.

Todd Earwood: They sit on the data. They know everything about you and the IT folks are not going to, it's hard to flip teams.

Jason Hiner: That's right.

Todd Earwood: From one to the other. So if you want to dip your toe into AI—and this may be a style thing—I don't care what the T's and C's say on their LLM. It's sitting alongside you. You've already given them the data. Sorry. They know all your email. They know SharePoint. They know Google Drive. They know everything about you. So what I tell people is, fine, start there. The challenge is there are certain things that Copilot today, specifically, and Gemini aren't that great at. If you've seen at home that one of the frontier models can do something amazing, and then you go, 'Hold on, but I have to do this janky thing,' I think that's the rub some larger orgs are having to deal with.

Jason Hiner: For now.

Todd Earwood: For now. They'll get there. Don't bet against them.

Jason Hiner: Yeah.

Todd Earwood: Don't bet against them.

Jason Hiner: I think it's true. It's funny. I was having this conversation with an organization last night, and it comes down to trust, right? Like everything else. Again, it's a lesson bigger than just tech and AI, in life. A lot of things come down to trust. I would love to hear a little bit about one of these companies. You and I talked about an athletics company.

Todd Earwood: Oh yeah.

Jason Hiner: And that they came to you and they had a very surprising outcome. From your seminar.

Todd Earwood: That's right.

Jason Hiner: And, I love this example. So I would love for you to talk a little bit about how a very unexpected person on a team found the win in AI.

Todd Earwood: So they, so there's two great stories there. Number one, the one I'll reference yours first. Okay. Is they heard me speak. It was the audience of 1300 people.

Jason Hiner: Okay.

Todd Earwood: And my leading any group of 1300 people through any exercise of thought is hard.

Jason Hiner: Yeah.

Todd Earwood: But someone in the crowd, this lady Tiff, runs leadership and development for this university athletic department. She reached out and said, 'Hey, our leader believes we should know this. My job is to bring skills to the table. Can you help?' I said, 'Oh, I have this framework. I've got a set of frameworks. I can bring it to you.' So I did. The two key points I've not told you: one is, I asked the leader, 'What does success look like?' He said, 'I've got smart people. Just help them find where it can help them.'

Jason Hiner: Okay.

Todd Earwood: 'Let them do their work.' I said, 'Okay. Interesting.' So I told the group, 'Hey, my success rate is a hundred percent.' So now I have the boss saying, 'We're going to do this.' Don't screw this up for me. We're going to find it.

Jason Hiner: I want to be part of it. He brought them in on the deal.

Todd Earwood: Hey, do not break my streak, because every organization that's come in, every one of them, I say, finds it. You're going to go find it. You see if you can find where AI can help them. So theirs was a sales rep. They have a CRO. They have a VP of sales. They have layers of sales, and none of those people found it. It was a sales rep who understood—for some reason, the light bulb in his head, as he's told me, came on—that, 'Oh, CRM is limiting my options that I can sell to. What if I merge CRM data with third-party data sets?' He had AI brainstorm what that might be, and that's how he found it. That's what he did. He brainstormed, A, what would a third-party data set look like? B, help me merge them, because I'm not technical. He could barely spell CSV. He integrated that, but then he went out and had personalized emails, because I showed them the fundamentals and how you could do that. They sold six figures' worth of sports tickets, athletics tickets, in three days after walking out of that door. So that was a big one. The other one is a manufacturer in Buffalo, New York, almost identical situation. You're going to see the pattern here. The leader says, 'I'm either not going to be left behind,' or, 'I need to arm my people with this,' one of the two. Those are usually drivers. Same person was like, 'I'm not going to be left behind.' So, okay, I've got this framework. Here's what it is. I do the workshop. He said, 'Okay, great. We're going to do it.' I came in. They're a manufacturer: an Oracle back-end system of record, Oracle—it may have been NetSuite—front-end CRM, right? So they're spending real money.

Jason Hiner: Yeah.

Todd Earwood: Real money.

Jason Hiner: That's expensive stuff.

