“I’m a down-and-to-the-right guy” are words you almost never hear in tech. Especially not from a serial entrepreneur with two previous exits to his name. 

Dan Hanrahan told us that his most valuable day at a company is the first. After that his value goes down and to the right. 

While I am sure many of his employees might disagree, the point still stands that Dan is an expert at getting businesses up and running. 

We sat down with him and talked all about launching and scaling startups. 

Dan Hanrahan is a serial entrepreneur, having started 4 companies and sold two of them thus far. He was employee number one at Brooksource, and Indy-grown staffing and recruiting company.  the Co-Founder of Haulstr. An Indianapolis-based software-powered home services company. They offer mulch, patios, landscaping, and dumpster rentals. 

He was a previous partner at iGoDigital which sold to ExactTarget and the founder of Sigstr which was acquired by Terminus. 

Be sure to check out these great clips from the show:

  • [6:50] Starting a software company
  • [8:06] The failed time card venture
  • [9:30] Advice for non-technical founders
  • [16:47] Transitioning from Startups to Scale
  • [24:19] The silver tsunami and the opportunity to modernize small businesses
  • [33:58] Acquiring a business vs starting from scratch
  • [49:09] The concept of time and its importance

Get IN. is the show focused on the unfolding stories and most extraordinary innovations happening in the heartland today. Get IN. is brought to you by Powderkeg and Elevate Ventures.

In our conversation with Dan, you will learn about:

  • Advice for Non-Technical Founders: As a non-technical founder himself, Dan offered practical advice on working with technical co-founders. He emphasized the importance of treating your technical co-founder as a partner and the need for trust and communication in the relationship.
  • The Silver Tsunami: Dan discussed the concept of the “silver tsunami,” the impending transition of millions of small businesses owned by baby boomers. He sees an opportunity in acquiring these businesses and applying technology to modernize and grow them.
  • Empowering Entrepreneurial-Minded Individuals: Dan believes in hiring people who have a desire to start their own businesses and sees his company as a stepping stone for them to achieve that goal.

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Episode Transcript

Matt: From the crossroads of America in the Hoosier state of Indiana, this is Get In, the podcast focused on the unfolding stories and extraordinary innovations happening right now in the heartland. I’m Matt Hunckler, CEO at Powderkeg, and I’ll be one of your hosts for today’s conversation. I’m joined in studio by co-host Nate Spangle, Head of Community at Powderkeg, and on the show today is Dan Hanrahan, co-founder of Haulstr.

Dan: Just the scrappiness and the perseverance to do what has to be done today.

Matt: Dan Hanrahan is the co-founder of Haulstr and Indianapolis based home services company. He was a previous partner and iGoDigital, which sold to Exact Target and was then of course acquired by Salesforce. He’s also the founder of Sigster, which was acquired by Terminus and he has been doing some really interesting things in entrepreneurship via acquisition.

And we’re going to talk all about that today as well as Dan’s story. Dan, welcome to the show. Thanks for doing this.

Dan: Thanks for having me guys.

Matt: So excited to talk to you, man. It’s been a while since we’ve caught up and I know you’ve been busy. It is. But before we dive into the latest on what you’ve been doing with Haulstr and what you’ve been doing with entrepreneurship, just through acquisitions I’d love to just chat with you a little bit about your earliest kind of entry into entrepreneurship.

Sure. What were some of your earliest memories?

Dan: It’s a good question. It may be serendipitously. My first jobs happened to be with really small businesses. Oh, that’s great. My first, when I was 16.

Matt: What was your first gig?

Dan: Yeah. Was my first job I was 16 and I was building retaining walls, so I weighed like a buck 10 and I had retaining wall stones that were about 90 pounds.

Matt: Awesome.

Dan: And the two guys that ran the comp country the the company they were in, machines while I was, doing my best to build a wall. So yeah I, what, one just random story from there. I remember I didn’t know how to drive a stick at about a mile long driveway on Michigan road, which is a 50 mile an hour road.

And they left me with a truck and told me to get to the job later. I got in the truck. It didn’t have a stick. And so I figured out in that mile drive, how to quickly merge into oncoming rush hour traffic at 50 miles an hour. And I think that’s what entrepreneurship is like.

Matt: Yes, that is what entrepreneurship is like.

Dan: I didn’t stall

Matt: You’re prepared for the first job. Yeah, that’s awesome.

Dan: So I didn’t seek it out. It just But, it just came to me and I realized that, boy, I asked those guys a lot of questions and had a lot of respect for how hard they worked and the ownership that they had in their business.

Matt: What do you think was the number one skill or strategy that you learned in that first job?

Dan: Probably just grit. It was a hard job and those guys were smart guys, but they had, all they needed in life. You had good families and, nice enough homes and but at the end of the day, they worked their butt off and they had that autonomy. And I think. That’s what sort of stood out.

Nate: Were you always a founder? While you were working there? Were you still coming up with ideas? Did you have a high school hustle?

Dan: Like every kid in high school, I was always coming up with great ideas. Putting them into action, I don’t think I did a lot of that in high school, right?

I was running around playing sports and gosh, I worked in the pizza world and all those kind of classic high school jobs. I mowed some lawns and things like that but I didn’t really I didn’t really get that entrepreneurial itch until, maybe when I was 16, I had that job and then majored in entrepreneurship in college and…

Nate: What is it like to major in entrepreneurship?

Dan: At IU, the school was fairly new. It was entrepreneurial in itself. So I think it’s like super established and robust and Dr. K runs that program today. But when I went there it was just you made it up as you went and that really, was appealing to me. So I took my core business classes, accounting, marketing, finance, whatever else.

But then I had classes like, create a business and pitch it and we’ll have a fake venture contest.

Matt: Was Dr. Haberly teaching back then at the Entrepreneurship School?

Dan: He was.

Matt: Awesome.

Dan: They were good days. We had a lot of fun.

Matt: Yeah. Haberly’s the man. Just By the time I was at IU, I was in the Entrepreneurship Program as well Dr. K was there.

Dan: It was a real program by then. Yes.

Matt: But Haberly still had this skunk works thing that every summer that I was at IU, I would go to his house. I think it was for two or three weeks. You would go every day. And you’re just like sitting with five to 10 other entrepreneurial students in his basement.  And he’s I have, I’ve prepared these, fictional case studies.

Dan: And he just loved it.

