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Without Charging a Fee, Dave Parker Helped Founders Raise $400 Million

Dave Parker, founder of Trajectory, shares lessons from five startups, two shutdowns, a bankruptcy, and cancer, and how he now helps founders prepare to exit their companies well.
Host: Anthony Codispoti
Published: Sep 11, 2026
Without Charging a Fee, Dave Parker Helped Founders Raise $400 Million

🎙️ From Five Startups to One Playbook: Dave Parker's Journey Building Trajectory

In this episode, Dave Parker, founder and chair of Trajectory, shares lessons from founding five companies, selling three, and closing two, all while surviving a personal bankruptcy and two family cancer diagnoses along the way. Dave opens up about the emotional isolation of founder life, the moment his own attorney reminded him whose side he was really on, and why he's now building a coaching network to help other founders exit well.

✨ Key Insights You'll Learn:

  • Started his first company two weeks before his wife's cancer diagnosis

  • Grew License Online from zero to $32 million before selling to a billion-dollar rival

  • Shut down a hardware startup after realizing it had no real problem to solve

  • Shut down a second startup after discovering its cost to sell exceeded its revenue

  • Identified 14 revenue models used across the tech industry

  • Built the Founder Cohort Program, helping 375 companies raise $400 million with no fee

  • Wrote Trajectory Startup, named a top HubSpot business book of 2021

  • Survived a 2008 personal bankruptcy and two family cancer journeys

  • Uses AI daily to draft product requirement documents and financial forecasts

  • Is writing Trajectory Exit to help founders navigate selling their companies

🌟 Dave's Key Mentors:

  • His Wife: Partner through cancer, bankruptcy, and every founder decision along the way

  • Brad Feld: Wrote the foreword to his first book and modeled openness about mental health

  • Rich Barton: His “power to the people” framework shaped how Dave evaluates startup ideas

  • His Former Boss at Excel Data: Supported his leap into entrepreneurship and remains a close friend

👉 Hear how a five-time founder who survived bankruptcy and cancer is now building a coaching network to help other entrepreneurs exit their life's work well.

Listen to the full episode here

Transcript

Anthony Codispoti (00:00)

Welcome to another edition of the Inspired Stories Podcast, where leaders share their experiences so we can learn from their successes and be inspired by how they've overcome adversity. As you listen today, let one idea shape what you do next. My name is Anthony Cotispodti, and today's guest has founded five technology companies. He sold three of them and closed two. Both halves of that record shape how he now advises other founders.

He started out in sales in the mid-90s, launched his first company in 1997, and spent the next three decades moving between the founder's chair, the boardroom, and the executive suite. Along the way, he helped scale a global startup organization to more than 1,250 events across 120 countries before it was acquired by Techstars. He's Dave Parker.

Founder and chair of Trajectory, a founder support ecosystem that guides entrepreneurs from idea validation through scale up and exit. He's the author of Trajectory Startup, named number one of HubSpot's best business books of 2021. He's also served as CEO of Entrepreneurs Organization, CEO of CodeFellows, and a board member for companies including Classmates.com and Guidant Financial.

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Add, that's right, add nine hundred dollars per employee per year to their bottom line. Results vary, but gains like that can change how a business is valued. Addbackbenefits.com. Okay, back to our guest today, the founder and CEO of get trajectory.com, Dave Parker. Thanks for making the time to share your story today.

Dave Parker (02:36)

Thanks for the invitation. It's good to be here.

Anthony Codispoti (02:39)

So

Dave, let's go back to 97. You left a sales director role at Excel Data to start license online. Walk me through the week you decided to do that. What was going through your head?

Dave Parker (02:52)

I'll I'll give you the extension and into kind of the three weeks because it was kind of a wild the upfront piece of it was I noticed the big gap in the Microsoft ecosystem. We were a large systems integrator in Washington State, and we'd gone from about 200 employees to about 650 employees. And every month my Microsoft rep would come to me and say, Hey, how much software you guys gonna sell? And every month I'd say, We don't sell software. We do services. And then we lost this contract to a a little company.

Who was doing a desktop migration? There was this little coffee company in Seattle, some of you may heard of. And we didn't sell hardware and we didn't sell software, we only did services. So we lost this big desktop migration to another company because we didn't sell software. And so I kicked it around with the the folks that I work for at the time, and and they're like, We're we don't sell software, there's no margins in it, it's a it's not a great business. We are in the services business. So I went back to my Microsoft rep and I'm like, how many.

People are there out there like us that just do services and don't do software. And he's like, hmm, most of them. And I'm like, tell me more. So come to find out, there was a huge systems integrator work across the US. And nobody wanted to sell Microsoft software because it was kind of complex. So the first product we bought was a configuration tool that helped you figure out: am I buying the right software? I need server software, I need desktop software, I need right there were pools and packages, and it was just super complex. So we were the first ones to build.

a configuration tool that made that easy. And the company went from

Anthony Codispoti (04:20)

It made it

easy to analyze all the different options. This is probably the best path for you.

Dave Parker (04:24)

Yeah. So think about this as the time was

we were going from you know AOL floppy drives to to CDs, right? And we were the first digital license delivery platform. So you could actually configure and buy 250 seats of something, but not get 250 CDs. And that was the innovation behind it was we could actually do the configuration and the license delivery. So that company grew from zero to 32 million in sales in four years.

Happened to be around the tech bubble, happened to be just post 9-11. So it wasn't a great time to be owning a company, but it was it was a great time to to start a company and grow it. But going back to the start, two weeks after I started the company, I had left my job. and my wife was diagnosed with Hodgkin's disease cancer. And much to our surprise, we went through the process of like, should I go back to my job or not? My boss, my former boss was great, dear, dear friend to this day. And

And he's like, you know, we didn't want you to leave. We'd love to have you back. And my wife and I went through the process of like, well, this was a good decision before circumstances changed. Have the circumstances changed enough that we should rethink the decision? And much to her credit, the answer was, no, the circumstances haven't changed that much that we should rethink the decision. So that started us down this entrepreneur, crazy entrepreneur journey that we've been on ever since. And we're still together. I look I think about the stuff we've been through and think there's

probably

things you would probably not wish for anybody. But when you look back on it, you think, yeah, those things all also kept us together. Because we got to a point where it's like, you know, we disagree about something. Is anybody gonna die? No. But I guess it's gonna be okay. Like we'll figure it out, right? In the grand scheme of things, it just gives you perspective.

Anthony Codispoti (06:11)

You've got a different yardstick now after having gone through something like that.

Dave Parker (06:15)

Totally the case, right? Because it because doing a startup is hard. I mean, the odds of success are low. You know, I think if you, if you did it, if you thought about it reasonably, you would go drive a bus, right? Because you're like, the bus shows up every day, I get paid every two weeks. This is so much easier. But the opportunity for, you know, founders are are strange in that we're we're driven by an idea. And that idea hopefully is a good idea, but

When I'm around folks who are like, it's hey, the market's this is good a market, bad market is a good time to start a startup. I'm like, founders are driven and compelled by an idea. They're they don't really look around at the circumstances that they're facing and decide to do it or not do it based on that. They decide to do it based on being compelled. And that's what drives most of us as founders.

Anthony Codispoti (07:01)

Yeah. I couldn't agree more having been in that seat myself many times. and having started in economic downturns before. right? When when you've got an idea and there's a a fire that's lit under you, you just gotta go for it. Yeah.

