How To Go From Zero to One With Serial Entrepreneur Dan Hanrahan

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 Hunter CEO at Powder Keg 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 Powder Keg and on the show today is Dan Hanrahan co-founder of Hollister just the scrappiness and the perseverance to do what has to be done today in order to get some tomorrow [Music] Dan Hanrahan is the co-founder of Hollister an Indianapolis based Home Services Company he was a previous partner at iGo digital which sold to exact target and was then of course acquired by Salesforce he's also the founder of sixter which was acquired by Terminus and he has been doing some really interesting things in entrepreneurship via acquisition we're going to talk all about that today as well as Dan's story Dan welcome to the show thanks for doing this thanks for having me guys so excited to 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 Hollister 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 it's a good question it may be serendipitously my first jobs happen to be with really small businesses my first job I was 16 and I was building retaining wall so I weighed like a buck 10 and I had retaining wall stones that were about 90 pounds awesome and the two guys that ran the company country the the company they were in machines while I was doing my best to build a wall so yeah I I what one just random story from there I remember I didn't know how to drive a stick they had 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 so I didn't seek it out it just it just came to me and I realized that boy I'll ask 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 what do you think was the number one skill or strategy that you learned in that first job probably just grit it was a hard job and those guys were smart guys that 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 were you always a founder like you know while you were working there or were you still like coming up with ideas or do you have a high school hustle like every kid in high school I was always uh coming up with great ideas uh putting him into action I don't think I did a lot of that in high school right I was running around playing sports and uh gosh I worked in the you know Pizza world and all those kind of classic like high school jobs I mowed some Lawns and things like that but I didn't really really get that entrepreneurial itch until maybe when I was 16 I had that job and then majored in entrepreneurship in college and and what is it like to major in entrepreneurship at IU the the school was fairly new it was entrepreneurial in itself so I think it's like super established and robust and 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 was Dr hay really teaching back then oh yeah entrepreneurship school he was awesome there were good days we had a lot of fun yeah he really is the man just by the time I was at IU I was in the entrepreneurship program as well Dr K was there and it was a real program by then yes but haberly still had the 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 ten other entrepreneurial students in the his basement yes and he's I prepared these fictional case studies and he just loved it we would just go through them and then like you'd get like almost to the end of the case study and you'd be like what actually happened was in this fictitious case study you know they were all like real scenarios that he had been through absolutely that's really cool you got that exposure I actually went and knocked on the door of the entrepreneurship program it was probably two thousand oh gosh 2012.

so after I go had sold to exact target we bought a little piece of land down there and started building a log cabin and awesome 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're like who are you and why are you 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 him oh I tried to guide them to somebody real that could help no way 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 you found yourself like repeatedly giving the same advice on a 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 yeah 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 wing woman to cover your blind spots and you don't need to 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 what was the first real Venture that you started 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 Hasbrouck and Jeff Weiser in Ryan's basement on North Waldo Avenue to build a I.