Matt: We would just go through them. And then, like you’d get like almost to the end of the case study and he’d be like what actually happened was, in this fictitious case study, they were all like real scenarios that he had been that’s really cool.

You got that exposure.

Dan: Actually went and knocked on the door of the entrepreneurship program. It was probably 2000. Oh, gosh, 2012. So after I go, it’s sold to exact target. We bought a little piece of land down there and started building a log cabin and I needed just to unwind my mind and I wanted to get back to entrepreneurship.

So I knocked on the door there and said, what can I do? Cool. And they were like, who are you and why are you knocking on the door? And I was like, I just need a desk. I’ll do whatever you want. So any kid in the whole school that had an idea, I spent a half an hour with them, asked them to guide them to somebody real that could help.

Nate: No way.

Matt: What’s the number one piece of advice to student entrepreneurs? When they’re in that stage of Hey, I’m going to college, but I’ve got this entrepreneurial idea. Yeah. What were the things that you find yourself like repeatedly? Giving the same advice on

Dan: Great question, and I think there are two things that apply whether you’re a college kid or not. One is just start doing it. Yeah. Even if you don’t have the money or, the experience or whatever, you can take your idea in your head and put it to a piece of paper with bullet points. And then you can put that to a slide deck and then you can call a bunch of people and ask them to give you feedback about that.

So just start doing it. Every one of those steps that you take makes your business more real and helps you understand whether or not it’s actually worth pursuing. So just start doing it. Yep. And then there may be a leap of faith where you need to quit your job or quit school or, whatever it might be and, or raise some money.

The other one is, don’t go to the business club if you’re a business kid. Don’t go to the biology club if you’re a biology kid. Or the software club if you’re a computer science major, right? If you’re a business major, be the only business major at the computer science club. Because you need a wingman, wingwoman to cover your blind spots.

And you don’t need the group think and the kids that are taking the same classes or whatever. So whether you’re in college or not, that’s, I think, probably one of the biggest things.

Matt: What was the first real venture that you started?

Dan: So I out of college. I joined the smallest company I could find. My dad was a he started the mail room of an insurance company and was in large corporations. And, but my mentor in a lot of ways. So sure. When I was like, Hey, I’m not going to go work at John Hancock or enter some big, place that recruited at Kelly school of business. And I was going to go work with Ryan Hasbrook and Jeff Weiser and Ryan’s basement on North Waldo Avenue to build a IT recruiting staffing business.

Yeah. My dad just okay, that sounds good. Go do that. That’s great. So that’s great. So anyways I was in that business for about eight years as a first employee. It’s an incredible business now. And at the end of that journey, I’d watched companies like, Google thwart companies like 3M is the largest companies in the world and they’d only been around for a few years.

And so I was like, I’m going to start a software company. I’d been around a lot of smart software engineers. And staffing and placing them in jobs. Sure. And we had a simple problem to go solve, which was we were literally placing software engineers and network engineers at corporations and then asking them to take a physical time card with a carbon copy and have write down their hours and have their manager sign it and fax it to us.

Oh my gosh. So it’s I can revolutionize this. Yeah. It’s probably, there’s gotta be a better way. Probably the easiest problem to solve in the world. So the Brooksource guys said. Actually, even before that, I said, Hey, I’m gonna start a software company. I gotta go do that. Thanks for everything.

And they’re like let’s start one. We’ll help you. That’s great. And so I listed out a bunch of ideas on a sheet of paper, literally called, header on that paper is Bush Light Night. We got some bush light. That’s great. Yeah. I still have it. And we went through those ideas and I’m like, I’m an idiot if I can’t make the time card thing work.

So three months, 10, 000 later totally failed. I had made no progress. I hired a software engineer that was great, but treated him, again, talking about your wingman or your partner. I didn’t treat him like a partner. I treated him like an order taker. And I was like, hey, here’s this thing.

It’s super easy. I’ll be back in six weeks to see how you’re doing. Meanwhile, I’m paying that person hourly, giving that person no guidance. My requirements were garbage. And so I came back three months later. It was not his fault. He’s a great engineer. It was my fault. And I just came back and I said, I don’t care what the next idea is.

I just know that I need a great software person. And to treat as a partner, not as a, an order taker. And so having that sort of technical co founder the next thing just, it became I go digital and off we went.

Nate: Do you have good advice for non technical founders? Like practical advice for non technical founders working with CTOs, technical people?

Dan: Yes. I think the main thing is for me, I need that person to be not like a fractional person I want. I want somebody in the business pretty fast. Now, if I rewind the clock to Sigster when we built that, I had a pretty clean idea of what we wanted to do. Yeah, I had a friend who was a sort of BA project manager Brad Whistler down in Bloomington and had a lot of experience in startups. And so Brad had an engineer, a rails guy that could write some code and Brad could be my sort of project manager. So I knew him well enough, and he had such a great track record of success. I know, Matt, Brad well.

Yeah. That I did say, okay, I’m gonna spend three, it’s funny, three months and 10 grand to see if I can get to my MVP. Yep. And if I can get to my MVP, then I’ll, maybe I’ll raise money and then maybe I’ll, hire a real wingman, which became Sam Smith who now is a co-founder at Demandwell.

Yeah. And so that experience was the antithesis of what I just said. But by that point, we’d been through the iGo Digital years. But if I was a first time founder, I would definitely want that person that that guy or gal to be a partner in my business and an owner, frankly, so that when a customer thing happens that I can’t fix because I can’t write any code, I know that somebody else is going to be up at midnight or, after they put their kids to bed or whatever and fixing the problem.

Matt: One of the things I’ve found working with technical co founders or technical leaders is you have to have an enormous amount of trust in that person. Are there things that you did to help develop that trust? Because I’m assuming you know about as much coding as I do, which is you can maybe follow directions and make an app if you follow step by step and have lots of tries at it.

Maybe. So how did you develop that trust with Sam or any of your other technical leads as you develop different businesses?

Dan: Yeah, it’s a really good question. I think having them on the phone listening to customers, even if they’re in the background, just to hear it firsthand rather than, hey, these are my ideas.

It’s hey, here’s what I’m hearing from customers. Let’s bring this back to the product and figure out what we should do and then helping prioritize. So giving that person, even though. I tend to have a strong personality and come in with a perspective. We’ve already sat down and we’ve agreed that, hey, these are the most important things in this sprint.