Dave Parker (07:15)

You can't not do it. Right. I mean, for

most of us as founders, you just can't not do it. You're you're you're it's the thing that's obsessing you. Now, whether that's good or bad is a different topic, by the way, but it is what it is.

Anthony Codispoti (07:24)

So this

that we're just making observations here. This is how this

Dave Parker (07:30)

not judging.

Anthony Codispoti (07:31)

is how we're fueled. Yeah. So this business that you started, license online, your innovation sounds like it was twofold. It was configurating this this tool that would allow you and the client to determine, you know, should they have these digital licenses, should they do a different thing, you know, basically like because the buying decision was really complex.

Like you could put in like all the different criteria for this client and then it spits out a recommendation on this is the path that's better.

Dave Parker (08:01)

Yeah. And the other thing we did that was unique, Anthony, was you had this massive channel out there that were delivering services and predominantly making money for delivering services. And they they didn't, they weren't experts in licensing. They didn't want to have a licensing expert on staff. So we were, in essence, their licensing expert and we would configure stuff for them and get them the right product and software, which would help them sell more product to their customer ultimately. But keep in mind the services business and the product business are really different.

And

the challenge there was, you know, in the early days was recruiting those channel partners. So getting people to say like, cause they were t traditionally like, we don't do that, right? I'm like, well, what if it was easy? Right. So yeah, so we grew the comp the company and then in 2002 we sold it to a company called Cinex Information Systems, which is a a big public company that's then turned around and bought tech data. But we were you had a thirty million

32 million dollar company, our next biggest competitor was a billion two. And those are the guys we sold to. And then the two bigger ones were 13 and 15 billion, respectively. So you know, it's a little bit like dancing with gorillas. You're not through till he is. And Microsoft was our biggest vendor. So at one point, you know, it was definitely Microsoft were pushing us the direction of hey, go get go get acquired, and you know, nudging a particular direction.

I I wouldn't say those were the great partnership, Sacha Nadela enlightened partnership years of Microsoft as a point of reference, but it is what it is. And I and I think that's goes gets back to the I started the idea because it was a problem that I noticed that needed to be fixed. Knowing what I know now about unit economics and where the money is made, it's probably not a business I would start again. I can say quite confidently it's not it's not.

Anthony Codispoti (09:44)

Even going back to what the circumstances were like back then, you

Dave Parker (09:48)

Knowing what I know now, the answer is the unit economics were tough, right? And so you have things like today I recognize them as DSO and DPO, so day payment outstanding and day sales outstanding. And these are just it's just a KPI that you you pay attention to in in business because as we grew the business, growth capital is difficult for a startup company. And that was all well and good until you're doing three million dollars a month in revenue, and you have to pay your vendors in 30 days, but you're

Your customers pay you in 42 days, that 12 day float is not something you can fund with equity. So as the business grew, you would eat more capital, right? So it was always a business that was a difficult business to do well in, unless you were well capitalized, which explains why big companies pay slow instead of paying quickly, because they're they're minimizing that DSO DPO gap. Right. So all stuff you look at now and go like, hmm, knowing what I know now.

there's better businesses to start. And I think that's true for

Anthony Codispoti (10:47)

W

Dave Parker (10:47)

most of us as founders.

Anthony Codispoti (10:49)

what would you have done differently back then?

Dave Parker (10:52)

I I think the the relationship that we had with we we kinda wedged ourselves in to become a d Microsoft's first distribute new distributor in fifteen years and we did it based on momentum. But it was just a hard business to compete with because you had, like I said, multi billion dollar companies who were competing with. And they could literally just weigh you out. Right. That was kind of their that was kind of their gig was, Hey, let's just we'll we'll drop our prices and cut their margins and try to move them out of the business. And that that was what happened at a at

one level. So stuff you you have to be aware of what's going on in the market conditions. It just goes with the territory.

Anthony Codispoti (11:29)

So you started five companies, you sold three of them, closed two of them down. tell me about the two that you closed down. What happened there, what went wrong, any lessons learned?

Dave Parker (11:41)

For

sure. So one of them was after I sold license online, and we did okay with that. It wasn't a great exit, right? But one of my investors was a company out of Japan, third largest company in Japan, Goldman Sui Company. And they had been working on a technology, and they reached out to me and said, Hey, you were in our portfolio, we'd love to have you come on and be the founding CEO of a new hardware company. And I think you know, there's a little bit of naive

Well,

not a little bit, or I think, I guess. There's a lot naive about startup founders in in the market conditions. And this was one where this was a hardware problem looking, this was a hardware product looking for a problem. And the idea was interesting. And they had spent a bunch of time on research and development. And I kind of leaned into their RD experience and said, well, there must be something here that I can go find the problem that it needs to go answer.

So I think of myself in retrospect a little bit more of a go to market person. Now I'm more of a product person, but in the early days I was more focused on go to market and sales marketing. And what we noticed was that it's a product, but it wasn't, you know, it was it was a basically a thumb drive that had a a USB stick that had a fingerprint sensor on it and a processor on board. So the question is what can you use? What problem can you fix? So we tried HIPAA, we tried security, we tried, and we finally got to a point where we're like, there there's not a

There's not a market for this. There's not a problem this is solving. And I think the big takeaway for me with that, and I wrote about it in Trajectory Startup, was you have to pivot around the problem, not pivot around the product. Right. And for people who fall in love with the product, they're like, the product is brilliant and I love it. And it's and the answer is that's not what you need to fix. What you need to fix is you need to pivot around the problem and become acutely aware of the problem and how you're gonna solve that problem, not the product first.

So that was the first big one.

Anthony Codispoti (13:29)

So it sounds like

sorry, David, it sounds like in this case somebody had the idea like, ooh, we can put this fingerprint technology onto a USB drive, put a little processor. We could combine these kind of existing technology things

Dave Parker (13:42)

Totally.

Anthony Codispoti (13:43)

and create something that nobody had before. Very cool, without having sort of an underlying problem that they were solving towards.

Dave Parker (13:50)

Totally

the case. Right. And it was in in essence well funded because it was it well backed, right? But at the same time, the market research hadn't been done other than the technology research.

Anthony Codispoti (14:03)

Okay. And so that company ultimately did not pan out. You

Dave Parker (14:08)

Yeah,

ultimately I helped shut that company down because which was funny in some ways, because when I went back and I'm like, I don't think there's there's not a there's not a market here. And I had a board member tell me, I think you're just being negative. And I'm like, I've been accused of lots of things, but being negative is never one of the things I've been accused of. Overly optimistic, maybe? for sure. But you know, being negative has never been one of the things I've been accused of.

Anthony Codispoti (14:32)

Okay, so walk us through the other business that we shut down.

