Ep 296: 2 x $10M + Business Exits & How To Overcome Common Entrepreneurial Blockages with Jeff Durso

What is the difference between exiting your business in a rush versus preparing for a grand exit? Hi, I'm Jaryd Krause. I'm the host of the Buying Online Businesses podcast and today I'm speaking with Jeff Durso, who is a serial founder with over 20 launches. He's also excited about $10 million plus businesses and he's number one; he was number 149 in the placement of an Inc. 500 company.

We talked about his wedding business, and he is also the host of Founder Breakthrough's podcast, where he interviews top founders and shares their insights from their entrepreneurial game. Now in this podcast, Jeff and I talk about two businesses that he has exited and what he learned from the first one, how they got to a figure on somebody that wants to acquire it, and how long it took for them to settle that deal, and what happened in between, what he learned with the frustration and the rushingness of trying to exit this business in a way that it didn't just fall through.

Very good things for you to learn and insights from Jeff on what to not do. And then we have another example of him selling his other business, which he actually started with the exit in mind and all the things that took place throughout that period of growing that business to get it to a point where somebody had to come and purchase it. It was too much risk for another business in that space to not purchase it. We also talk about some of the blockages that entrepreneurs have with starting a business, but mostly what are the blockages they have throughout their business in terms of growing and scaling it. We talk about minimal vile product, we talk about product market fit a lot, and there's so much value in this podcast.

Now we do talk about exiting and acquiring. If you're thinking about buying something, don't go away and do it alone. Make sure you get my due diligence framework, as it takes the guesswork out of acquiring an online business, buyingonlinebusiness.com for just free resources.

There'll be a link in the show notes. Now let's dive into the pod. Do you have a website you might want to sell either now or in the future? We have a hungry list of cashed-up and trained-up buyers that want to buy your content website. If you have a site making over $300 per month and want to sell it, head to buyingonlinebusinesses.co to just sell your business or email us at [email protected] because we will likely have a buyer. Details are in the description.

Hello, Jeff. Welcome to the Buying Online Businesses podcast.

Hey, thanks for having me. Looking forward to this chat.

You've done a lot in your career and I want to dig into a bunch of things you've done in terms of startups and selling. But firstly, congratulations on what you've achieved so far. Thanks, and I appreciate that. So how did you get into startups? Where did this come about?

So I think it's funny that when I was younger and we had an Apple II computer, it was kind of the beginning of that whole computer revolution. And what I saw is all the different gaming companies then, and a lot of these have gone on to become like million-dollar game companies. They were basically like a bunch of people in their kitchen that would like to take Ziploc bags, put the floppy disk in them, and send it out. And then I'd watch these game companies very quickly turn into these successful companies and continue to grow after that.

So that was sort of the first model that I saw of this being something that you can do. I was learning how to program and I was like, all right, so these people are like me, even though obviously a lot older, but it didn't seem like this mystical, out of reach thing. So even when I was younger, I was like this; it just seemed natural. That's what I would end up doing. And that's forward later on when I went to college and studied computer science and I was around tons and tons of people at MIT; everything was about starting companies. Like, that was a big thing.

This was right around when the dot-com thing was brewing. So it was just this perfect storm where I couldn't imagine doing anything else. And even though I graduated, I got a job for the company called Sapient, which was one of the big systems integrators at the time. And then I worked for a consulting company called R2D Little, but in the back of my mind, it was only a matter of like, soon as I can, I'm going to go start something. Yeah. Great. What did you lean into in terms of career? Why?

Like what sort of startups did you start, because you've started 20 startups. What did you lean into? Is there a specific niche within tech that you went down? Yeah, that's a great question. So sort of starting out when the.com thing was first taking off, everyone was trying to come up with billion-dollar ideas. So we were trying to come up with the big ones and we kind of did brainstorm a lot of the big ones, but the problem is it was such a race to get to those online chats; we had that idea before IRC or IRQ and whatever came out.

So we had all these different ideas, but very quickly we got to the point where we realized we couldn't just be competing to try and get these hyper-competitive things on the market. So we said, Let's do the picks and shovels approach. So during the gold rush, there's a lot of money made by people like Levi Strauss and people who sold the picks and the shovels to the gold rush. we said, okay, let's go out there and help other companies get online.