Whether that’s a week, a month, a quarter, or whatever. And just empowering that person to say, hey, here’s the five things we said we were going to go do. Which one of these do you want me to remove? Or, Who else can help us get this longer list now done and then half the time when somebody asked that question, it’s listen, those things are paramount and it’s all a con, a concept of time and just, Hey, this is super important, but it’s not as important as those things. So let’s put it on the list for the next sprint.

Nate: I would say you’re an idea guy, right? Yes, but a lot of ideas.

Dan: Yes,

Nate: Yes. So like coming in there, I can just imagine you in one of those first like product meetings. It’s got to do this and it’s got to do this and it’s got to do this. And they’re like, all right, you get to pick one for the next month, right?

Dan: Yes, but I’m also very aware of that flaw or whatever, superpower. Superpower depending on when I was younger, I did not have a grasp of that. As an, as a, at this stage in my career, it’s man I, did I just freak you out? Yeah. Because listen, these, and I like to start things with, Hey, I’m not talking about now.

This is just like a future discussion, but what if we thought about this and, in progressing those conversations before it distracts somebody that is actually making progress on what we really need to do.

Matt: That’s, I really like how you put that because I think that’s a common Struggle that a lot of entrepreneurial people have, they’ve got a lot of ideas.

They see how big the thing can be. And that is a superpower, but if you don’t know the weakness on the other side of that superpower.

Dan: I think the key is, as we say this all the time, in order to get to that stuff, we’ve got to survive. And in order to survive, these are the things we’ve got to go do. And if we do those well, then we have an opportunity to make a bigger impact and get to some of these next level ideas.

So just the scrappiness and the perseverance to do what has to be done today in order to get to tomorrow.

Matt: How did that work at iGoDigital? Those early days?

Dan: This is a funny story. There’s this guy, and I will name him because I tell him this all the time. So Ryan Hughes Ryan Went on to have a nice career at ExactTarget and Salesforce and is still doing really cool stuff.

Great sales guy. We plucked him out of college and Agua Digital recommended things on retail websites. One of our retail websites was a costume site. And so we were recommending like hot pants with kids costumes. And we were like, the customers like, do not recommend any adult costumes with the kids costumes.

And we were like that’s what mom wants. That’s what the data says. But that’s not what the brand wanted, right? And so we, we hired Ryan and Ryan’s job was to manually go through the data and flag any hot pants as Like adult product and then build the business rule to go back on the so that it’s like a super scrappy thing That’s amazing.

It’s a Ryan’s career in tech started by searching for hot pants products

It’s just humble beginning you’re like, I don’t know the machine can’t do it So let’s find a person and and then we’ll figure out how to unmate the stuff later

Matt: Yeah, it’s The Wizard of Oz approach, right? You got to have the person behind the curtain, making sure that things are curated, making sure things work the way the customers work.

Dan: That’s probably not on Ryan’s resume, but he’ll laugh.

Matt: That’s a great example. That’s a great example.

Nate: So that was the next, after your, the time card.

Dan: Yeah. So it went time card thing. I have a history of naming companies poorly. So we started a company called Last Piece Software on my name tag. I did like a business conference.

People thought it said last place software. But anyways, last piece software. We we, it was just a ratings and review system. What on a retail website, right? This was 2008. What Amazon had trying to bring all that stuff to other websites, ratings and reviews was really easy.

To add as a widget, so we built that knowing we would get some data and then ultimately power recommendations, which was what my partner wanted to wanted to build. And so as we were going through that at last piece software I ran into Eric Tobias. I’d known him in the past and I was trying to sell him ratings and reviews for his batteries website.

I was like, ratings and reviews will change your batteries business. And he’s like, why are you building that? I told him and it turns out on the side he had Best Buy as a customer. And was selling them like a battery finder. So enter my device and tell me the battery I need to buy. But he wanted to automate all that and use data.

And we wanted to build a recommendation engine. And so we put those two companies together and that became iGoDigital. We ran that from 2008 to 2012, sold it to Exact Target. I stayed at Exact Target for nine months. They got acquired by Salesforce, went to Bloomington, built a log cabin, started Sigster, we ran that for five years from like 2014 to 2019.

And hired a CEO to run that because I’m not a scale guy. I’m a startup guy. It had about 60 employees and it was just beyond my comfort zone.

Nate: What about it was beyond your comfort zone?

Dan: I like starting things and finding the early traction and then being a part of that, but helping the team that should take that and scale that. While the next thing that I see that we should start and scale I can go work on that. What was cool at Sigster is there was a an ancillary product of the data of that business.

And I was able to take that data and try to build that into a second product before, before we were acquired. So that was a lot of fun and that, that allowed me to scratch that itch for a year without just running out the door.

Matt: Was there anything that you learned in your couple of months at a big software company like Salesforce?

That you took with you even if that was maybe just something you learned about yourself.

Dan: Yeah. I Say this every now that I’m a down and to the right guy. I Think everybody wants to be up into the right But if time is on the x axis and value is long along the y axis of a company Yeah, my most valuable day is day one of the business what is the first thing that we can actually build fast and get it in somebody’s hands that adds value?

I love that process, the iterations involved in it and just going fast. So my current company at Haulstr we were able to do that. And I was, I, so I stepped back and I said, Hey, I know I’m a startup guy. I can help other people become owners. I’m fascinated by that, become an owner.

And helping people that have never been an entrepreneur own their own thing and what they’re uncomfortable with on day one, I love, and then what I get comfort uncomfortable with as the business grows, then they’re more equipped and able to step in and run the thing. Starting companies we have a bit of a, almost like a venture studio.

Yeah. It’s weird. I never thought that Haulstr would be that, but literally mulch mulch fundraisers is what Haulstr started as. Yeah. So taking tech and applying it to super non-tech businesses. Mulch, if Kristian Anderson, another high alpha guy said this really well, he’s Hey, I can’t be the best digital marketer in the world.

He’s but I can maybe be the best digital marketer, venture capitalists. And he started to segment the world. So I can’t be the best SAS guy in the world, but I think I can be the best like mulch tech guy in Indianapolis. Yeah. Yeah. There you go. Mulch tech. Like we’ll start a new company.

So that mulch business took off and then I’m able to get into the next one and we acquired a little patio company and plug that into the sort of e commerce customer acquisition model, the back office stuff that we had built with Haulstr and then we’re able to go out and bolt in a dumpster company.