Dave Parker (14:35)

The the other business came from a problem I was working on as a dad, right? Is I was a Scoutmaster, I was a Little League umpire, and every year we do a fundraiser for our events. And every year I'd have a different set of parents asking the same vendors, you know, same Mexican restaurant, the same blah, blah, blah, hey, can you donate to this event? And I'm like, that's something software can fix. So the idea was hey, could you do a donation automation software? Could you make it easy for

a

a company to donate stuff or respond to these donation requests. And this was an interesting Anthony because you could build the product, but what we found out was the cost to sell the product was way more than the cost of building the product. So the unit economics and go to market were inverted. So give you an example, so if I went to a restaurant and he said, hey, drop a button on your website, let

point people that have a donation request to the website. And then you can fit you can manage it like a LinkedIn request, right? You want, you want a dozen cupcakes for this event for for the the final of the of Girl Scouts for the year, right? The problem was is the customer might pay $20 a month for the product, but it cost you, you know, if you look at my lifetime value in 12 months, $240 is what I'd make in revenue, but it cost me $500 in sales expense to sell it.

All because you're doing a product that no one has ever done before, and there's no keywords for donation automation software in Google. So the big lesson in that one was, yeah, you can in the innovation economy, there's there's two sets of businesses that usually get started. Services businesses. You're selling a product somebody else sells, right? So there's no product market fit risk. You're you're buying accounting services. The question is, who are you buying them from? Will you buy them from me? In this case,

Anthony Codispoti (16:31)

The market's already

demonstrated that it needs this service. It's just a question of hey, now can I can I be the one that they choose?

Dave Parker (16:38)

Totally. Right. So there's there's no service product fit risk, right? It's it's the question of do I will I build up buy it from you or will I buy it from somebody else? But with product, product market fit risk is I'm doing this new product, no one's ever done it before. Does anybody care? Right. So the and but founders are so passionate and they're like, but I'm passionate about it. I'm like, passion is table stakes. You have to be passionate, right? But just because you're passionate doesn't mean you're right.

So in that case, we'd have to hire a direct sales team to do outbound sales to small businesses who, in their top three list of things they're focused on doing today, donation automation software is not one of those things. Right. So we built a product that could be a category killer. The problem was is the cost of selling it was more expensive than the cost of building it. And that happens to a lot of startups in the product space.

Anthony Codispoti (17:33)

So talk to me about the two other businesses that you built and had successful exits from.

Dave Parker (17:38)

So

did a consulting company that we grew to about 65, 85 folks, turned around and sold those shares to my partner. And then the other other company was focused on the HR space and helping to gr make business think of it as a business process around HR and how do we make it simpler for HR services companies. That one wasn't a great exit, but it was like,

Somebody who found it and went, yeah, we really want this. And it was more of an aqua hire than it was a real exit. But it was nice to have it as a quote unquote an exit anyway versus having to close it down. So when I look at all those things together, the pieces that you put together are like some businesses are worth building and growing because they're disproportionately large ideas. And then some businesses are a problem that you're solving, but the problem you're solving isn't that big. Like in the case of the small business one.

Are there millions of small businesses out in the US? Millions. Are they easy to sell to? Absolutely not. Right? So that ended up kind of influencing the first book about a third of trajectory startup is about how do startups make money and how do you price them and what are the unit economics? So the challenge with that is just because you have an idea, I hope your product is unique.

But how you make money is never unique. And there's 14 revenue models used in tech. So

Anthony Codispoti (19:04)

Fourteen.

Dave Parker (19:05)

that's it. Now, one of them is a combination. So you can put together subscription plus services or like AWS is a metered service business. But to give you an example, if you and I do a services company and we do a million dollars in revenue, that company's probably worth about a million dollars. But if you and I do a subscription revenue company,

and we do a million in revenue, that company's probably worth six to eight million dollars because we shift from trailing 12 revenue to future 12 revenue. So that singular fix by itself increases your multiple because now you're talking about future revenue less churn. So

Anthony Codispoti (19:43)

So why does that flip happen? Why does it go from looking at trailing to future?

Dave Parker (19:47)

Typically the services businesses is transactional, right? So the question is who's going to sell that customer, that repeat business, or who how am I going to customers than I had last year? If I had 10 customers last year, I need 12 or 13 customers this year. A subscription business says I had 10 customers last year, so I start the year with 10 customers. Now I'm increasing 12 or 13 customers. So I'm growing the business 20 or 30%. So less churn, right? So there's some customers will leave.

But even if you look at like the guys who do my, you know, insect and and and service for my house, right? They no longer charge me every time they come out. They charge me every month and come out every quarter, right? Because the revenue model then flips to forward 12 versus trailing twelve and it flips to less churn. So you'll see private equity companies are now buying up those companies on a multiple of future revenue versus

Versus a multiple of trailing revenue. So just an economic shift, but a big benefit that founders need to understand.

Anthony Codispoti (20:53)

And

so tell us some of the other things folks get from reading your first book.

Dave Parker (20:59)

a couple things that were not well covered. So we did the book. My MVP, if you will, of the book was I did a program called Six Month Startup. And we did it three times as a workshop. And every month we would walk people through content. They'd get to meet with their mentors. but if they didn't do the work, they didn't get a talk to the mentors. So they'd go around the table first over dinner and say, here's what I learned and here's what I did. And then the table would prioritize who got to talk to the mentors for feedback.

So we eliminated the folks who like, I'm gonna talk about the same thing I talked about last month. I just haven't done anything because I have a job and I'm not really serious about a startup. So three things that came out of the workshops. One was what makes a good idea? So I actually wrote up 11 frameworks for ideas. So one example, for example, is how Rich Barton thinks about ideas. So Rich founded Expedia and spun it out of Microsoft, then founded Zilla.

So, Rich's perspective was this concept of power to the people, which is taking opaque data sets and making them accessible to people. So, real estate and travel as an example. So, that's just one example of the 11 outlined in the book of like what makes a good idea. How do I know that this is a good idea or not? And that actually was a question that somebody asked after the first or second session the first time we did it. And they're like,

Hey, you're kind of, you know, this was really interesting and you're kind of entertaining, but I don't have an idea. What do I do? And I'm thinking, how did you even get in here? Like we only market this to startup founders, right? The second thing was pricing. So one of the things that happens with pricing for new startups is we know the product isn't really great. It's not quite ready for prime time. so we price it low and cheap instead of quality in within what's called pricing anchors.

So one of the chapters is about pricing and how to think about pricing and how to systematically test pricing. And the last thing was the around the 14 revenue models, the third thing was we tracked 2,564 companies over a five-year longitudinal study to look at how they made money. And then by the way, that correlates to a list of 175 companies that are publicly traded and what's their multiple of revenue. It's not the only factor in getting to your evaluation, but it is a factor in getting to evaluation.

Anthony Codispoti (23:16)

How do you test pricing?

Dave Parker (23:18)

So test testing pricing is really starts with price anchors and what are the customers used to spending. So for example, if you're in the enterprise space and somebody's spending $200,000 a year on Salesforce, and you come in at a product of $2,000 a year, it's gonna lack credibility. So price anchors sets a range for products that customers are used to paying. So think about it as a particular car class. You could call it a Honda, a quarter or a Toyota Camry. Every car in that car class ranges from low to high.

Right with variation in that range. They don't get way lower, they don't get way higher. So that's a price anchor. And that's true in your product as you sell your product as well. But when you're a founder and just getting started, you're like, we're gonna go in cheap. But cheap may be the wrong answer, right? From a credibility standpoint, the customer may look at it and say, like, I that doesn't sound like it's credible. Right. So pricing then becomes a routine that you look at every quarter with a pricing committee.