Very quickly, it wasn't intentional, but we sold a bunch of websites to companies. And then at one point we sold State Street Bank, which was a huge financial institution, still a huge financial institution. The next week we sold Thompson Financial. So fast forward two years later; we're our financial services consulting company, right?

Once we sort of sold those two and started digging in and building apps for them, it didn't, at least in that particular business; that was it for the next few years Everything was financial services. So ultimately we sold the company. Yeah.

Cool. All right. Well, this is a good question. So why sell the company? God, the motivation is very situational. Right. So for that particular time, literally to the minute, it was the no-brainer decision. And what I mean by that is that we were talking to venture capitalists about raising money during the time this was in early 2000,.

So we were; we were a pretty good growth clip. And the next logical step was to raise funding, but we heard about this company that was interested in talking to us. That was kind of like us, but a lot bigger. I had a few talks with them and we had a meeting with them on March 10th of 2000, literally at 4 PM. I'm not making this up. Like in the meeting, the meeting started at 3.30.

At 4 PM, we had an offer made to us; at that very moment, the NASDAQ hit a tie. So it was kind of this weird kind of the moons lining up, right? So we weren't actually thinking of selling the company at the time, but we kind of got an offer. couldn't refuse. Now.

In hindsight, it was 10 times more of a no-brainer than it looked like. So it seemed like a really good offer. This is a great company. They're aligned with our values. Like everything, everything looks like us only bigger. We'll actually get a lot more resources. In our case, it was actually, we jokingly called it a reverse acquisition because our client was pressuring us because we were about a 15-person company.

And the project that we were doing for Thompson was growing so fast that they needed a much better, bigger team. wanted us to add like 10, 20 people to it. Fast forward a month after the acquisition and snap our fingers.

We had a 30, 40-person team. So a lot of it was that we were able to acquire a ton of resources from the company that bought us to grow this project a lot faster than we would have been able to. But the other thing is what happened the rest of that year. I mean, that was when the whole.com explosion happened.

That was pretty much the minute to make a deal was the deal, you know, the time that we did. So we're very lucky that we got out of that because I think otherwise what would have happened is we probably would have gone and gotten a venture capital deal that year, which would have forced us to take on a bunch of debt and run like crazy. then you got a business when the whole bottom fell out.

Yeah. Get a bunch of debt, build a big team, have it break down and then freak out. Right. And then freak out. Yeah. And so literally, what was weird because we were running a 34 % profit margin? We were pretty proud of what we had built as a business. Yeah. And the VCs were like, What is a profit? Like profit was not one of the words that they were used to talking about in these meetings. It was a very bizarre time.

And what we need to prove to them is that if we give you $8 million, prove to us that you can lose $10. I mean, literally, that was the mentality. It's like you have to prove to us how you're going to run this race and take over the world before anyone else gets there. And that didn't feel right to us.

And in hindsight, it would have been 10 times the catastrophe that our instinct told us it would have been. Such an interesting mindset, right? To say you're making X amount of money. How can you spend more to get growth when it's not about just spending money to get growth? It's accurately spending money in the right places and being profitable that can allow you to stay in the game. Right? Exactly. Except when there's so much noise, nobody can react that way.

And even in that deal that we made when they acquired our company, mean, the exact language he used as we were going through, as he said, that our stock price just closed at 50 times revenue. So we can pay you five times revenue. So, first of all, from our perspective, we're like, well, five times revenue works out just fine for us. We're perfectly happy with that, but we were sort of scratching our heads, saying the idea here is that our revenue immediately gets multiplied by 10 in terms of valuation from their perspective, right? Right.

Because of the stock price. Now, again, that's not how the world worked out because of the whole.com crash, but that was the kind of logic that people were using to drive deals. And it's hard to, it's hard to say no to something like that. Especially on the sales side, what you'd be stupid to, right?

So what are some of the other things that, like you'd learned through the acquisition, somebody that's looking to sell their business, it'd be valuable insights to know. That the March 10th of 2000 at 4 p.m. was just the beginning of the process would be the first thing I would say. Yeah. Right. So we walked out as if that weree a Friday afternoon. mean, we obviously were stunned and ecstatic and I went home.