So that’s a lot of fun because the framework of what those businesses need to run is there. But it needs a great operator. This is the equivalent of a technical co-founder is somebody that can run the logistics of a dumpster business. Yeah. While we help on the business side, drum up customers and pay taxes and things like that.

Yep. So that’s where it’s evolved. And again, it’s just getting comfortable when I was at ExactTarget, knowing that, hey, this is an amazing company. In such a pillar of the Indianapolis community, but it’s too big for me. Yep. And they actually gave me a Salesforce sort of person because I hated the process.

I was like, listen, I can go sell this all day long, but I don’t know all the boxes you want me to check to get this thing to Salesforce? And I was like, so do you want me to sell or do you want me to try to figure that out, be in the CRM and just go sell? Yeah. There you go. And so you had your wing person there too and she was I’m so good at process and I understand the importance of why that had to happen in a bigger company. But I, I wasn’t patient or mature enough to slow down and do that work on my own.

Matt: One thing I’m noticing as you talk about Haulstr and the business you have today, none of the companies I would categorize as software companies.

Dan: No not at all. I, so I, after Sigstr was acquired by Terminus. I wrote down, to Nate’s point, I have a lot of ideas. But I wrote down a few things that were important to me. And I whittled that list down so I could evaluate all the things I could go do. And the things that ended up on that list were three.

It was, I want it to be local, not that it has to stay local. But it has to be run locally in brook source. They could start or 8 11. They could start a staffing arm in Cleveland But I couldn’t do it from Indianapolis because it’s so relationship based so I want it to be local But if it wanted to take whatever we built and run it in another city great.

I wanted to be profitable Just so that the business could do what was natural for the business and then we thought if not that it can’t ever be funded But if we find that inflection point where we can pour gas on it, yeah, and then great we can go fund it and I wanted my family to understand what I actually did it like connects some dots with my family.

So my mom was always like, Hey, he’s in software. He could probably fix your computer. Yeah. Yeah.

Nate: No I love that. That’s such a good analogy for people in tech. I feel like I told my grandma I was in software and she, I thought that we still sold like disc like CD ROMs, disc of software.

Dan: I, we could, grandma, we could maybe we bring that back. Bring it back. Records are back. Let’s go back.

Matt: There you go. Records are back. Bring the floppy disc back. Bring the floppy disc. It’d be so cool. And like the actual floppy ones, like not the three and a half inch, but the like big ones that Oregon Trail we’re on.

We’re dating ourselves. Yes,

Matt: yes. Not me, Nate has no idea. Not Nate.

He has no idea. Although I did buy Nate a record player, so he’s a vinyl guy now.

Nate: I am a vinyl guy. I am a vinyl guy. I have two records. I have Chris Stapleton and I have Zach Brian, oh, actually three, and Elvis. And Elvis. Yes.

Dan: Eclectic. Absolutely.

Matt: He’s an eclectic guy.

Dan: Good work, Matt.

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Matt: I I would love to hear a little bit more about sort of the differences between software businesses and more brick and mortar, for lack of a better word businesses and also maybe some of the similarities.

Dan: Yeah, the beauty, and I’m so grateful for the time and sass and in Indianapolis, that, that journey and in the.

Fortunate timing to, to be launching Sigstr, right? When a lot of momentum was happening with High Alpha and some of the investment stuff here. But what the real value of that was, it was like a, an MBA on steroids because tech has been so analyzed, right? The the unit economics of a SAAS company and how you value SAAS companies and all these things.

So like that applies no matter what can you get, recurring customers, right? What’s the lifetime value? Like it doesn’t matter what you’re doing. And and so those lessons certainly apply outside of tech. And then there’s this other thing happening in the world. It’s a silly term that the SBA calls it the silver tsunami, like a small business administration.

And it’s basically, there’s, we all know there’s baby boomers. They own millions of businesses, right? There’s 10 trillion in value. In small businesses in the 30 million small businesses that are owned by baby boomers. And so if you break that down, all those businesses have to have a transition.

And there’s some incredible companies in there, and a lot of these companies have not been modernized. And so there’s this sort of trend of, oh, I’ll just go buy an unsexy business that has an applied tech, and then I’ll just apply tech, and then we’ll grow it, and then we’ll make it more valuable, and then we’ll sell it.

So at Haulstr in a lot of ways is the tech. There’s a lot of Sort of thing to drive e commerce and operations behind some of these small businesses that may need to transition. Some of them we’ve started. Some of them we’ve acquired. And we can plug them into that.

And there’s all these incredible opportunities out there. And when you start to look at those businesses, I start to think about the tech unit economics. Do you have recurring customers like are you building fences? If you’re building fences and you’re not doing repair work, you’re going to build it once for a customer and they may never need you again.

And so that revenue is less valuable than somebody that might be even painting houses every few years or mulch, which happens every year. So I started to break mulch down into a This was for a tech investor. My buddy was like, what are you doing? I was like I was like, it’s it’s a fascinating business.

And the economics are really good. And then an investor came up and started talking and she’s what do you do? And I, instead of telling her what we did, I started telling her the unit economics of this. Branch of mulch. So the ARR, like how much recurring revenue do you have time value, lifetime value, what’s your CAC, like all this kind of stuff.

And she’s she was just like, wow, and she’s what do you do? And I was like mulch Smile faded away But so to answer your question the parallels are there and being in software You just get a crash course in business in general.

Matt: You’re understanding where the business value is created And what makes an enterprise valuable over time.

And so you’re able to identify those things that are the hard things to manufacture out of nothing. And if you can go and find those quote unquote hard things that are hard to manufacture. From nothing. But then, apply the things that for you are easy because you’ve built them out at Haulstr.

You’ve done them, how to use software, how to use a CRM, how to use good digital marketing.

Dan: Yeah, and there were some other things too that I wanted to do, I’d never done direct to consumer. And so whether we’re doing firewood or mulch or patios or dumpsters or whatever the heck it is we’re doing, it’s primarily residential business.

And so when we started with mulch, I was like, okay, how, so we started with fundraisers. So we just went to churches and schools and the places where my kids were anyways and the teams that they played on. And we said, hey, we’re going to spoon feed you marketing content. If you share it on your social or in your email newsletter, if anybody clicks that link and buys, we’ll pay you as part of your fundraiser.