So you have your salesperson, your marketing person, your product person, and you. And by the way, in the early days, that could be all you, right? But you systematically b go back and look at what are the competitors doing, how the competitors priced it. Go back and use the Wayback Machine, which is the Internet Archive, and look at how your your competitors have priced things in the past. And now with AI, you can do it so much easier. But the idea is if you're trying to fill a specific niche around pricing, you need to know what your competitive landscape goes to.

And

then the testing happens one of two ways. Low fidelity, right? I'm doing sales calls. I have two price sheets, right? If my call goes well with Anthony, I'm gonna give him the good the big price sheet. If the call's not going well, I'm gonna give him the cheaper price sheet, and I'm gonna get his reaction. And I have to be comfortable waiting for a reaction, right? So if you have high fidelity and I have traffic I can buy on the website, I can buy Google AdWords, or I can buy buy traffic through ads and Instagram, more consumer than B2B.

Then I can do A-B testing on landing pages and see which one converts better. But early stage for most founders, it's low fidelity. And I'm really trying to get feedback from customer surveys and customer sales calls. I just have to be comfortable with the fact that I'm going to present a price and I need to wait for a reaction. And a lot of people get really uncomfortable with that.

Anthony Codispoti (25:36)

uncomfortable just because there's that silence. You and I are talking either face to face or on Zoom. I've given you a price of twenty thousand dollars and I wanna keep talking because it's uncomfortable to just sit there

Dave Parker (25:49)

And wait. Because the age old the age old thing is still right. Whoever talks after that is the one who buys. And all too often it's the founder who buys their own product.

Anthony Codispoti (26:00)

And so w how do you coach somebody in that situation?

Dave Parker (26:03)

It's really about the freak the number of calls you're making, right? If you only have one sales call, then you're gonna take whatever price you get. If you have optionality and more sales calls, that becomes a lot easier because now I can test the is the value proposition resonating. So think of think about how do I, if you're a founder, your big takeaway from this one is I have a value proposition, it's very narrow to this specific ideal customer profile. What happens a lot in the marketing side of this is I have this very broad.

value proposition to a very broad ideal set of customer profiles. So consequently it doesn't resonate to anybody. Versus I have a very narrow popul or very narrow ideal customer profile and that value proposition maps to that specific I ICP with a price. That's what I want to go test. I don't want to test it generally because I'm not going to get any good data. It has to be very specific.

Anthony Codispoti (26:56)

You know, your talk about price anchoring reminded me of a fun conversation I had years ago with the former CEO of Nespresso, who gave me a very similar kind of example. He says, you know, early days of figuring out how to charge for these Nespresso pods, like what are we going to compare ourselves to? He's like, if we compare ourselves to the cost of

Making it at home by yourself, with a you know little stove top device that existed, you know, packing in the the grounds yourself. W we're a very expensive option then. He says, But in our marketing back in the early days, we positioned ourselves as a comparison to what you might pay if you went to a a local coffee shop and and got a shut of espresso there. In that case, we're a very inexpensive option and the quality is comparable.

Dave Parker (27:50)

Totally the case.

So w what's interesting about price anchoring is because founders fall in love with their own products rather than the problem, they tend to be like, isn't this really awesome? And the answer is the the customer doesn't care. The customer cares what it will do for you. Right. So the age old, I'm I'm I'm not buying a drill bit, I'm buying a hole. And the reason I'm buying a hole is because I need to hang something up, right? Or I need to do something else with it. But the drill bit's incidental. And because founders fall in love with product instead of the problem.

we end up positioning that pricing in the wrong direction. And that happens a lot in early, especially in early stage product companies.

Anthony Codispoti (28:27)

So

I'm looking at LinkedIn here, I see two different companies that share the trajectory name. There's trajectory media and then there's trajectory network. Tell me the what each of these does.

Dave Parker (28:40)

Well, when I did the first book, I signed with a publisher who should go nameless. And I realized that I was going to be the publisher the next time because publishers are great at getting new ISBN numbers and on Amazon. But other than that, I'm not sure that selling dead trees is really a great business model. So after that experience, I decided to start Trajectory Media. Trajectory Network then became a parent company for four different brands that sit underneath it.

So, trajectory startup is focused on helping early stage startup companies really validate their idea and understand the process they're going through. Trajectory scale up, and there's a lot of stuff written in the scale up space, by the way, is really focused on how do I scale up the business. And then trajectory exit is focused on how do I help founders exit the company. So while I was the CEO at EO, I had a chance to hang out with Vern Harnish, who started EO and wrote the book Scaling Up. I met the guys from scaling.com.

Gina Wickman wrote the book Traction. And I was like, my gosh, there's a lot written in this category for scaling up. So though I think there's still some gaps around product marketing and scaling up product companies and innovation economy companies, I deferred that, Anthony, to later. And I'm focused on trajectory exit now is the book focused on helping founders exit. And the rationale there was really simple is for most of us as founders, it's our life's work, right? I've

I've taken a risk. I've started a company. I spent seven, 10, 15 years building it or more. And now it's time to sell it. And one of the one of the things that happens frequently is I'll get an inbound call from somebody who's like, hey, we're really interested in your business. Now, I won't call that a one step up from a Nigerian Prince phone call, but it's kind of close, right? The only reason you're getting an unsolicited offer from somebody who's never met you before is because they're going to lowball you.

So it it's this this information asymmetry was the thing that was driving the second book, was focusing on exit and leveling the playing field to make it easier for founders to understand who they're sitting across from, who's probably done it 50 or 100 times, right? From a founder who's like, I fell in love with this business. I've been running it a long time. And so that's that's really the angle in the next piece is really helping them figure out how to exit.

Anthony Codispoti (30:56)

And

this book is available today on Amazon.

Dave Parker (30:58)

It

it gets to the I'll get it out for edit in September and it'll

Anthony Codispoti (31:03)

Okay.

Dave Parker (31:04)

be out in the fall.

Anthony Codispoti (31:05)

Okay, so not too far away. We're recording this in August of 2026, and so within a few months, this should be available. And so in there, folks are gonna have a better idea of hey, if I can't, and can folks hire you for these same kinds of services or

Dave Parker (31:22)

Yeah, so right now

we're doing it as consulting service and we're building out a a network of exited founders who are focused on the book as the framework they coach to. And then we're building a set of AI tools that really help the founder build out their data room and build out their model and understand how how do I track the enterprise value of my company? And am I doing the things today that will really help me impact that enterpr what they call total enterprise value or T E V that help me impact the total enterprise value of the enterprise over time.

So giving example versus just regular coaching, there's a lot of there's thousands of certified coaches out there in the in the ecosystem, right? Whether it's on the EOYPO vistage side or whether on the innovation economy side, there's not a lot of coaches. And one of the things I noticed consistently, there's not a lot of coaches who prepare you to exit. So for example, I don't necessarily need to build a new product, right? If indeed,

I'm gonna sell the company in two years and the product's not gonna be ready for three years. So you probably shouldn't have put that on your roadmap, right? Or you shouldn't invest a lot of money in it. So the the thing that we focus on is what are the things I can do in the near term that gained me the best enterprise value. And then I don't know if you've seen the the process of having a letter of intent. So what happens? You can either build a value before the letter of intent or you can defend your value after the letter of intent. So the defense process comes in what's called a quality of

earnings report. So we do what's called a sell side QOE or quality of earnings, and we look at all the stuff that the buyer's going to ding you on in price. Right. So for example, customer concentration is a great one. And if more than 25% of your revenue comes from one single customer, you're likely going to the price of the sale may not change, but the structure is going to change. You're going to push to an earnout to prove that the customer is going to come with you.