I went to an Acura dealership that had my dream car NSX sitting right there with ropes around it. And I was like, I'm going to buy that car. I did buy that car eventually, a few months later. So it was all like, that was sort of what our mind was. But really what was happening was that that was the beginning of a four-car. This hellish process. Where the deal collapsed twice during that time period, there was so much emotion—there's so much just craziness that kept trying to kill the deal. four months, that's pretty fast as well. Right? Like you can take a lot longer than that as well through DD.

It could certainly take longer than that. Yeah, that particular four months considering all the pressure that was going on and there's so many different things happening that four months felt like an eternity. And obviously we had some of our people say, I'm to go take a job somewhere else. like, no, you're not. You can't do like, you had to keep the thing intact during that period.

were you having to renegotiate contracts with employees and stuff like that throughout that period as well to keep them on for the acquisition? I would say absolutely. I wouldn't use the term renegotiate. We definitely change people's salaries quite a bit.

Yeah. Yeah. Yeah. Okay. And so just, just for people listening, why is it hellish? What are some of the things that make it so hellish? Because I think what happens is if I go back six months before we sold the company, standing in line of a bank, if we had made a mistake, kind of, we weren't as aggressive with our accounts receivables we needed to be. And so we burned our credit line of a hundred thousand dollars. And I was in line at a bank in America with a stack of credit cards.

where they each had a sticky note of how much I could take out to cover payroll. So that was like liquidating like $60,000 on credit cards, which was basically going to buy us two weeks of payroll. So yes, we did get the check from the client for that blew up, but to go from that kind of stress to suddenly getting that offer and starting to picture what it was a life-changing offer, right? So I was trying to picture what it was going to be like, but now you're still in this limbo zone where you're not there yet.

And now the lawyers are creating tons and tons of questions and issues and all sorts of weird things that need to be resolved. And meanwhile, you're trying to run full steam ahead and you can't tell anyone in your company that you have this deal. It's a lot of craziness going on.

So it's just you presenting information and data for DD; nobody else? There were three of us. So there are three of us founders who were constantly just collecting all the due diligence information and negotiating it. And actually, in some cases, we had to come up with creative solutions to save the deal at certain points because some people get really focused on whatever their thing is. So for instance, we had had a settle the illegal dispute might maybe nine months prior to lock solid settlement, but the acquirer was like, well, what if this person comes back and says, That's not a good sell?

Like there were all these different, what if, what if, what if, and then you'd think the next sentence would be, Why don't we do this to mitigate that? But no, it's like, What if he comes back? And so it's just, sort of, just become this thing and they're like, well, I don't know, this deal is going to fall apart. And finally, we came up with the idea of why don't you throw a quarter of the deal in escrow so that if that person came back and whatever, everything blew up 10 times worse and possible, you'd still be covered. And like, okay.

And I think what was weird is we came up with this creative solution. It was pretty easy. How come no one else had come up with that? How come none of the advisors would come up with it? Yeah. So you basically put, you left a quarter million of the deal in escrow and a quarter of 20, 25 % of the deal. Yeah. 25 % of the deal in escrow and didn't take out a certain period of time, which is three years. Yeah. Three years. Right. Three years.

Sella noted that no advisor had advised on. Did you have any advisors on their side? Like, did you have acquisition advisors on their side or on your side? We had our legal team, which, to be fair, gave us great advice. That was an example of something where the emotions had imploded.

I think it might be someone on their CFOs team at the acquiring company who had come up with that concern without coming up with a here's a way to mitigate that resolution. Yeah. Right. So it sort of came up; they just saw it as like, my God, it's damaged goods as opposed to this being a math thing. Right. It's like, if this is in the worst-case scenario, multiply it by four and you're more than covered by that escrow mode.

But it's like, are those the kinds of things that you have to come up with sometimes to shepherd the deal across the line? We did get a voicemail at one point from our law firm, from a senior partner at the law firm, advising us to walk away from the deal. And we're like, nope, no way. It's not going to happen. did they advise this? They were just because of all the things going back and forth. And we were looking at it like, You don't see the picture that we see in the market, what we're trying to accomplish, how we're working with our client.

I can see from the outside looking in and having a different perspective. I want to explain this for the audience: when you are acquiring or selling a business, typically what you do is try and make the business as least risky as possible for somebody who's going to acquire it. Now in your situation, Jeff, you have an offer, you have a meeting, you're not expecting an offer within 30 minutes and then you're selling the business.