And so like those little things of like, how do we go to market and some of the things I never got the opportunity to do. There’s not, I’ve never run a sort of crowdfunded thing and like the Kickstarter campaign. So I’ve got an idea that I’m dying to go and do that with. So there’s just product led growth.

Yeah, is another one. There’s a few itches that I’ve always wanted to scratch see those Haulstr.

Matt: . I see signs all over the place, man. That’s like product led growth.

Dan: Poster led growth? I remember being at a conference, it was a Martech conference, and I was sitting there, and they, I was on the panel or whatever, and they were like, what do you see as the next big thing in marketing?

And I was like… Direct mail. Direct mail. And they just made fun of me. I explained why. You’re not wrong. We forget we’re emailing, we’re calling, and we’re buying ads on Google and we’re doing SEO. But some of the old school things are just, still work. So whether it’s a yard sign or a direct mail thing, whatever it is.

It’s still fun to

Nate: What are so I mean you’re Matt called them brick and mortar businesses. I like the term blue collar blue. These are blue collar Businesses what are let’s say there’s someone out there That wants to dip their toe into entrepreneurship. Yeah, what are two or three blue collar businesses that get you excited?

Dan: Yeah, that’s a great question So we I told you I’m terrible at scale and some of my initial founders are similar and so we hired an adult And Carrie’s a partner of the business now Carrie came from tech here in Indianapolis and he was thinking about acquiring a non tech business and so somebody connected him with me and then it was a long recruiting process to say, Carrie, why don’t you come over here and we’ll do this a bunch of times.

And so Carrie now is our C.O. Partner in the business. Super important piece of the business. But he’s helping right now. There’s a maintenance business and this is silly, but we talked about the power of signage and being in small areas. The beachhead approach, right? And so what is in a neighborhood every day?

It’s a thing that we all started like half the people on the podcast try said there was a first entrepreneurial thing mowing So we’ve got this 20 year old guy he’s amazing, he’s grinding it, he’s been in business three years, like small business, but he’s got a couple crews, but he doesn’t want to deal with the taxes and do all these other things and wondering how to grow and feeling on an island and so it’s so what we have is a bunch of businesses under the holding company.

It looks like one brand to the customer, but we’re really interested in mowing and bringing that business on board because his trucks will say Haulstr and they’ll be in the neighborhoods every day. So if something else happens, we can, cross sell right into that home. So mowing is super unsexy and super blue collar and anybody with a power washer or mower could start their own company.

But other things like irrigation or sprinkler systems. Just connecting those dots. A homeowner. This is the main thing. If I’m a homeowner right now, it’s really hard to get somebody to call me back. It’s really hard for the local service provider to compete with the national brand.

And so I’m also very interested in solving that problem. We’ve got a sort of a tech business weirdly starting up to help homeowners find locally owned, highly rated, super trusted companies that will actually respond to them. And so those problems, like if I’m a homeowner, it’s my biggest asset, probably.

Absolutely. And I don’t know what the heck to do with it nine times out of 10. And so I’ve got to rely on, maybe 40 companies throughout the year. How the heck do I find them all and trust them in a way that is actually helpful and not just like a lending tree approach where I put my project in and I get 15 calls back from anybody that’s willing to pay

Nate: Who knew that Indianapolis was going to be the home services capital, right? It’s like a v2 of that.

Dan:Yes. Yes, it is. Obviously Angie’s list. I have a ton of respect for that business as a homeowner I think there are other ways to approach that challenge that helped not only a homeowner but also the service provider in

Nate: The local approach that you’re taking to it right where it’s like a local hyper local like Indianapolis That’s where you’re starting.

Dan: In helping locally owned businesses and entrepreneurs Yeah, right compete with the national brand Because at the end of the day, I want the person coming to my house that, I’m one call away from the owner, that owner probably is going to be at my kid’s game or at my kid’s school or whatever that person that one might care a heck of a lot more than somebody that’s just collecting a paycheck from a national business.

That’s been, part of a rollup,

Matt: You mentioned a lot of the kind of more tangible things like unit economics that you look for in a business when you’re acquiring it. What are some of those intangible things that you personally value or you as a business value?

Dan: Sure. Community driven. Yeah. Trusted, been around a long time, right? And done things the right way. If I look at Eight Eleven, that was just such a lucky place to land. She felt they’re approaching a billion dollars in revenue. Yeah. And staffing is a business that is nearly impossible to differentiate. The only way you can differentiate is hire really well and teach those people not to cut corners.

And when you screw up, show up in person, apologize and tell them you’re gonna go make it right. And so if you do that for 20 years, you can have a billion dollar business, but most people aren’t that patient. And so I’m not looking for billion dollar businesses. I’m looking for companies that, that, that might be, a couple of hundred thousand.

And profitability not top line, but profitability and, but have built that over. And built that over 15, 20 years and have customers that trust them and come back year and year again. So yeah, some of those intangibles and community driven, just local as I’ve gotten older, my world has shrunk and I’m super interested in making an impact in my neighborhood first.

And my, northeast side of Indianapolis next and then expanding out of there and then building things and tools that if somebody wants to take it and run it in Cincinnati or wherever the heck you’re from, that’s awesome. I cannot compete from Indianapolis. And I think those businesses are fascinating because they’re not going to be cannibalized by Amazon.

And the minute I say that, there, there may be some weird ways. Amazon will have drones cutting you on. Relationships matter and having somebody in your community running the thing with a platform that makes it differentiated. I think that’s where I’m fired up.

Matt: When you talk to entrepreneurs or people who want to be entrepreneurs, and they’re like, hey I think I want to start a business.

What’s your take on starting something from scratch versus acquiring something new?

Dan: It’s a good question. I think it, I don’t think it’s a function of age. It’s a function of experience. And maybe a bit of both, right? When I’m 20, 20, I have, I probably, I don’t have kids. I don’t have a home. I don’t have a mortgage.

I have so little to risk and I can eat potatoes all day if I need to. I’m Irish. Yeah, there you go. You’re potato fueled. Yeah, so there’s less to risk. So why not start something and learn? And if it fails, who cares as I have more responsibilities and also more experience than I, than maybe acquiring a business that already has cashflow and a proven model.