So those are things that founders just don't know because they've never done it before. So equalizing leveling the playing field here was really important.

Anthony Codispoti (33:21)

So help me connect the pieces of the puzzle here. We've got the book, we've got the consulting services, and is one kind of feeding into the other because you're talking about with the book you're building this network of exited founders

Dave Parker (33:33)

Coaches.

Anthony Codispoti (33:34)

and how they all fit into this.

Dave Parker (33:37)

Yeah, it it's really taking a model from Gino Wickman's book, Traction. Right. So Gino wrote a book called Traction. It has a three-ring binder they coach the coaches coach to. And there's about 780 implementers worldwide who coach to traction. So the the idea there was like, cause at heart I'm a business model junkie, right? So I mean we we tracked 2,654 companies, how they made money. So I'm always looking at the model, going like, that's unique. How did how'd that one work?

Right. And what you find is business models by themselves, Anthony, aren't aren't defensible. So remember a few years ago when Groupon came out and it was this new business model. Ultimately it was Commerce and Lead Gen, by the way. That's those are two of the 14, delivered in a combination model that was unique. But if you remember what happened at the time, there were literally dozens and dozens of competitors, right? We're just like Groupon, but we're in Seattle instead of Chicago, right? Or we're in Thailand. And the answer was.

Business models by themselves aren't defensible. So it anybody can copy that. So in this case, we're copying a model that's been done sustainably, which is I have a book and that has a framework to coach to. In our case, we have software that's very AI-centric software around how do we prep you for exit. And then a coaching network who's somebody that, you know, selling a company is a very emotional experience, unless you're in private equity, in which case I've got 3x over three years and we need to sell it.

But for most of us as founders, the answer is having somebody to help walk you through that process is important. So today I'm the number one coach. So I'm doing finishing the book and I'm finishing the software and I'm coaching people. But we're bringing on more coaches as we finish the book so we can actually scale that up into a a more sustainable business that could be global.

Anthony Codispoti (35:24)

fascinating. Has anybody taken this same approach outside of your niche and out sort of outside of the niche that EOS has been built into, which is more like the scaling up part of it?

Dave Parker (35:36)

Yeah, the scaling

up folks, there's a lot. so you have scaling.com, which is Dr. Benjamin Harding's book, that he did with Anthony Robbins, did the forward to the book. You have scaling up, which is Vern Harnish's book, you have Gina Wickman's book, you've got Hermosi's hundred million dollar deal book focused on you know, really folks in the the social media category. So there's a ton in the scaling up part of it. But when you cut when it comes to exit, you don't really wanna

Have

your general, your MD be your brain surgeon? You really would rather have somebody who's been there before. So our whole thesis is that that really brings in a network of people who are like, I don't really think of myself as a coach, Anthony. I'm I'm kind of a founder, but I've exited. So if you if I could help another founder exit, that feels like a great opportunity. So that's what we're seeing in the spaces we're recruiting exited founders who've actually done that work, right? Rather than somebody who's

Anthony Codispoti (36:34)

And will these

exited founders that are now representing your program go through your special training or they have kind of a workbook that will take them through your approved steps?

Dave Parker (36:44)

Yeah, they have

a training program that we put them through in orientation, but then the software is really the kicker. Right. So when we when we bring folks in to do the software, we're actually tracking things like so give you give you a couple of examples. So if if if I come into the business and I'm a coach and I'm coaching a roofing company, the data set for transactions in the roofing business are quite robust over the last 20 years, even 30 years. So I can tell you that that company on a multiple of EBITDA.

Is going trade in a band that looks like this. And if you do these six things, you can increase the value of the company. Now, I don't know the roofing business, right? I know innovation economy business. So in the innovation economy, it's slightly different. The formula is based on if I'm I have a friend who sold three companies to Google. None of them had any revenue. How do you calculate the value on that? And the answer is, well, there is a calculation. It's just not based on it's just not based on EBITDA.

Right. So all of these vertical, so that there's a a concept here of the the NIAX code or the NIX code, right, which is the industry code. Each of those industry code has transaction data, but what I can tell you from the initial software is how many transactions in your category happened last quarter and last year. So in that case, you'll get a res a result that says n equals 244. So I know in my category there were 244 transactions in the last 12 months. That's more informative than most founders ever have.

Right as a start. And then telling them what to do to improve the value is is where we take over.

Anthony Codispoti (38:18)

Is part of your secret sauce how you get access to that data?

Dave Parker (38:21)

Some of its subscriptions, some of it's it's funny, most of it's not real time because the data doesn't change fast enough to be to care, right? But yeah, how we ingest the data and from what data sets they come from is definitely part of it. And you know, what's interesting too is some companies want to be judged on a different set of data sets, but that's not what they qualify for. So just having access to the data is it goes back to the Rich Barton example I listed. Power to the People says if I take opaque data sets.

and then make them more accessible, it's a good thing. So I guess it I I guess that one had more influence on me than I knew at the time.

Anthony Codispoti (39:00)

what is DK Parker or is this just sort of an umbrella for the things that you've been doing for a long time?

Dave Parker (39:05)

Yeah,

it's my L L C that I use for investing and angel investing and that sort of thing. So it's the it's the it's the f very small family office.

Anthony Codispoti (39:15)

Got it. Okay, so in the experience that you've had, all the research that you've done, the writing of the books, the different companies that you've worked with, what are some of the most common things you find when you open the hood on a company that thinks it's ready to sell?

Dave Parker (39:32)

the first thing is is dependency on the founder. Right. So the question I always ask in the in the brief survey is could the business run for four weeks without you? And most often the answer to that question is no. So and founders will look at it and say, like, well, it feels like we're kind of stage appropriate. And I'm like, that may be true, but the buyer is still going to ding you on the fact that you it is comp it is dependent on the founder. Right. So

Getting yourself in a position where you can take some time off, advisable anyway, and actually not micromanage the business. Again, your your staff will appreciate it, right? Is super important because the dependency on the founder is one of the big issues. The second one is customer concentration, I mentioned, right, which is I I I have a friend I I play golf with who I g I referred him to a customer some years ago, and that customer is still his single largest customer. And the answer is you need to diversify your customers.

Because if that one customer goes away, it's super expensive. And people be like, well, I think I just think of work with this customer better. But the concept there, at least on the investing side, is what we call the the you know the strike of the pen, right? Somebody sells the business, does something, and you're out, right? So diversification of the business is super important. then we go back and look at a lot of the financial stuff as well, which is quality of earnings, quality balance sheet, all those things. But that's those are more

bigger company stuff where we think of lower mid-market as how do we take somebody and get them to a five million dollar or fifty million dollar valuation from wherever the business is now. And sometimes one of the things we see is people get re-energized about the business too. And that's fine. But there's also a point where it's like it does it go to my kids, right? From an EO perspective, what you had was different countries have different perspectives on multi-generational businesses. And do your kids want the business or not? Right.

that's not a very US centric thing. So what you do with it becomes an important option before you while you have optionality, right? Versus I'm burnt out or I have a health challenge and now I need to think about selling urgently. That's never a good never a good process to step into.