So you had those four months that you had to try and decrease this eight-figure acquisition exit within a four-month time period. of course that was absolutely hellish, right? Like it's, like multiple powder kegs. Yeah. They throw in all these risks. You like, what about that credit card debt? What about that? It's five or 10, the stack of credit card debt that you had. What about there's a lawsuit?

What if they come back and then there's probably what a bunch more of those that you had to sort of combat, right? Yeah. And actually the funny thing is it becomes an ego thing too, because the law firm that was representing us had been the one that had settled that lawsuit.

So they probably took it a little personally—what do you mean this thing's iron? This thing's locked down tight. So that's where it gets a little bizarre, right? Yeah, absolutely. So was this your first act on the sale? Your first exit? That was, that was our first sale. Yeah. And it was unplanned.

So with these other 20 startups that you've started with the second one, did you plan the exit at all? I'm from the blank whiteboard, which is pretty uncanny. Literally the blank wall we were designing. is a destination weddings.com. And literally, when we were starting, we said, Where is our position going to be in the marketplace? And how is that going to make it so that we become strategically critical to some other player in the ecosystem? So I don't know if we use the word toll booth. That was kind of a mental model. Like we're going to become a critical part of the ecosystem that someone's going to look at this and say, okay, we need to have more control over that piece because they'll just notice us over time. So that was literally one of the first conversations we ever had starting the company.

Yeah, I love that. How do you position and create a business that the larger fish in that pond has to eat it? Exactly. And the way to think about it, right? So you've got your, you know, a lot of people think of, okay, what's our product? And they think of product market fit.

And so there's for us in that business, the obvious product market fit was creating the best possible wedding experience for couples having destination weddings for their guests. But there was another product we were creating the whole time.

Right, which is, what is the fit for someone else who might want to add this strategically to their portfolio? And so did you have a timeframe that you wanted to sell it or were you just like, Let's just build it? yeah. So that was obviously part of the founding thinking about the exit, but more of the founding was thinking about, like, how do we take over the space? mean, I think that there's something fun about a blank sheet of paper, right?

Because you can dream big. so, especially in that case where you had this massive industry. literally like, even at that time, I think it was 16 % of all weddings were destination weddings. And there was no super brand in the space. It was the most fragmented industry possible. So our thinking was, well, geez, if we just get in there, we bought the domain name for $10,000, which was kind of hilarious. It totally changed my image of domain name squatters. used to think of them as like the most wretched human beings on earth, right? They're just in the way.

And then I realized that if that domain hadn't cost $10,000, some other small competitor would have picked it up years before we even got close to it. became this barrier that was like, if you're not serious enough to go after this market, $10,000 is the entry price. Now in hindsight, that was the best deal—the best $10,000 I ever spent.

So that was sort of our whole strategy: define what the super brand would look like by the domain name to basically declare ourselves as a category leader from day one and then work like crazy to fill that brand over time. And you can even add the offsets and subsets of that domain name as well for the business you are purchasing and just like owning that sort of domain in like.io.com.co.uk, like all of those different as well. I will tell you because I didn't know how important a domain name was until buying that particular one.

It created a massive tailwind for us. It really helped us build our brand because people would be more likely to assume that we were the category leader because of the domain name. So it definitely did not hurt. So good for branding. And so what did you learn through the sale? So once you had a buyer, what did you learn from this sale, this exit versus the first one? This was, and this was a crazy one too. So I think this is going to be a weird place to go down, but I would say that there are strange technical considerations that can take a deal.

And what I mean by that is so like it's February. I think 2011 at the beginning of the month, we had put together the documents for the sale and it had like, February 28th at 5 PM was the deadline, but that was so far in the future; that was like a million years in the future, right? We're like, that's not going to be a problem. So you can see where this story starts to go, right? Like that's so far in the future. It's no big deal. Right? So we'll have this wrapped up by the 15th, right? Which we didn't then, but no big deal. It's just a few more things and we'll get some signatures. We'll have it wrapped up by the 22nd. Okay. Not quite right.

And then Friday, the 25th was, we were going to close Friday, the 25th little close for comfort, but no big deal. Right. The secretary of state of Delaware, the Delaware secretary of state office, makes a mistake somewhere. Somehow they type something wrong and then we can't close. now we just blew that Friday and we're going into a weekend. that Monday is February 28th. So now suddenly it's like, and meanwhile, egos are getting hot.