Makes more sense because I can not only, and I don’t need a lot of cash to do that. I think this is one of the…

Matt: How much cash do you need to buy a business that in your mind is like worth acquiring? Maybe isn’t going to turn you into a billionaire.

Dan: Of course. But it… The business I’m looking at are pretty small.

So let’s say it’s a business doing a couple hundred thousand in profits. Typically something like that might be two to three X profits, right? It’s not SAAS. It’s not top line revenue multiples. It’s two to three X on the cashflow. So if you think about that, if I acquire it and I don’t even grow it.

In two to three years, I have the, I’ve paid for it. Now I own this thing that’s generating 200, 000 in cash every year. And so that is more like an annuity unless it’s a less risky acquisition in a lot of ways. And you can literally come to the table with no cash. You can do like a third SBA loan, a third seller financing, meaning the person selling the business will get paid back over the lifetime out of the cash flow of the business.

And then either a third cash out of your own pocket, or equity investors, or lots of other things. So you can buy a couple hundred thousand dollars in cash flow every year with no more than, 50 grand. And there’s a lot of ways to go find 50, 000.

Matt: Absolutely. That’s great. That’s just helpful. I think for people who are listening and maybe have thought Hey, I want to own a business someday, but I feel like I missed my window.

Maybe I have kids now. Maybe I’ve got a mortgage.

Dan: There’s one other thing too, and that’s just no matter where you go to work, try to find a path to ownership and find companies that are willing to do that. I think ownership is the ultimate path to whatever freedom means to you. And self I don’t know, I don’t want to say self worth but just believing that you’re working in something and you’re not going to, at the end of the day, I can’t, how many times have we all done this where it’s man, I did such a great job.

And then the company got all the benefits for it. At the end of the day, if you’re a partner in the business, if you’re an owner in the business and there’s a good outcome. You’re part of it. If there’s a bad outcome, you’re like I gave it hell. I was at a seat at the table. We did our best and it didn’t work out.

So just to me, I think asking for ownership, even as a very young employee or an ownership can take a lot of forms, whether that’s profit sharing or otherwise in the business, but finding companies that are willing to to offer that up. Is another way to have skin in the game.

Nate: Do you think that mindset is what made you unemployable?

We got to talk about that a little bit before.

Dan: Yeah. Nate asked me why I’ve been an entrepreneur and I told him because nobody would, should hire me. And I think, I’d be a fine employee if somebody said, here’s a problem, it’s really important to solve, go out and solve it. Come back and tell me what you learned in a month.

I’m really bad when it’s here’s a problem. Here’s how to solve it. And I’m, let’s talk every day about my path to solving it. And if there are projects. That can be run autonomously and things that just need to be solved and don’t have to rely on the entire team and the organization to be distracted from whatever the primary objective of the business is.

I enjoy those, but I’m not very good at coming into a larger business and filling a role. So

Nate: If you had advice to someone looking to get into startups, right? Maybe they want to be a sub 10 employee. Yep. What should they be looking for? What are signs that you could be joining a good team or signs you might be joining a bad team?

And if you could go back and give advice to yourself at what, 23, 22, coming out of college, what were you looking for?

Dan: The luckiest thing that happened again with Eight Eleven is they were a recruiting business. So all day I interviewed people and tried to match them. With the hiring manager at the end of the day, I’m not very good at anything, but I’m good at building teams and saying, okay shoot my product had on no matter if it’s a software business or something else, what is the next thing that needs to be done?

And if we don’t have a person that can do that, then how do we go find them and network and bring them in? And so if I was looking at my younger self, it’s just does that person morally? Match like I say this a lot Do I believe that you’re gonna do the right thing and do we generally agree on what the right thing is?

Because you can both be doing something that you think is the right like path right the right way to treat people But at the end of the day, we just have differing views on the world and what is right? And so I don’t know how to it’s a recruiting challenge If I’m trying to place myself at a software company, do I trust those people the idea doesn’t matter It’s do I trust those people because the idea is probably wrong and are we self-aware enough to recognize that really quickly and then together get us rolling down the next path.

So it’s really just a, do I trust those people and gosh when things go wrong, which is never going to happen, are we going to dig up and roll up our sleeves and figure it out together?

Matt: What is your secret for attracting the best talent and getting the best talent to work for you?

Dan: That’s funny. I think it’s Sigstr, especially that early team that we had. It was, AgroDigital was the same. Conor Burt who, was one of the Max’s wingman at Lessonly. He came in as an Orr Fellow, as a biology major. Like those early people that you hire make all the difference in the world.

And again, Connor was a biology major. We hired him and I go digital I didn’t care what he did I just like that dude and I like the way that he solved problems and thought through things and asked a lot of questions and was unemotionally offering great thoughts about and if it wasn’t a great fit he wasn’t you know, but we agreed that hey philosophy of life in general and then let’s just go win together So at Sigstr we always said hey just hire great people and give him green shirts and we’d send them out to wherever our customers were, the HubSpot conferences or whatever else.

And if you had great people, then they would listen to whatever problem you might solve or product you may have.

Matt: How did you get them to work for you though and not some other entrepreneur?

Dan: One of the things, I’ve never said, I’ve never introduced somebody as somebody that works for me. Sure. It’s, we work together.

Yeah. I work with you. Absolutely. And if you’re like and trying to find people that want to lead. And I always want to hire somebody that wants to start their own business. I will teach you, I will show you everything that I mess up. So that you don’t do the same thing. And try, if you find somebody that really wants to own their own business, that’s self-reliant that, that wants to learn that journey then you can just trust that, hey, you can point them at a problem and they’ll come back, not with all the reasons they couldn’t accomplish it, but all the things that they did to overcome those challenges.

And so if you find somebody that’s entrepreneurial and you’re like, listen, I, that’s great. I like the ultimate goal here is that you own your own company and that you see this as a stepping stone to get there. Yeah. And if you treat them well, it’s not like they’re going to leave on day two. You build a relationship and you’re charging through walls together.

And a lot of those people have gone to do their own things.

Matt: It sounds like for you that has really been part of a secret sauce is being that place that’s empowering that desire and need where a lot of companies at least through my experience and hearing through the grapevine, that’s not what they’re looking for, right?

They’re not looking for entrepreneurs. They’re looking for people who are going to be a company person through and through for their whole.