Anthony Codispoti (41:43)

Let's talk about that owner dependency piece. the four-week test that you mentioned is really interesting, right? If you went away for vacation for four weeks, could the business run without you? The answer is no, you've got a problem. So I've been in this seat myself. Lots of friends have as well. You want to start building the team, the infrastructure in place so that it doesn't all rely on you.

But in the midst of all the day-to-day that you have to already do in juggle, it just seems like an overwhelming task.

Dave Parker (42:18)

Totally.

Anthony Codispoti (42:18)

Do you have some advice on how we can sort of break it down into these bite-sized chunks that makes it more manageable?

Dave Parker (42:25)

Well,

it's it starts with operations and just knowing what you're overseeing and what you're micromanaging, right? And there's a little bit of a personal issue there relative to I hey, we're founders, we have control issues at heart, right? So you have to recognize first off this could be an issue for you and you may not like to look in the mirror on the topic, but you have to anyway, because it will dramatically impact the business. Or it could flip the business into an earnout, or it makes what is called a retrade, right? Is you get an offer and then they're like, hmm.

Much dependency on the founder, we're not gonna do the deal. So you have to look honestly in the mirror and say, can I write these operational things down? Great news is you can use Claude to do this. It's upload your org chart, talk about what tasks you want to do, ask Claude to help you right delegate tasks better, and then come up with the KPIs that you want to monitor with the person you're delegating the task to. Right. So usually that control issue has to do with the fact that either I don't know the KPI or the KPI knows so well.

that I'm trying to I'm I'm trying to second guess where the business is going, right? And because that's the way I've grown the business. So you really need to look at it and say, how do I delegate these tasks and how do I put the right KPIs in place so I can measure them so the people who are managing those things can can see them coming with me. And I'm training them how to think about it. Right. And that can be a hard thing because I I there's a risk, right? I I was

had friends who are like, I'm gonna hire interns for that. I'm like, I have to spend so much time training interns that it's not worth hiring the interns. Right. But the same thing is true here is if you've got a good staff on place, or if if you know they're not a good staff, you probably need to upgrade. Which is sometimes it's work that founders are like, it's exhausting, Dave. Why do I have to do that? And I'm like, only if you want to sell. You want to keep micromanaging the business, keep doing what you're doing. Right. But at some point, you gotta you got to move past you.

Anthony Codispoti (44:19)

So I get and I agree with everything you just said, but boy does that still feel daunting. Like give me give me like a first step. I wanna I wanna take a baby step. I just I gotta get my feet wet with this. I need to get some momentum.

Dave Parker (44:32)

So I'm gonna take the KPI that's most important to me, and it may be sales or it may be customer relationships. Let's start with an easy one, which is if I look at my list of customers, because we're gonna ask you for this in the data room, right? Like here's a list of my top 10 customers, here's a list of my top 20 customers. What percentage of customer concentration is set up with that one customer, top five customers, top 10 customers? Who has the relationships with those customers? it's only me.

So now I need to work on, in addition to my one relationship with you, I need to work on who's my person who's gonna have a relationship with your team member. So I'm gonna make a deliberate plan to begin to branch out and build new customer relationships from my side, but also from your side, because it's the it's likely that that's not the only person I need to have contact with. So I'm gonna start with customer relationships, right? Because I need to build a sense of less dependency on me to do that. You don't have to call me, right?

So somebody else may be more responsive than me. Well, but I have your text number. You do. But there's somebody else in your organization who should probably talk to somebody else in my organization at some point. Right. So cut I'd start with customer dependency because it's such a big hook, right, on the exit side.

Anthony Codispoti (45:45)

Hm. I like that. How are you using AI in your work now, Dave?

Dave Parker (45:50)

you know, I it's funny, I'm more technical now than I've ever been, which my former CTO from the the first company was like, Yeah, you're a lot more technical than you used to be. Which for you know, for a guy who has kind of Rayman quality tech skills, I'm like, I it's a great compliment. so when I started doing research for the book, so I've I've used AI to help as my research assistant, and I I tried both Gemini, Claude, and OpenAI. now I'm pretty much down to just Claude.

So that's an interesting exercise. I've written a lot of scripts in Gemini. Like so, data room is a great example of when we onboard a new customer. We send you through the customer form and it creates a Google Drive data room for you with the folders and subfolders that are already outlined. It's a script that Gemini wrote for Gemini to create the data rooms. So I would rather take an hour to do a script for something that takes me 20 minutes.

But then use the script multiple times. Right. So that type of stuff is things that make it really a lot easier to do. The research on the book for sure, competitive analysis, research, all the stuff that you want to do around like what's happening in my market pricing are things that you can do then on a routine basis with AI and come back to those same prompts and use them over and over again. The biggest thing we're using right now is to have Claude help write the product requirement documents.

So I've migrated from kind of a sales and marketing guy by background to a product person over time. So I know what pro what problem I'm trying to solve, right? And back to that focusing in the problem piece. So we have an enterprise value dashboard that we've created. And by the way, all the product requirement documents, I'm like, I'm going through and writing it and then saying to Claude, take all of these requirements and turn them into a PRD, product requirements doc, that I can use a developer to do the

the

connectivity on. So I need single sign-in and I need security and I need a domain subdomain routed. I can do all that stuff, but it's not a great use of my time. So the PRD gives me all the requirements I can hand the developer who can then put all the pieces together. And then I'll come back and and we'll run through and we'll use then Claude to do all the testing around do all these pieces work together or not. Is the

Are the are the pixels in the right places or not? So we use it a lot for PRD and we use a lot for testing. In some cases, I can have it write draft code for me as well and build demos in a product like Netlify. So Netlify is a tool that you can actually write the prompt in Claude, write it for Netlify, or write it for Lovable, and then post the prompt in Lovable or Netlify, and will build a demo app for you. Now, does it go to a database?

Well, it can, right? But you can build a demo super fast. So if you're a product founder and you're thinking about doing a new product or a new idea, you can use Netlify and and and Lovable to build the product, but you need to get good at writing the product requirements document. So we do a lot of that these days. The other thing we're doing is when we onboard a new customer, Anthony, we'll take your last three years of financials. We'll ask you if you have a good Proforma template.

Because one of the things you want to do as you get ready to sell is I want to have a solid forecast and then I track monthly forecast versus actual. So am I am I am I hitting the numbers consistently or not? Because remember, the buyer is underwriting risk at the end of the day. That's all they're doing. So if you show that I'm have a good trajectory for growth and you consistently hit your numbers without re-forecasting every month, that business is super predictable, which means it's more valuable than a business that is not predictable. So

We'll ingest those three years of financials. If you have a good financial model, we'll use it. But if you don't have a good financial model, we'll use AI to build you that pro forma and then start tracking the forecast actual on a monthly basis.

Anthony Codispoti (49:56)

So

a lot of people listening are wondering, am I using the right AI tool? Am I missing out because I'm using ChatGPT versus Claude versus Gemini? And you were using all three at the same time and ultimately decided on Claude. Why? What led you to that?