So, just to put where that deadline was, my instinct was that if we had hit that deadline, it would have forced us to read and would have set us back a bunch of weeks, which could have been enough to blow the deal up. if you go to that Monday, the 28th, it's like, okay, this is what's going to happen now, right? It's in the universe's hands as far as I was concerned. Yeah, true. All day, I'm just sitting there, like, What's going to happen? And, at 3:52 PM, the deal went through.

Okay. So one hour and eight minutes, if some mistake had happened on that day, I think that the deal could have blown up because to do new paperwork would have just been a huge hassle, tensions were getting tight. So, so what do you mean? Like the deal went through. you mean that they put money in escrow or no, no, no, like literally it had to get signed by there was something about the deal that had to get signed by the 28th and we had like 43 investors because of the way we had done our investment round. So when you start that, you bring in a bunch of different investors and when we give an investment round, we bring in, yeah, brought in, was like 28 individual investors. This is a pre-document sign. Okay.

One of the signatures came from, like one of our investors was on a yacht sailing around the world and had to wait until port to get to a fax machine at like a Kinko's or whatever they had and whatever country he was stopping at to fax; that's what wrangling signatures meant in that process. So the 2010, 2011. Right. Yeah.

Which I know someone's going to say, okay, DocuSign was available. okay, in hindsight, if it was then oops. mean, it has just started, but who knows? mean, 2010, it's still very early days with internet still like 10, only like a decade-ish old. Yeah. Like in the public anyway, I mean, people were using it before that, but not many people knew about it. But it does show that, like, this was literally a technicality that could have blown up the entire thing because the extra people were so, and it's again, it's not because of anyone's personality.

There's so much on the line when you have one of these deals going on that the temperature just rises. So if we had missed that deadline and been forced to redo everything and get all the signatures again and wrangle everyone, all these people who are like, yeah, they went along with it, but maybe next time now we have to go and take another 43. It may have just not; it's not likely it would have gotten through the next round.

This is the thing that I explained to anybody that's a try and achieve anything is that when you put a deadline on something, you actually have this time period that you need to achieve something by. So of course the pressure is just going to build and build and build until you get to that deadline.

But if you didn't have that timeframe, if you didn't have that date and it went an extra couple of weeks, it would have been totally fine. Right. But I'm sure there was something on their side or your investors side that we liked; we need to have this by this date. I'm sure there's a bunch of parties involved that needed to settle at a certain time.

So congrats on the exit for that one. Now, so from these experiences, like from your 20 startups, are you doing any now, or are you mostly just consulting? Because there's a bunch of things that you do and services that you are helping entrepreneurs with in terms of, like breakthrough blockages and helping them dominate their space. What do you spend most of your time doing now?

Yeah. So it's a combination of two things. I'm coaching founders and like rising new startups in terms of helping them get going. And then I think the other place where I'm most excited right now to focus my time is on generative AI. And I'm not the only person on earth who's looking at that, but there's so many parallels to 1994 in terms of, when I think of what the web was like in 1994, and you just saw this amazing potential that was going to come to fruition and took time. It took some ups and downs to get there, but you could just tell this thing was going to change everything.

I've been looking at generative AI over the last year or two, and I've spent a lot of time experimenting and playing around with all sorts of different aspects of it. And I just see it's something that's going to have a huge impact on everything. a lot of what I've been doing in the last six months is just playing, experimenting with that and seeing what kind of workflows we can do.

That's all brought me back to the financial services sector too. So we're actually working on compliance, using it for compliance-related issues. Cool. Yeah. I mean, there's so much value in generative AI.

that to get to the next stage of AGI and all that sort of stuff is, I think there's a lot of speculation around timeframes for that. But I wanted to dig into some of the things that you're doing with helping entrepreneurs, like breakthroughs. What are some of the most common blockages entrepreneurs that you're working with actually have that you find to help them? What are some of the things you do to help them get? Is there like two or three common blockages that they go through and some of the things that you do to help them move past those?

Yeah. So I think one of the most common things that I see, and this is across tons and tons and tons of founders I've talked to over the years, is I call it the stuck on the launchpad problem. And it's sort of like someone has this; this idea comes to them and they get all excited.