Dan: I, and I don’t mean to bash that at all. Sure. It’s just that’s not how I’m wired. No I’m just I, and then the company’s, I’m trying to get to the heart of

Matt: Absolutely. The magic that you’ve been able to kind of bottle.

Dan: I had I, if when I rewind the clock two years, I was trying to figure out why am I doing this we said the local and the profitable and the, my family understands things but ultimately, what do I really want to accomplish?

I’d like to help 10 people start 10 companies in the last 10 years of my career. Yeah. And I thought that would mean 10 different companies. Not that we could build Haulstrr and then just start doing lots of things around that. But it entrepreneurship has been the most rewarding part of my career. And has allowed me to freedom at this stage to, break away and coach my kids team or go hang out with my wife or whatever we want to do.

So it’s been the most rewarding thing. And I think that there’s incredible people out there that should own their own company and participate in the benefits of that. They’re like maybe the most integral part of whatever company they’re at. And maybe they’re making a bonus, but it’s not theirs.

They don’t have that fire inside them to to run through the walls that are necessary. And if you can help that person, take the first step, that would be, that’d be super meaningful.

Matt: Are there other things that you’ve found that keep. Once you have them on your team, that entrepreneurial person, a lot of times those folks can be scattered in a bunch of different directions. I’m not saying fingers pointed mostly at me.

Dan: Yeah. Yeah. Me too. I remember just, the guys at eight 11 or again they, I was 22 when I joined there. I was 23 when I went opened up the Cincinnati office with some other 22 year old. Awesome. And then I went to Nashville a year later, right?

So I got to be, I got to be an entrepreneur and they gave me rope to like, to go run some things and do some things. And but I still had a safety backup parachute if I needed it. And so I think that’s the key with some of these people. It’s okay, Hey, you want to be an entrepreneur?

Here’s something. Turn this into a business and that’s a really broad and then they’re like, Ooh, how, I was like, I don’t know. What do you think? Let’s talk about it and all of a sudden they’re acting like an entrepreneur. Yeah, and you find out pretty quickly that they May maybe love it or maybe it’s not perfect at this point in their lives Yeah, and so it doesn’t it’s not a surefire thing, but it you know, very quickly giving people autonomy but then having have being a safety net a little bit with the team so That’s what I ran into at 8 11 and in a lot of ways very fortunate to do that and it’s what I’m trying to do now.

Matt: Yeah, sounds like you’re doing an awesome job and it sounds like Haulstr’s really got an awesome trajectory.

Dan: Oh, it’s like everything. It’s a bit of a sausage factory.

Of course. Yeah, of course. But it’s a blast. Again, we work with people we love.

Matt: What’s the hardest part of running a brick and mortar or blue collar business?

Dan: I would say the hardest part of it all is there’s two things that make things really hard. And they’re the two things I love the most technology and people.

Yeah. In this business, I have a lot of customers. We have a lot of homeowners as customers. And then we also have a lot of businesses running under the umbrella with operators and people under those companies. So whether it’s a crew challenge or whether it’s an operator challenge in a certain business or whether there’s, one out of a hundred customers that’s not happy that day and has a big voice online what do you do?

The tech part has been fun cause I we have, we know so many smart people in the tech community. Some good, some bad and then just working through day to day people in tech. Those are the best and the biggest challenges that we have.

Matt: You mentioned living in Nashville, Cincinnati.

Yeah. But when you talk about your business, you almost singularly focused on Indianapolis and Indiana. What is it about Indianapolis and Indiana that…

Dan: It, for me, it is home. It’s where my family is, it’s where my friends are, it’s where my roots are. It’s where I think people have similar values and people are just willing to help.

I think if I could look back at my career, the first pitch that I ever made in my 20s, First tech company. That I go digital is probably certainly at Sigstr. I remember being on the verge or Powderkeg stage and that community of people. And then the companies, the big companies, when I’m an entrepreneur and I call them and ask, Hey, I’m just a guy that’s starting a business.

I’m curious if this makes any sense for you. Would you spend some time with me? I think there’s a lot of places, Boston and the coast, et cetera. Great places. But the businesses are inundated with those types of calls here. I think there’s a mindset of folks in an ecosystem where you get those Yeah.

There’s opportunities. So it’s home for me. Haulstr does have a hospital. There’s Haulstr Detroit. We’ll be in Houston. And that’s just because people are taking us there. And they’ll run it take the framework and run it there, but I’m not leaving. This will always sort of be the hub between here and Bloomington.

Very important to me too.

Nate: As a, you said you’re a right guy who likes to move fast. I think I’d love to know as someone who moves fast, How you manage a team and how you keep them at a startup, especially early stage when you’re running really fast. I think that can be overwhelming to some employees at times.

Yeah. What strategies do you have for founders who might be in similar spots?

Dan: Yeah, I think there’s one, one thing I think that again, goes back to my roots in my early career. And that was Ryan Hasbrook gave me the CEO of Eight Eleven. He gave me his goals one year and three year personal and professional goals.

Just bullet points on a single sheet of paper and I’ve done that with every employee that I’ve ever had is Hey, here’s my goals and rather than say, Hey, give me your goals. It’s Hey, here’s why I come to work every day. And if I’m having a tough day or if I sprint out the side door to go catch my kids games, because the number one thing on my goals is to take care of my family and to be present for them and not miss my kids growing up.

And then when they give you their goals back, and I understand that hey, you’re in Indianapolis, but you, your heart is in Denver or whatever. You’re, your mom, taking care of your mom because she’s been sick. When I see those things then we have more empathy as humans towards one another.

And when we’re running really fast and in the heat of the moment we treat each other a little better. So yeah, it does go really fast and often I have to come back and say, Hey man, listen, I was moving too fast. I’m so sorry. Let’s sit down and have lunch and just make sure we get on the same page.

So just having that balance because I do I’m very aware that whatever pace I’m running at may not be. And other people have things going on, really hard things in their lives and just trying to take time to understand that.

Matt: Why do you think speed is valuable as a startup or as any business of any scale?

Dan: I think time is a fascinating concept in general. We, it’s the only thing it’s the only resource it’s finite. And so let’s get to an answer. Yes or no. If I’m in sales, my goal is to get to an answer. I don’t care if it’s no as fast as humanly possible so that I can go find somebody. I actually can’t help.