Dave Parker (50:12)

for my use case

for PRDs, writing software, and testing code, Claude for sure was the most useful, right? Both from what it understood about me and what I was doing with it. And then from a research perspective, Grox pretty good. From a competitive analysis perspective, I like open AI, Gemini's good for s they're they're all

leapfrogging each other. So I you may come back to me in six months and be like, what are you using now? And the answer is, well, I'm using something completely different. I think what you'll find and the the frontier models are interesting because they're they're just leapfrogging each other. So Kimmy is a great example of that. Right. Kimmy's the open source version. We don't really have a great US open source version right now. Open source going to be super competitive in the future, right? Not some people will hear that and go like, well you're supporting the Chinese one. I'm like, that's not not what I said.

open source will be hugely competitive because people can use that open source, download it to do on premise. You know, we in technology we're weird, right? We go, we're we're all exclusively on premise, then we go to all exclusively on the cloud, and now we're going to move back to on premise. And the answer is that's just technology evolution, right? So know that open source will be one of the things that won't go away because as these models get more and more expensive and I want to run

For what's called a rag as an example. So a rag is my own data set. Every time we bring on a new customer, we bring on their data. And if they want to benchmark themselves against other companies, which by the way, we're founders, right? We're competitive. I know my number's cold, but I'm like, am I in the top decile or the bottom decile of my of my group? I don't know. What if you could know? What if instead of a dashboard, this was a scoreboard? And I told you what things you could, what levers you could pull to be in the top decile instead of the bottom decile?

And

for founders, that's really interesting. And that's something AI can do that we've never been able to do in the past. So it fits a what's called a federated data model, right? If if I contribute data, I can benchmark the data. It's not really a big idea, right? Because PayScale has been doing this for years. Right. I contribute a salary information about my job offer. I get back whether that data is good or not. Is this a good job offer or not? The same thing could be true for business, but we've never done it down at the lower market end because it was never

rational to do. We've done it high end, public companies for sure, but this will allow us to actually do a syndicated data set that allows you to say, hey, by the way, n equals 244 transactions and you're in the top decile. Super helpful for founders.

Anthony Codispoti (52:54)

So one of the things that you said just now, Dave, there's been a lot of conversation around this idea of these open source models and being able to host these, like you said, kind of moving from the cloud to bringing it back in house and just the tremendous benefits and and cost savings versus the the frontier models. Are we there yet? Is this is this something we can do now? Or or is okay, what are we waiting on? What's the

Dave Parker (53:20)

Not not yet. Right. I think we're I think we're

there's security we're waiting on, there's infrastructure we're waiting on. you can run OpenClaw on a Mac Mini at your office, right? That's not enterprise grade. Right. It's cool, right? And I'm geeky about all that stuff. But you you still have to get to a point where we're like, have we defined the business processes that we really need to run? Ironically, right, everybody's like, it's gonna lose jobs. I think there's gonna be more service jobs implementing these things.

and on-prem than we've seen it before. Right. So the the jobs will change, right? One of the pictures I have on my wall is of my grandfather's shop and his garage in 1911. He had the first Ford garage in Camus, Washington. And they would ship the parts because 1913 was the assembly line. So in 1911 they would ship the parts of the Model T out to Canvas, Washington, and they would reassemble them. Now, are there as many cowboys

Today, as there were then? No. Do we still have mechanics? Yeah, pretty technical mechanics, actually. So I I don't think we're gonna lose the jobs. I think the jobs are gonna change. And for the folks who decide they love horses more than anything else, I I hope it's a good hobby. Right? But the the idea here is the jobs are gonna change. I don't think they're going away. You know, I'm a bit of a techno optimist anyway, but so discount appropriate.

Anthony Codispoti (54:49)

So

do you think there's a future in which AI can replace what you're doing?

Dave Parker (54:55)

I don't think it replaces the relationship component, which is why we're building it. The sustainable part of our business is the relationship that the coaching network has with you, the founder, to help you walk through this crazy journey of selling your company. Right. And that's an emotional roller coaster. And I ultimately I give you a funny analogy, right? When I sold my first company, so when we still licensed online, my attorney looked at me and said, Hey, we have an LOI.

I want to remind you that I represent the company, not you. Now, me and the company were pretty tightly integrated there for a really long time, right? And he was my thought leader partner. And all of a sudden the music stopped and I lost my chair in musical chairs, and I don't have somebody in my corner. Ultimately, that's the book, right? Is how do I get a coach in my corner who's representing me? Because founders feel like we we went and did this alone, we finally found a network of folks, and now my attorney is.

Representing the company and not me. And that's because, and it's right, right? Because we're two different entities, right? But who represents the founder? How does the founder make sure that's the best deal for them and everybody? Right. We have a fiduciary duty from a board perspective. We need to represent all shareholders equally. But it doesn't mean that it's an at an extreme cost to you as the founder. And in for most startups, the founders have taken second fiddle. They haven't paid themselves market rate, right?

All those things are things that we finally get a payoff when we sell the company and we you just need to be knowledgeable about.

Anthony Codispoti (56:27)

But are these things that AI could eventually do? Be my

Dave Parker (56:32)

Some of them

Anthony Codispoti (56:32)

emotional guide dog through this process and tell me if I'm getting the best deal.

Dave Parker (56:35)

Yeah, I don't think relationships ever

get replaced, right? I mean, I think that's the thing that the human connection, the same reason you do what you do with this, right? The idea that you can hear somebody else's story, and I'm like, we have that shared experience. AI will never have a shared experience. It will reflect back to you what AI is good at. It can give you some great answers to questions as long as you ask it the right question. If you ask the wrong question, it'll still give you back a wrong answer, right?

So yeah, the the human the human condition piece I don't think ever changes. And that makes me happy because we're all in this together. And once you find your tribe, you're like, I'm gonna I'm here to support my tribe.

Anthony Codispoti (57:13)

that.

Dave, what's one of the hardest things you've ever had to go through personally? And what did that teach you?

Dave Parker (57:20)

Yeah, I think as founders the risk factor is really high. Like we we you don't you don't measure risk. So we went through a personal bankruptcy and lost our house in two thousand eight. my wife's a cancer survivor. I'm now a cancer survivor most recently as of seven months ago. though I feel more like a cancer scheduler, by the way. I was it was prostate cancer. So one day you have it, the next day you don't. It wasn't like I went through chemo and radiation like my wife did twenty five years ago. so I I'd say the risk profile is

You know, there's I think there was a normalization in 2008. I wasn't the only one that went through that. It doesn't mean I'm proud of it, right? You you learn more through the challenges than you learn through the successes, I think is true. At the same time, you can't sugarcoat the fact that when you fail, right? Because there's there's a there's something in our culture in the US in particular. Anthony was like, it's not really a failure if you if you learn something from it. I'm like that.

Is such BS. Right? Because if you didn't return investor capital, or if you disappointed somebody, or like it's still you have to embrace both sides of this journey, right? There's gonna be Yeah,

Anthony Codispoti (58:33)

Right. Tell my checking account it wasn't a failure, right?

Dave Parker (58:36)

I mean there's there's highs and lows in this journey, right? So have I been worth millions of dollars and have I lost millions of dollars? Yeah, totally, right?

If I look back on it, would I managed it differently or swung for the fences less or I I don't know that that's a decision you you can make at the time. One, I don't get to I'm a golfer. As much as there's times where I'm like, my God, I wish I had that shot back. You don't get it back.

Anthony Codispoti (59:03)

You don't get mulligans in real life, huh?