Todd Earwood: On enterprise tools, and they're middle market. But one thing I do in how to find or spot where AI could help them—a non-college educated worker in the warehouse.

Jason Hiner: Okay.

Todd Earwood: Was the person that was looking at their workflows. He kind of, again, light bulb came on and like everybody, we live in some spreadsheet.

Jason Hiner: Yep.

Todd Earwood: And no matter what systems we have, we export to a spreadsheet and humans do things. Theirs was the gray sheet, and it's an Excel spreadsheet. A, it's not gray. B, no one could even tell me why it was called the gray sheet, but it's called the gray sheet, and they've had it for 22 years.

Jason Hiner: What?

Todd Earwood: It's now taken a form of a spreadsheet. It used to be some other paper form.

Jason Hiner: Sure.

Todd Earwood: So now it's in this. But despite spending hundreds of thousands of dollars on tools, the humans have to get their work done with the gray sheet. This non-college-educated employee cracked the code with AI: here's how we can eliminate the dependency on this thing. Now it's unlocked all these new workflows that are better, saving them time and actually making them more money.

Jason Hiner: So there was a lot of really valuable data trapped in that gray sheet.

Todd Earwood: Oh yeah.

Jason Hiner: And so by unlocking that.

Todd Earwood: And all the micro steps, because I actually spoke to that person. I was like, how did you do this? What does it look like? And he was like, well, listen, like the bosses, the leaders don't even know what we do with it.

Jason Hiner: Sure.

Todd Earwood: 'There are these eight steps we have to do before I even get to the gray sheet.' The pain was acute enough for him to go, it would be great. So the light bulb for me, I shifted that into, you know what I'm going to do? Let's allow everyone to start complaining about their jobs. What do you do? And so I give them the shape of tasks that AI is good for.

Jason Hiner: Not just this company, but now you do everybody.

Todd Earwood: Everybody.

Jason Hiner: Everybody.

Todd Earwood: Let's just start complaining. Like everybody, because here's the thing. If you let humans complain.

Jason Hiner: Yeah.

Todd Earwood: I'm like, 'Leaders, no judgment. Let them say it.' We let them get out all the BS work they have. That was a great one, because the CEO was like, 'I would have bet all the money in the world in my company on who could have picked it.' There's nothing wrong with this individual. He's just not technically adept.

Jason Hiner: Sure.

Todd Earwood: He doesn't even work on a computer.

Jason Hiner: Sure.

Todd Earwood: That's what he does. His job.

Jason Hiner: Yeah.

Todd Earwood: He works in the warehouse.

Jason Hiner: Yeah.

Todd Earwood: But his brain, whatever. So it's fun to find those. The takeaway, Jason, is one, leaders are very bad at predicting who inside their organizations are going to be good at this. They're very bad.

Jason Hiner: Interesting. Interesting.

Todd Earwood: Universally bad. I've got two more examples for that too.

Jason Hiner: Okay.

Todd Earwood: And secondarily, they're too far from the work.

Jason Hiner: Yeah.

Todd Earwood: So if they're the ones driving the strategy, we're almost setting ourselves up to fail.

Jason Hiner: That makes perfect sense. I love it. Let AI find the most BS workflows in your company and fix them.

Todd Earwood: Yes. That's exactly right. And then I start with one task. I would pick a task, not a workflow.

Jason Hiner: Okay.

Todd Earwood: That's a task. What is that? Something you have to do.

Jason Hiner: Yeah.

Todd Earwood: And then I give them the shape of, if it looks and smells like this—and I've refined and refined—think about these eight verbs. If you have to do one of these activities, and this is the verb—search, update, write, whatever it is—that unlocks the brain to go, 'Oh yeah, I got that. I have to update the report 72 times.' That's the unlock to get the humans to go, 'Yes, I do that.' Okay, great. Now we've found a few ideas. Then I give them a framework, a lightweight green light, red light, whether AI should attack it or not.

Jason Hiner: And people love it.

Todd Earwood: People love it. And they've already identified something they don't like to do.

Jason Hiner: Yeah.