Here's my idea. And then I'll talk to them six months later and they get the same pitch. And I talked to them six months later, I keep getting the same pitch, but there's no progress because they kind of get lost in, like, what do I need to do to actually move this forward? And now there's a lot of frameworks that have helped in terms of, like, lean startup or minimum viable product, like that sort of thinking, but that's not always enough for people to actually make a meaningful step forward because I think it's hard for them to take the science of it, the scientific extreme, but make sure you meet with a hundred customers before you do anything and research every little thing before you try anything.

Right. And then the other extreme, which a lot of people do, let's just start building and hope for the best. And neither of those really seems to work out. There's sort of like, what I try to do is help them find the instinct of, like, what do I really need to do to make big progress? And instead of thinking of MVP, I try to think of pulling a rabbit out of a hat. Like when you show your demo to someone, because I know they say, Okay, if you're not embarrassed by it, you ship too late. Right. But that's, it's not that simple. It's you have to do something magical in that demo.

You have to pull a rabbit out of a hat and it can be an ugly rabbit. can be dirty. can be covered in no nastiness, but if you pull a rabbit out of a hat, the person you demoed to, they're going to take a second meeting. Yeah. Right. you did something interesting. Yeah. It's got a bit of magic on the side. Right. Exactly. And what informs, because going back to, okay, what are the problems that people have, is that I think that for it to be a rabbit, it has to do something meaningful to something that matters. so I think a lot of founders find a problem and they start solving it without asking, Is this really an important problem?

Right. Is this a super high consequence problem to solve? And so you have to really churn through and say, Okay, is this the most critical problem to be solving? then before you think of, like, what's the product, you have to think of what promise would be interesting. So if you're validating, if I could do this, would that be interesting? Right? Yeah. Yeah. If you could help that person in that space with that type of problem that's important right now, is it going to be interesting enough? Right? Exactly. They have to be able to visualize that.

Because then, you know, you're in the ballpark, and then, okay, now can I build a product to meet that progress? So imagine if I was like, I was at the drag strip and the NSX that I had at the drag strip was kind of in the middle of the pack. the zero to 60 time was like four and a half seconds. know, not the best, not the worst. If someone came to me and said, I can get you a car that can do zero to 62.2 seconds. I'd been okay. You've got my attention. Yeah.

Now the next so okay, so that's a promise that has my attention. Now the question is, can you deliver that promise? And that's where the dance comes in. So the rabbit you pull out of a hat has to attack like a meaningful problem. has to have a promise that's going to get them excited. And it has to have some credibility of being able to deliver that promise. Right, right.

And so what about people that already are in business? They're making a profit, and they have maybe one or two blockages; what would those be and how do we help with those? Like they're not pitching, they're not starting up there. They're in business. No, it's a great question. It's funny. Like, I'm kind of obsessed with the idea of product-market fit. And I feel like a lot of startup founders and business owners in general think of it as like the stage that you went through a long to like startups look at as a future stage that you're desperately trying to get to. And then ongoing businesses.

Think of it as something in the rear view mirror. Like we checked that box three years ago. And it's like, yes, you did, but the markets are changing so fast. The expectations are changing so fast. And people are like, and I talked to people like they're trying to minimize our churn.

It's like, okay, that's fine. If you really understand where your product market fit,fits you're in product market fit, then yes, minimizing churn is a good thing. If you're not in product market fit, there's certain people you want to churn. Yeah.

Exactly. And you can't know what product market fit is if you aren't speaking to your customers and clients. Like this is what I like to say to back up your answer. love where it's going is that the starters and the founders don't grow the business. They started, but the customers grow it.

And what you need to do is listen to them to give them what they want at different stages of their journey to either decrease churn or provide them what they're actually after to retain them. And your product will change as the environment changes. Sometimes there's more money in the market. Sometimes there's less money in the market.

Sometimes people need these certain features or not, right? Based on the environment. So you need to have that hat or that mindset of evolving your product based on what your customers and clients want. Obviously that you don't want to go too far and just make a Frankenstein product where it just suits everyone. That's just not right. No, you're not a star. I believe the clients build the business up to the start. Absolutely.

And I can tell you a crazy story about, like with destinationweddings.com, where I learned that sometimes the PMF tuning can literally be around positioning and not even product. And what I mean by that is like we were doing all sorts of split testing on a website.

This was long before there were any tools to do split testing. So we had to build our own Frankenstein split testing tool into the site, but we did. And we were running it to the point where we had had six split tests in a row that were dead heats.