Dave Parker (59:04)

There

is none. So the answer is I played it this way. I have the consequences to deal with. Right. But I don't get a sh I don't get it. There's no do-overs. Right.

Anthony Codispoti (59:15)

So it as you think about sort of the emotional roller coaster of your wife's cancer diagnosis, your own, going through those treatments, and sort of juxtapose that against the personal bankruptcy. Contrast and compare for me the coping mechanisms, how you got through those.

Dave Parker (59:35)

Slowly with a bit of depression, a lot of therapy and some chemicals. Not not self-medicated, mind you. Though that happens a lot with founders too. I think there's a I think there's a trade on here that I'm probably indicative of in some ways of that I would just tell founders, therapy is really good. Being in connection with other people is super important. going through depression, right? So Brad Feld wrote the foreword to my first book. Brad's been very open about his

His journey with mental health. I posted a blog post about it one time. I hit the submit button and I thought, Anthony, holy shit, what did I do? Like, I'll never be fundable again. People will look at me differently. It was the most red blog post I ever wrote. Right. And Brad sent me a note, and his one-word email was brave.

I didn't intend for it to be brave. I just want to be helpful. Right. the same thing is true. I posted about the prostate cancer. Why would you take something personal and share that? Well, the answer is it's easy. It's just a freaking blood test, you guys. Just get a blood test. That's all it is. If they catch it early, it's inconsequential. Right. And it's just a blood test. Right. So for good or for bad, I've always kind of been that way of like, this is for

For whatever audience I have, there's things I want to encourage people to go do. Being alone is not one of the things I want to encourage people to go do. Right. So I've seen I've seen too much tragedy along that line. And there's just too much, there's there's too many people out here that want to help and are willing to help if we just know that you're going through a challenge. Has it always been perfect?

Anthony Codispoti (1:01:17)

Yeah.

Dave Parker (1:01:17)

Absolutely not. It's hard. Right? Like I said, driving a bus could be easier, right? You have to worry if you if you hit the stop on time or not.

Right. But for as a founder, the answer is it can be a lonely journey and you just have to make sure you're not in it alone.

Anthony Codispoti (1:01:32)

I love that. Yeah, and Brad Bradfeld was a guest on the show too. Great interview. If folks haven't heard it yet, you can go back and check that one out after you're done listening here with Dave. and I'm so glad that you gave some attention to this because it is such a big thing that so many people in general deal with, but especially founders of businesses, they end up feeling like they're isolated on an island. I hear this story over and over again. I've lived it myself. And you know, you feel like

You have to be the strong one because everybody in your organization, they look to you for guidance, for support. Yeah.

Dave Parker (1:02:07)

County name. Yeah.

Anthony Codispoti (1:02:09)

And so where do you go? What do you do? And for so many folks, the answer

Dave Parker (1:02:11)

Well, I I think that's part of why like

EO and YPO and Vistage have such huge retention rates. Because I I going back to something I said earlier, once you find your tribe, you don't want to leave them. Right. And my I love my sister in law dearly. She's been a teacher and an elementary school teacher for thirty five years plus. What I do and what she do does is completely different from each other, right? So much so that she's like, I don't understand how you do what you do. Like this is kind of crazy. And I'm like, I

It is probably a little crazy. It

Anthony Codispoti (1:02:42)

Yeah.

Dave Parker (1:02:43)

it's a small percentage of the population. But finding people like you is is key to that and building those in investing in those relationships. You have to be willing to be a little bit transparent because if you're not, you're just you're just faking it and you don't that's not what you need. You don't need to fake it. You need to find a community you can plug into.

Anthony Codispoti (1:03:00)

I think that human connection is some of the best medicine that we have. Yeah. And so now, Dave, as you think about the work that you're doing today, what is it that you most want to be remembered for?

Dave Parker (1:03:11)

Well,

I I you know, it's I was in a coffee shop a couple of days ago and I I ran into a guy who went through the six month startup program like five years ago. And he's like, You know, you're the reason I'm an entrepreneur and I was like, I'm I'm sorry. 'Cause you probably could have went to work at Google, great CTO.

My goal when I started the we we do a founder cohort program. My goal when I started that was to support founders in our ecosystem and to the meta goal was to leave the ecosystem better than I found it. Right. And I had a friend say, Hey, seven years, 350 companies, they raised 400 million dollars. I think you've succeeded at it. I'm like, Yeah, but there's a next generation of founders who don't know the ecosystem, right? Who that so that it it never stops. It's it's asking. So we did that.

without fee and without equity for the Washington Tech Industry Association. And 370 companies, 400 million dollars raised. And the answer was, what what should I do? And the answer is pay it forward. There's always somebody you're you're one chapter ahead in the book. You know a little bit more about AI than they do. You know a little bit more about go to market than they have. Just pay it forward. Because it's the thing that if you look at Silicon Valley that Silicon Valley has that no other place in the world has, which is this reinvested capital, this reinvested people, right? There's a

There's an ecosystem of reinvesting in each other versus I sold the company, I bought a boat, and I moved to an island, right? Which is very Seattle, right? but reinvesting in the community is something I don't think I'll ever not do until I can't do it anymore. Right. At some point I'll play more golf, right? But right now it's to chance to reinvest in the community is just a a scale you want to be remembered for was, you know, did we give back to the community or not?

Anthony Codispoti (1:04:59)

Dave, I've just got one more question for you today, but before I ask it, I want to do three quick things for the audience. First of all, anybody who wants to get in touch with Dave, go to the website get trajectory.com. It'll be in the show notes. Two words, super easy. Get trajectory.com. Also, if you're enjoying the show, please take a moment to subscribe wherever you're listening. See, it also sends a signal that helps others discover our podcast. So thank you for taking a quick moment to do that right now.

And as a reminder to all business advisors out there, your clients are bleeding money on health insurance. Do them a favor so big they'll tell their friends about it. Show them how to give their employees access to therapists, doctors, and prescription meds that counterintuitively increases, increases the company's net profits, real gains that can change how business is valued. Learn more about this product from Bain Capital Insurance at adbackbenefits.com.

So Dave, last question for you. A year from now, what is one very specific thing that you hope to be celebrating?

Dave Parker (1:06:04)

Well, September's a big month for us. We're having our first grandchild in September. So it'll be almost a year to his first birthday. And he may actually care about me at that point, Anthony, but I think in the grand perspective of things, you know, it's the first year he's not gonna give to he didn't care about me very much. Grandma will be super excited, but I the legacy you wanna leave in life is to outlive it.

So if you can do that through whatever means you can, whether that's giving back to the community or giving back to your family, I think that's the sadly our perspective is generally limited to our lifetime. When you see our lifetime in context of what else is happening, there is a way to outlive it. So give to those things, they'll pay off a big a big dividend. So that would be a that would be a great marker a year from now.

Anthony Codispoti (1:06:54)

I love that. Dave Parker from Get Trajectory.com. I want to be the first to thank you for sharing both your time and your story with us today. I really appreciate

Dave Parker (1:07:01)

Thank you, Anthony.

Anthony Codispoti (1:07:02)

you being here.

Dave Parker (1:07:03)

You bet.

Anthony Codispoti (1:07:04)

Folks, that's a wrap on another episode of the Inspired Stories Podcast. Thanks for learning with us. And if one thing stood out, put that into action today.

Connect with Dave Parker:

Website: gettrajectory.com