Todd Earwood: And the humans are great at that. They're more motivated by eliminating the pain than the gain.

Jason Hiner: That's true. And ultimately humans will get on the side of AI. I feel like, look, I had this really crappy thing and the AI helped me get rid of something that just is so bad and crappy every day and I can use it to fix it.

Todd Earwood: That's exactly right. It's fun.

Jason Hiner: That's pretty rewarding.

Todd Earwood: Oh, it's great.

Jason Hiner: It's great.

Todd Earwood: One more thing. If I can—

Jason Hiner: Do it.

Todd Earwood: So this company does not want me to say who they are. They don't want to say the industry. I don't know why they're so, I do know why, but I think it's silly, but I know what I can tell you about the story because it's so compelling.

Jason Hiner: Okay.

Todd Earwood: They're one of the organizations. Got them in a room, same edict. CEO's like, 'Not going to be left behind.' Okay, great. I tell them, 'Your job is to go find it and report back, and make it six figures or more.' That's the impact. It needs to be six figures. Make it material. Otherwise—and I point to the leaders—they're not going to care. It's got to be there. There's a line for the size companies. Sure enough, he calls me and says, 'Hey, we found it.' Awesome. He tells me the process. Great. I said, 'Who was it?' Because again, I know they're not good at picking. He describes this person. I said, 'Where were they sitting in the room?' He said, 'They're over here.' I said, 'No. This person, their body language, they did not want to be in the room. They were not interested. How in the world did that person find it?' He said, 'Because you unlocked their brain to, there's something that could eliminate these parts of their job they don't like.' They like their job, but we all have parts of our job we don't like. The light bulb for that person was, 'You mean I can?' By the way, this is the oldest person inside the organization, in age, not necessarily by status in the company. You have this, 'Oh, well, there are certain types of people who are better at this than others.' No, that's just hard to model. What is true is if you find a way to activate their brain and give them the shape of a task, and give them a framework of red light, green light, it turns out almost anybody can find it, is what I'm learning.

Jason Hiner: Okay.

Todd Earwood: That was very compelling for me because, as a facilitator, speaker, whatever, they gave the bad vibes. They were not interested. They weren't even taking notes. I give them workbooks; they weren't even taking notes. But for some reason, what was compelling for that person was, 'Oh, I can reduce the friction in my job.' That was the motivator to help that person find it.

Jason Hiner: And that would have been the last person in the room that you thought.

Todd Earwood: Literally the last, like I need to meet that person again and have like some questions because bad vibes. And now like that whole organization is doing all kinds of things. And one more fun part.

Jason Hiner: Yeah.

Todd Earwood: They hired two interns.

Jason Hiner: Okay.

Todd Earwood: Oh, this is last summer. Oh, we're going to, we have two college interns. They're going to help us with AI. And I was like, Oh, okay. How's that going? He was like, 'I don't know.' I don't know. We got two interns. They're pretty smart.

Jason Hiner: Like you can tell everybody we're working on it.

Todd Earwood: Companies are trying to attack this. It's a very interesting contrast: he hired youth, marginal gain. You enable the senior person who's very seasoned in their career, and they figured it out. Wild. Hard to predict. Matter of fact, executives cannot predict. I'm convicted of that too. They cannot predict who inside their company is going to be the one that drives it.

Jason Hiner: Unreal.

Todd Earwood: That's fun.

Jason Hiner: Unreal. That's cool. That's great. That's why I wanted to have you on the panel. These stories are amazing. It is happening in the real world, and it doesn't hit the headlines very often. It doesn't end up on podcasts. So I was really excited to do it. All right, I want to pivot a little bit and talk about AI, because you've been an AI investor from 11 years ago. When you tell people you're an AI investor, they're like, 'Are you investing in IBM? What are you doing?' They thought of AI and they thought of Terminator, right? Or I, Robot. They didn't really know what it was. What made you decide, 'Hey, this is something we need to start learning a lot more about'?