And so what that means is that we weren't testing variables that were important, right? Which is fine. So we were, we had ideas, we tested the ideas and we got nothing out of it, but we were like, okay, keep trying, keep trying. And at one point, my wife had the idea. She's like, What about the stress angle? And we talked it through and we came up with the idea of stress free and it was like, okay, so let's test that.

And keep in mind, this was already a pretty well optimized website. I would have thought, like the businesses you're asking about, we're doing business. Like we have tons of clients. Like things are moving great, right? But let's try what is stress-free due to it. And we changed one change in our headline where there was the control headline was what we had pretty well optimized was like finally the way to something travel don't remember it all, but the new headline was finally the stress-free everything else the same and 43 % uptick in conversions from that one test. Congrats.

That's all exploded. mean that literally that learning, we realized that, okay, we've been talking around this. When we say stress-free, it hits our ICP dead on, right? They're like, Yes, finally, these are the people I want to talk to. We took that and we redid all our marketing. I mean, that probably was worth a 10 X increase in conversion over time in terms of like changing everything around it. That's probably what got us on the 500, those two words. And what's interesting is that was a positioning change.

I would say our PMF was better after than before more because it changed, honed our positioning more than like changing, like, okay, what our actual offering is. Also, when you use the languages and the copy and the words that people want to hear when they purchase the product, I'm not saying that it doesn't provide, but it does or doesn't provide it. I believe it has some level of placebo effect that product provides what they've purchased because they believe anyway. Right.

And I'm sure it does, but you want to do this in an ethical way, but it helps people have a better journey through using your product and service when you hit the nail on the head by resonating with them with the right copy. Right. Well, so here's here. It also does too. It created and for us, you're ready for our business and identity, right? Okay.

We are the stress-free provider that became an identity, which kind of created feedback loops that made the product overemphasize that. Funny story would be like, we had a couple that was, they showed up in Mexico for a wedding and they went to the hotel to check in and like, we don't have you here. Right. And then they said, Yeah, we're with destination weddings.com.

And it was like, no, total mix-up. No, not a big deal. We got you. And so these are the sort of things that created the pressure that we knew that anything that could damage our brand—anything that went against the stress-free thing would damage our brand.

And so I could see how this kind of wrangled the supply chain to make sure, like, if you're going to do business with us, you're not going to do stuff like this. Yeah. You're not going to make it difficult for our customers. You're going to lose a bunch of clients or us booking wherever they're staying because you're too stressful of a provider to work with us. Yeah. I like that.

And so to bring this full circle, I would say, so any business, and what's what I love now is there's scientific approaches to measuring your product's market fit until you engineer yourself towards it. If you Google superhuman.

PMF. It's one of the greatest articles that's ever been written on the topic by the founder of Superhuman It did use the framework by Sean Ellis, who was the growth, one of the early people at Dropbox. He coined the phrase growth hacker. came up with a framework for measuring and engineering towards PMF and then Superhuman used it and had an incredible outcome from it and wrote this entire case study on, like, here's how we used it.

Here's how it happened. He says the short of it is like, you're asking a survey, you're sending out a survey to your customers, and the first question you're asking them is, if we were to completely disappear, would you be very disappointed, somewhat disappointed or not disappointed? It's a very powerful question, right? So it's not net promoter score. It's like, Hey, do you like us or not like us? It's if we got wiped off the face of earth, would you care or would you really care? Would you not care?

And the people who say very disappointed, that becomes your PMF score. And once that's 40%, you're in PMF and everything goes your way. When that's not at 40%, life's a grind. Yeah. So the good news is, like, there's a framework. definitely recommend people check out that article. It gives a lot of good insights in terms of how you measure where you're at?

How do you keep going? But most importantly, don't just assume because you were in PMF three or four years ago that you're in PMF now. Yes, I totally agree with you. Wow. Jeff, thank you so much for your time. Where can people contact you?

Yeah. So, I mean, the easiest way to find me right now is on LinkedIn. If you just go to my profile on LinkedIn, feel free to reach out. I'm always happy to meet new founders. It's exciting to me to just learn that people have some of the craziest and coolest ideas. So if you've got one, definitely reach out.

Yep. Love it. Thank you so much, Jeff. I appreciate you and everybody that is listening.

Thank you so much. And I'll speak to you guys soon.

Awesome. All thanks, Jaryd.