So if I have a finite amount of time, what is the greatest neg good that I can produce with that? And how can I make sure that people that are interacting with me, that I’m not wasting theirs? And so whether you’re building a company, we make these things up, we make up companies, right? And so if they’re not taking care of the people that are working in them and the people that you interact with every day, then let’s go make something else up and let’s get to that answer really fast.

I know you’re a big music guy.

Dan: I am.

Matt: Are there any albums or is there one album that you can think of that got you through either some dark times on the Entrepreneur Roller Coaster or some really exciting? Fast moving times.

Dan: I love it. I love that question. I listened to Sturgill Simpson a ton.

Yeah And that’s a guy that you know had success and is now disappeared. Yes. He has a family. Yeah And I think that comes through in some of his lyrics and in tunes in general, so I always have music on I’m always on Spotify and Mornings, I got this playlist called mellow moods and the rest of the day.

It’s a mix of everything from rap to classic country to classic rock

Nate: Pump up song, you’re about to go in and close the biggest deal of your lifetime the biggest small chorter that you’ve ever had What are you dwight shrooding in the car before you go in there?

Dan: That’s a great question. I made my My, my sixth grade son, a a hype mix.

That’s right. Things like Thunderstruck or Eminem and I don’t know, but the same stuff, Guns and Roses, I don’t know. Some crazy rap rock and roll Led Zeppelin. I love myself some Led Zeppelin.

Matt: Do you have a one book that you recommend to entrepreneurs more often than not?

Dan: I like stories. I don’t like business books. I like stories of people. Things like let my people go surfing. The founder of Patagonia, I don’t even know his name, but the one Nate and I talked about recently is it’s the easiest read in the world and there’s lots of pictures. Not, that’s why I read, not why I recommended it to Nate.

But it’s one of my favorite books because it talks about the life is good journey and community driven company that built an incredible culture that gives back that is just but they talk about I don’t know if you remember Galleons in Indianapolis. Oh, of course. So Galleons was like Dick’s sporting goods or Academy sports or whatever.

And they were trying to get their life is good shirts in there and the Galleons guys were like, Hey, come on to meet us in Indianapolis. And these guys were in Boston and they’re like we don’t have enough money to get there. What do we do? Like, why don’t you guys come out here and see your operations, which was run out of their apartment.

And they serve these guys from Galleons, these execs from galleons, like spaghetti, like ragu sauce. And they had the time of their lives and Galleons bought all their stuff and it like changed the trajectory of their company. So hearing those stories and how they built a brand and a culture. To persevere through all the weird times. Like I love that book. It’s in perspective.

Nate: I don’t, I usually only go audio books. There’s no audio book of life is good. Cause there’s so many pictures, but he recommended it. So I was like, you know what? I’ll do it. And I could not put it down. It was so good.

Nate: Like it just talks about, Oh, it’s just great stories.

Matt: And that’s what it takes to get you to read an actual book. We got to get some picture books.

Nate: I told Dan this, I told Dan this, the final chapter. Brought me to actual tears. That’s amazing. It was that moving and like these guys care about their business and their mission, not even their business, their people and the mission and the community.

So much that it, I actually, like I cried, it was that good. It was incredible.


Matt: Strong recommendation. I’m telling you it’s a great book. Five stars in a tier. Yes. Through Igoe Digital’s software probably. Yes. I love it.

Dan, this has been an amazing conversation. We have a couple minutes left and we love ending the show with….

Nate: My favorite part of every show is yes, the lightning round. Okay, so for the lightning round It’s just top of the brain quickest thing that comes to your mind I’m gonna ask you a couple questions here and we want to hear your Lightning quick answer.

Dan: I like it.

Matt: There’s no wrong answers.

Dan: Okay, we’ll see

Nate: So outside of the amazing entrepreneurial ecosystem, what is Indiana known for?

Dan: Racing?

Nate: Boom. That’s that’s a frequent answer. I will say that’s a good one.

Dan: Tenderloins.

Nate: Oh, not a frequent answer, But my favorite answer.

Matt: That’s the first

Dan: The Golden Ace.

Matt: The Golden Ace. Yes. You’re a Golden Ace guy. I love these.

Nate: The McGinley Pub

Nate: Awesome. Alright. What is one hidden gem in Indiana?

Dan: I used my Golden Ace answer. Yeah, you did. I’d say Fort Harrison State Park. It’s in my backyard and it’s how I escape. Nice.

Nate: Yeah, and it’s like pretty close. You don’t have to get too far, but there’s a lot of good trails there.

Yep. Who is someone we need to keep on our radar? Someone who is doing big things.

Dan: Matt Moe. Yes! I love myself some Matt Moe. Yes! So he was an Orr fellow, total badass. When I had that little side gig at iGoDigital, he was my, they gave me Matt. And we had a hell of a lot of fun. What is Matt up to these days?

Matt is, he’s thinking a lot. Yeah. I’ll leave it at that. Okay. He’s thinking,

Nate: I love that. Matt Moe and I just ran a triathlon together. Matt did the triathlon with you? We were up. We were up in culvert. Not the Ironman. Not the Ironman. I did a, we did a short one up in culvert, I was gonna say.

And he had been texting me, he was like, dude, I’m doing, this is my first ever triathlon. Yeah. And we got outta the water exact same time we get on the bike. We were just churning away. I’m like chit chatting the back. ’cause I’m just having fun and I’m just like, he was like, oh, that was so fun. He zooms past me at the last second on the bike.

No, beats me by probably 30 seconds. And I’m like, oh Matt, it’s gonna be like that, isn’t it? ? So I. I just haul right out of the run and he never looked back to catch him. Oh, I ended up passing him. Yeah, I was like, Oh, I thought we were gonna have fun. But no, he’s so great.

Dan: Yeah, he’s great. He again, I there’s just so many people and men, that I’m always trying to work with.

And Matt’s, whether it’s now or 20 years from now you only have 10 years left of the career though. I don’t know. Maybe I’ll farm together with him or something.

Nate: Yes. Okay. Final question, right? You already gave us the golden days. So if I asked you, where do you go to unwind?

Dan: The woods, Bloomington Lake Monroe. Yeah. Anytime I can get outside that makes me, recharged.

Nate: I love that.

Matt: Me too. Dan, that was a great conversation.

Dan: Guys, you rock.

Matt: Thanks for everything you do. Thanks for coming in here.

Matt: This has been get in a powder cake production in partnership with elevate ventures, and we want to hear from you.

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