Todd Earwood: Well, you had Rob on the podcast. He invests with me. Rob actually came to me 13 years ago and was like, 'Hey, go read this paper,' which is what Rob's been doing with me for 25 years. 'Here's this research paper of how a computer can think like a human brain.' And I did not read it. Then he did what he does. He says, 'This is one I want you to read.' Okay, I read it. We had an interesting discussion about it. So that planted the seed.

Jason Hiner: Okay.

Todd Earwood: And then Rob took a neuroscience class for fun at MIT, a night class, at the time.

Jason Hiner: And I love it.

Todd Earwood: It was talking about AI. He was telling me about that. Both of us had had transactions as operators. He said, 'Hey, we should join forces together. We could go invest in companies.' I was like, 'This is terrible. No, let's not do that.' Eventually I said, 'Well, if we do, we need to have an area of focus.'

Jason Hiner: Okay.

Todd Earwood: We knew we had a strong network out here on both coasts. We have strong networks. We'd raised money and done all kinds of interesting things in all the tech hubs. So we knew we had a good network, and we care about entrepreneurs. We felt good about that. But as we went through them, crypto was quickly moved off the table. That was the time, right? We moved that off the table. In 2015, we're having this discussion, and I was like, okay, we have to focus on something. We thought SaaS was going to change. We'd both been in SaaS, and we landed on AI. I said, 'Well, this is a good venture bet, because if it could be'—that's what you want in venture. If it can be transformative, that's what you need for the business model to work. Well, this could be.

Jason Hiner: If it works, it's going to be really transformative.

Todd Earwood: So that's the [unclear] of how we got there.

Jason Hiner: Okay.

Todd Earwood: And then it became our model of go to market was going to the firms that we'd raise money from or even pitch and said, Hey, this is artificial intelligence. Tech VCs even then knew about it.

Jason Hiner: Yeah.

Todd Earwood: I said, 'You're not going to know how to assess it. We are going to build an incredible technical bench.' And, by the way, Rob's hardware engineering background, given everything else that happened, where we knew it was going to go with AI, that was helpful. So we said, 'Hey, just bring them to us. Don't filter. Bring them to us.' We started getting great, what they would call deal flow or lead flow, looking at companies. That's how we started. We were early, but that's how we got to AI.

Jason Hiner: And then you've invested in over a hundred companies.

Todd Earwood: Invested in over a hundred companies. We came out of the gate hot. We had advice from three key, well-known tech investors. One of the pieces of advice was, 'If you want to find deals, write checks.' There are a lot of people who do not write checks. That's a trick that people don't know about. Investors say, 'I'm an investor,' and they haven't written a check in three years. This one individual was saying, 'Hey, if you write checks, the market will find you.'

Jason Hiner: Okay.

Todd Earwood: We doubled down by leveraging our network. Everybody says they're founder friendly, but we're going to write checks. So we came out of the gate hot by writing checks.

Jason Hiner: Which means you're going to invest in a bunch of companies.

Todd Earwood: Thank you.

Jason Hiner: Yeah, you're going to deploy capital.

Todd Earwood: We're going to write—

Jason Hiner: Not just take a bunch of meetings.

Todd Earwood: That's correct. We're actually going to write checks. Oh, that sounds good. And because we're first timers at doing this, we also told our investors who are putting in money, the LPs in our fund, 'Oh, and by the way, we're going to be terrible at this. So if you want to lose your money, give it to us, because we don't even know what we're doing. We're entrepreneurs, but we do know tech. We've been studying this for a while, and it's going to happen. If it does, there are going to be great gains, but it's not going to work.' And then 100% of the people we told that story to gave us money. They were like, 'Well, that's great. I love that. That's the profile.' Yeah, that's the profile. So that's what got us going. And we did. The joke I tell now is it was almost a Noah's Ark approach of AI investing. We have two of everything. I've got two martech AI companies, two HR, five legal tech. We spread that around, heavy on infrastructure. We really still believe, a lot of conviction, that will be the most—if not, that will be transformative. So really, that's how we got in. It's been really great. But the role you play as an investor is wildly different from an operator. There's a different relationship you have, because I hear nothing but great ideas. No one's ever come with a bad idea. It's big, and it's going to be transformative. Then filtering that out becomes the challenge. We see 30 deals a day, and 30 people are going to come to us. Now being here is just going to be worse. You're going to get—

Jason Hiner: Sorry about that.

Todd Earwood: No, it's great. The business in me loves it. We both have been in technology for—I love it. It is amazing to see what people can come up with. You just have to be aligned with, well, what is your thesis? Now we have pretty refined theses that block out most all the AI world. It's just too big.

Jason Hiner: Yeah, it's so there's been so much capital deployed in AI over the past like two years. I've never seen anything like it.

Todd Earwood: Well, here's my take on that. The nontechnical investors have the same pressures from their investors as the leaders in the business world: 'What are you doing about AI?'

Jason Hiner: Exactly.

Todd Earwood: Well, where's AI, and how's it going to affect their portfolio? Now you've got nontechnical finance people who are still the largest audience in investing, the finance people.

Jason Hiner: Yeah.

Todd Earwood: We have both sat as operating partners and venture partners in these other firms. A lot of these people, what you don't know is they're not technical. They do not know the tech. So we have delineated ourselves by saying, 'Hey, when everybody walking by can claim they have built AI, you won't get it past us.' So we immediately built the deep bench.

Jason Hiner: So you know how to filter.

Todd Earwood: Oh yeah, we filter that so easily.

Jason Hiner: Yeah. No, it makes a lot of sense. All right, I want to ask you about not relocating to one of the coasts, because this is something you and I both have in common. We've spent plenty of time on airplanes over the last couple of decades. Many of our peers that we grew up in tech with in Louisville have left. You and I are two of the last ones standing, but also found a way that felt like we didn't have to. We could get on a plane, on the phone, on a Zoom. I would love to ask you because there's the you and I of it, but there are also a lot of people feeling this pull right now. San Francisco rents are just insane. New York also insane. New York just passed San Francisco in terms of number of tech workers.

Todd Earwood: That's right.

Jason Hiner: There's this re-migration pattern. For those folks who are feeling the pull, like, oh, they have to be there. And look, there are plenty of VCs that tell them, 'You can't do it in Austin or Louisville or Chicago or Atlanta,' or wherever. But you're somebody who has contacts everywhere. You do seminars now. You talk to leaders everywhere. But you haven't gotten up and relocated to do it. I would love your perspective on that, because I think a lot of people are facing that choice right now and feeling that pull, like, 'Oh, in order to make it, I have to do that.'

Todd Earwood: Yeah, I've felt that pull multiple times. I think proximity helps. I do think it's a definite advantage. I think you need to pick the game you want to play.

Jason Hiner: Yeah.

Todd Earwood: And B, from the investment standpoint, if you're needing to raise money, I do think COVID shuffled the deck on that.

Jason Hiner: OK.

Todd Earwood: Because when you couldn't, now you could take pitches virtually. That was wild at first, right? And even for us, investors to put money in our funds, we could do it on Zoom. We'd never thought about doing that.

Jason Hiner: Wow.

Todd Earwood: Ever. It would be like, oh, you're going to give us money? Get on a plane, go talk to you.

Jason Hiner: Yeah.

Todd Earwood: So A, I would say COVID shuffled the deck on that. B, as an entrepreneur, I had a lot of funds out here that would not write checks when my company was small.

Jason Hiner: OK.

Todd Earwood: Less proof points. So I think the earlier the technology or the company, the more challenging that is. Okay.

Jason Hiner: Fair.

Todd Earwood: I think that's very different when it comes to if you want to work in technology and not be an operator or an entrepreneur. In Louisville, there's the guy who runs the Facebook ads engineering team.

Jason Hiner: Oh yeah.

Todd Earwood: And I don't think he's 35, and he's living in Louisville.

Jason Hiner: Yeah.

Todd Earwood: I think remote work changed that, right? But I believe that you don't have to move unless proximity matters and you want to employ a bunch of people to sit in a room together. Some people still have that.

Jason Hiner: That's true.

Todd Earwood: I have portfolio CEOs who have really strong feelings on that. I took my last company remote because of circumstances of key people's spouses moving or whatever. I was like, what am I doing? That opened my mind. That was 2017. So I went remote.

Jason Hiner: Yeah.

Todd Earwood: Early on. So I don't think you have to move. I do think proximity really helps a lot in certain cases. Can you tap into the talent pool? On a startup level, as an investor, I would go, how are you going to go recruit people? That said, I don't think about geography anymore as a factor of evaluating you as an entrepreneur. It doesn't even come up.

Jason Hiner: OK.

Todd Earwood: I don't even know. At some point I would say to you on Zoom, 'Oh, where are you calling from today?'

Jason Hiner: Yeah.

Todd Earwood: Because I don't know. I'm looking at your deck, and I'm looking at whoever referred you to me, and some analyst has already looked at it for me. They've screened it. So it's not even a factor.

Jason Hiner: It's like a third fourth level sort of thing.

Todd Earwood: It's not a thing.

Jason Hiner: Whereas it used to be like one or two.

Todd Earwood: I had people say, when I was a founder, 'Hey, Todd, sounds great. I'm not going to go do a board meeting in Louisville.' I would go, 'I'll just come to New York. I'll just come to the Bay.' They were like, 'This is not going to work.' So that was a thing back then.

Jason Hiner: Yeah.

Todd Earwood: That has changed. Is it easier to raise money in certain markets than others? Yes. Must you be there? I would argue no, you don't have to be, unless there are certain circumstances. There are certain cities where it's really great to build a company.

Jason Hiner: Sure.

Todd Earwood: There are a lot of other variables in that too. Talent being the key one.

Jason Hiner: So don't do it because of FOMO. Do it intentionally like I need to do X.

Todd Earwood: That's right.

Jason Hiner: And so it makes more sense for me to do X, or I can't do that, or I can't find a way to do it. If you don't want to move, see if you've tried to find a way that you don't have to. If you get to the point where, in order to do a thing, you specifically need to be pulled there, don't feel like you have to leave.

Todd Earwood: That's right. And look, one time I even ran an experiment. I came out here for four weeks. I was in Menlo Park. I was in Oakland. I was in the city. I can't remember what the fourth one was. But I ran a test.

Jason Hiner: OK.

Todd Earwood: My takeaway was my advantage was I've got a large network. I've been building this network for so long that people will take meetings with me. Before I ever had the checkbook to write investment checks, they would take meetings with me because I've been building that network. That is my other advantage too. If you're not someone who naturally builds a network, some of that may help you.

Jason Hiner: Right. OK.

Todd Earwood: But for me, I've been doing that. I've been getting on planes forever. I think that's how I would frame up that decision.

Jason Hiner: Hey everybody, thanks for listening to this episode. Quick note and then we'll get you back to the conversation. We love bringing you this content every week. We're always trying to figure out how we can deliver you the most value to help you understand how AI is transforming business and transforming the world. If you're enjoying the show, there's an easy way for you to give a little value back and help others learn about the show as well. If you're on Apple podcasts or Spotify, drop us a rating and leave us a review. And if you're on YouTube, hit like, subscribe or leave us a comment. That's it. It only takes a minute, but it's a huge help. So thanks in advance for pitching in. And now back to the show. All right. I'm going to ask you the same two questions that I end the podcast with everybody.

Todd Earwood: Okay.

Jason Hiner: The first one is what's the AI tool that you're using right now that you wish more people knew about?

Todd Earwood: So the interesting thing is there are two questions people ask me above everything else when I do the training. Number one is typically around safety or privacy.

Jason Hiner: Okay.

Todd Earwood: The second question is, what tools should I use? People want the tool. 'Just tell me the tools.' I've had to tell people, I will give you my index of what I use or what my tool stack looks like across everything I do. And you shouldn't listen to it, because it changes too fast.

Jason Hiner: Sure.

Todd Earwood: Yeah. So look, man, I still think there's a couple. Everybody knows, they should know by now, Wispr Flow is the number one thing I use every single day.

Jason Hiner: Okay.

Todd Earwood: I use it across everything I do. Everyone does know that. I'm not really using a lot of the sneaky tools anymore, because the audience that I care about—I've got this crazy network of startups that I'm never going to not see the new thing.

Jason Hiner: Yeah.

Todd Earwood: So I don't really have to watch that anymore.

Jason Hiner: Sure.

Todd Earwood: And then read The Deep View.

Jason Hiner: So you read The Deep View.

Todd Earwood: I'm already seeing, you're going to cover it for me. If you don't cover it for me, I've got someone pitching us. I don't do the new thing very often anymore, as much as I'm very use-case focused. I have several things I do all the time. I'm very dependent upon my meeting recorder.

Jason Hiner: This is the one I was going to tell you, because more than anybody I know right now, you're like, 'I've got to have it.' It's my baseline of stuff that I need to figure stuff out.

Todd Earwood: Okay. Think about how I've framed up this whole thing about how AI can help people. It starts with workflows and taking tasks. For me, I'm in meetings. A lot of us are. That is the easiest unlock for you and your professional career. There are times now—I've done this with you with coffee—I'm like, 'Do you mind if I record this?' Because I have workflows built out and a repository now. In my last company we sold, I gave the buyers of the company 200 hours of recordings. I was like, 'Here, you want diligence on my company? Query this.' They weren't even thinking AI. Just think about that. I still think the meeting recorder is the number one thing, but Wispr Flow. I'll answer the question. I'm sorry. The tool I use for teams, if you need to share recordings around teams, I'm going to tell you to go to Avoma. No one uses that. A-V-O-M-A. Aditya built that business. I looked at investing in it when it first came out. I really like it. It's great for teams.

Jason Hiner: Okay.

Todd Earwood: If it's not teams, you're going to go Granola or Fathom. Everybody loves Granola because they have an ad budget, so they got it in front of everybody.

Jason Hiner: That's right.

Todd Earwood: But I think because Superhuman and Fathom are now connected, because Fathom got bought by them, are they going to eat into Granola's work because the tech crowd is on Superhuman? I think you're going to see Fathom explode because they're going to be in that bubble.

Jason Hiner: I still use Otter.

Todd Earwood: Yeah. Well, that's a little surprising. But people like Otter. People like Fireflies.

Jason Hiner: That's right.

Todd Earwood: I like Avoma for teams. I like Fathom or Granola.

Jason Hiner: These are all pretty good, though. If you're in a lot of meetings, or you're in important meetings, it's good. I remember the one time we had coffee and we went through a bunch of things, and then your meeting thing—

Todd Earwood: No, I think someone called me, and then it interrupted the voicemail and it broke the connection.

Jason Hiner: It broke the connection.

Todd Earwood: It said, 'Do you want to restart?' And I wasn't paying attention. I was very upset about that. So yes, that's the number one tool I use there above everything else. I use Wispr Flow. I'm a complete addict. They do a great job of telling me—I don't even know if they're telling the truth—but I'm in the top 2% of all users. I love it. Being on a plane, I'm so loud. When I was flying out here, I was like, 'How am I going to work?'

Jason Hiner: I know.

Todd Earwood: What am I going to touch a keyboard?

Jason Hiner: It's funny. Sabrina and I on our team, we talk about this. When we aren't in a place where we can talk to the thing, it gets sort of painful. Yeah.

Todd Earwood: I did it on the plane. I was leaning in the corner to talk. That's the rule. I think meeting recorders and voice dictation is where it's at.

Jason Hiner: Okay.

Todd Earwood: For everybody.

Jason Hiner: All right. Last one is, there was this promise: when we have AI, it's going to do all the grunt work for us. It's going to take care of the tasks, just like you talked about, the dirty tasks we don't like. And we're going to be able to touch grass more, get out here, go to baseball games, whatever.

Todd Earwood: That's right.

Jason Hiner: And in fact, everybody I know now who is using AI the most, because they can move faster on some things, they're spending more time working. So it's becoming really important to think about, how do you optimize your time for maximum leverage? This is what I love to ask leaders: what's your best tip for leaders out there in this AI age? How do you optimize your time for maximum leverage?

Todd Earwood: I talk to two different groups of people now. The leaders, in some ways you can imagine, are engaging with me. The people who are working now with me, there's a drive from there. The top down is only the acknowledgment of, I need to figure this out.

Jason Hiner: Yeah.

Todd Earwood: What I've been advocating for them, and what I'm doing in my life, is, if you think about the assistant analogy, I'm using the digital assistant to go alongside me and say, 'I'm setting the tone for you.' Of course, I built a tool for this. You can go get it right now on betraworks.com. I built a tool, a context card, and say, 'Here, if you answer these 20 questions, you will get a much better experience with AI.' Then I've gone to 200 questions now, and gone very deep into, this is what I care about. Keep me aware. I know I'm susceptible to these things. Look at my calendar and start sending me alerts when you see. If you were to train AI—it's not hard anymore either, by the way, not for the average leader—but you need to tell AI, 'I want to do X.' For me, it's, 'These are my goals. This is what I care about. This is what I'm susceptible to. Please help me protect myself and my time by sweeping my calendar constantly.' Right before we started, someone messaged me and asked me something. I don't go to Google Calendar anymore. I go to a specific area that I've set aside in Claude. Then I say, 'I'm being asked this. How should I evaluate this request?' That has been supremely helpful for me. It's not about conflicts. It's about, 'Todd, you said you wanted to accomplish X. That is a tough week for you, man. Are you sure you want to do that?'

Jason Hiner: Got you.

Todd Earwood: That, I think, has been a crazy unlock for me.

Jason Hiner: Wow.

Todd Earwood: And it's been helpful. And I built a lot of tools because, again, I got this large data set.

Jason Hiner: Yeah.

Todd Earwood: I've been polling people. I've been face to face, dealing with the body language and their reactions, talking through their challenges and seeing what people do. There are a lot of parents doing this on the personal side. They're like, 'Oh, the school dumps a bunch of stuff on us.' What's the first thing you do? Take a picture, give it to AI and go, 'Can we accomplish this? What are we going to do? What are the conflicts in the family?' I think there are benefits all around on the personal side too. But that's where I would start. Always tell it why it's important.

Jason Hiner: Yep.

Todd Earwood: Give it the framework, what you're susceptible to. Then look over my shoulder and protect me. And then have the guts to say no. You say yes to everything, right? Have the guts to say, 'I can't do it there.' AI is better at flagging things for me than I'm flagging myself.

Jason Hiner: Great advice.

Todd Earwood: I have one thing for you.

Jason Hiner: Hit me.

Todd Earwood: And you can cut this if you need to.

Jason Hiner: Okay.

Todd Earwood: I do one thing on podcasts.

Jason Hiner: Okay. So you can cut this where you're going to end it.

Todd Earwood: I want to trade. I'll give you my time to talk. I want you to look at the camera and tell Jack and Lila Earwood, my children. I want you to tell them, when they encounter something challenging—

Jason Hiner: Yeah.

Todd Earwood: What is your recommendation of how to get past this challenging part? Because everything I'm actually doing in my life is for my children.

Jason Hiner: I love it.

Todd Earwood: So I want you to say, 'Jack and Lila Earwood, when you encounter something challenging, here's my advice to you of how you're going to get past it.'

Jason Hiner: Yeah. Jack and Lila, hey, good to send you a message. Love your dad. Since he asked this, we're going to keep this in the podcast. The thing that I have learned that I would love to share is that when challenging things happen in life, one of our most human things is to react to them. One of the best things we can do, and one of the things that I learned from some really great people, is to try to do the opposite. Instead of speeding up, actually slow down. Take a breath. Take a minute. Think about people in your life that you love and care about and who have given you good advice. Think about, what would they say? What would they tell me in this moment? I'm sure you get a lot of that, because you have great people around you.

Todd Earwood: Thank you.

Jason Hiner: I love that. Thanks for being here.

Todd Earwood: Appreciate it so much. Appreciate it, Jason.