T recruiting Staffing business 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 the work companies like 3M it's 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 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 yeah and have write down their hours and have their manager sign it and fax it to us oh my God so I can revolutionize this yeah there's got to be a better way probably the easiest problem to solve in the world so the brook Source guys said actually even before that I said hey I'm going to start a software company I gotta go do that thanks for everything 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 Head header on that paper is Bush light night we got some Bush lights that's great 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 ten thousand dollars 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 yeah 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 giving that person no guidance uh my requirements were garbage and so I came back three months later it was not his fault he's a great engineer it's 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 do you have good advice for non-technical Founders like practical advice for non-technical Founders working with ctOS technical people yes well 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 it 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 and he had such a great track record of success I know Matt gradwell 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 yeah 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 the mandwell 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 in fact in the problem 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 oh yeah in that person are the things that you did to help develop that trust because I'm assuming you know about as much coding as I do which is yeah you can maybe follow directions and make an app if you follow step by step and have lots of tries at it maybe maybe so how did you develop that trust with Sam or any of your other technical leads as you develop different businesses yeah it's a really good question I I think having them on the phone listening to customers yeah 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 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 asks that question is 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 dad I would say you're an idea guy right yes like a lot of ideas yes you know yeah so like coming in there I can just imagine you in one of those first like product meetings he's got to do this and it's got to do this and it's got to do this they're like all right you get to pick one for the next month right yes but I'm also very aware of that flaw or whatever superpower superpower depending on how 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 did I just freak you out yeah because listen these and I 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 in in progressing those conversations before it distracts somebody that is actually making progress on what we really need to do that's I 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 I I think the key is as we say this all the time in order to get to that stuff we've got to survive yeah in 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 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 how did that work at iGo digital those early days this is a funny story there's this guy and I will name him because he'll tell him this all the time so Ryan Hughes Ryan went on to have a nice career at exact target in Salesforce and and is is still doing really cool stuff great sales guy we plucked him out of college and I go digital uh 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 the customers like do not recommend any adult costumes with the kids costumes you 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 uh so that is like a super Scrappy thing that's amazing so Ryan's career in text started by uh searching for hot pants products you're like I don't know the machine can't do it so let's find a person and then we'll figure out how to unmate the stuff later yeah The Wizard of Oz approach right you gotta have the the person behind the curtain making sure that things are curated making sure things work the way the customers work that's probably not on Ryan's resume but he'll laugh that's a great example that's a great example so that was the next after your the time card yeah 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 amazing but anyways last piece software we we it was just a ratings and review system what's 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 I was trying to sell him ratings and reviews for his batteries website I was like ratings and reviews will change your battery's 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 the recommendation engine and so we put those two companies together that became I go digital we ran that from 2008 to 2012 sold it to exact target I stayed as 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 then 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 what about it was beyond your comfort zone 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 sixster is there was a ancillary product of the data of that business and I was able to take that data and try to drill that into a second product before before we were acquired so that was a lot of fun and that allowed me to scratch that edge for a year without just running out the door 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 yeah I say this every now and then I'm a down into the right guy I think everybody wants to be up into the right if time is on the x-axis and value is along 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 adds value I love that process the iterations involved in it and just going fast so in my current company that Hollister we were able to do that and I was 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 when I get comfortable uncomfortable with as the business grows then they're more equipped and able to step in and run the things starting companies we have a bit of a almost like a venture Studio yeah it's weird I never thought that Hollister would be that but literally mulch mulch fundraisers is what holster started as yeah so taking Tech and applying it to Super non-tech businesses mulch Christian Anderson another high alpha guy said this really well he's hey I can't be the best a digital marketer in the world he said I can maybe be the best digital marketer venture capitalist 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 like we'll start a new car yeah yes so that mulch business took off and then I'm able to get into the next one we acquired a little patio company and plugged that into the sort of e-commerce customer acquisition model the back office stuff that we had built with holster and then we were 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 we help on the business side drum up customers and pay taxes and things like that yeah so that's where it's evolved and again it's just getting comfortable when I was at exact target 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 sales force 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 yeah Salesforce and I was like so do you want me to sell or do you want me to try to figure be in the CRM and just go sell yeah there you go you had your wing person there since she was good at process and I understand the importance of why that had to happen in a bigger company but I wasn't patient or mature enough to slow down and do that work on my own one thing I'm noticing as you talk about Hollister in the business you have today none of the companies I would categorize as software companies no not at all I so I after 60 was acquired by terminus I wrote down to Nate's point I had 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 wanted to be local not that it has to stay local but it has to be run locally in brooksource they could start or 811 they could start a staffing arm in Cleveland but they 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 in another city great I wanted to be profitable um just so that the business could do what was natural for the for the business and then we fi if not that it can't ever be funded but if we find that inflection point where we can pour gas on it yeah then then great we can go fund it and I wanted my family to understand what actually did it like connect some dots with my family so my mom was always like hey he's in software he could probably fix your computer yes yeah yeah 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 like thought that we still sold like discs like CD-ROMs yeah 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 were on we're dating ourselves yes yes not me he has no idea although I did buy Nate a record player so he is a vinyl guy I am a vinyl guy I am a vinyl guy I have two records I have Chris Stapleton and I have Zach Bryan oh actually three and Elvis and Elvis yes collectic absolutely he's gonna collect a guy good work Matt are you ready to transform your brand with award-winning video content that captures your vision and connects with your audience check out Alchemy the experts at building your brand using video from story driven social media Snippets that leave a lasting impression to compelling full-length documentaries they have got the expertise to take your brand to the next level Alchemy is actually our video partner here on get in and they do amazing work all the videos across social across YouTube all that is done by Alchemy and they're an amazing partner to work with reach out to me Nate at Powder Keg or check out alchemefilmco.

com to get connected with Alden and his team they will take care of all of your video needs 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 yeah the beauty and I'm so grateful for the time in SAS in Indianapolis that that journey and and the fortunate timing to to be launching sigster 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 an MBA on steroids because Tech has been so analyzed right the the unit economics of a SAS company and and how you value SAS 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 uh millions of businesses right there's 10 trillion dollars 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 hasn't applied Tech and then I'll just apply Tech and then we'll grow it and and then we'll make it more valuable and then we'll sell it so the holster in a lot of ways is the tech sort of thing to drive e-commerce and operations uh 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 you name the 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 a fascinating leading 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 cash like all this kind of stuff and she's she was just like wow and she's like 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 and business in general understanding where the business value is created and what makes an Enterprise valuable over time yeah and so you're able to identify those things that are the hard things right to manufacture out of nothing right and if you can go and find those quote unquote hard things that are hard to manufacture from nothing sure but then apply the things that for you are easy because you've built them out at Hollister and you've done them how to use software how to use a CRM how to use good digital marketing 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 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 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 and some of the things that I never got the opportunity to do there's not I I've never run a sort of crowdfunded thing and like the kickstarter campaign so I've got an idea that I'm dying oh and do that with so there's just product-led growth yeah is is another one there's a few itches that I've always wanted to see those holster signs all over the place man that's like product let it grows poster 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 is the next big thing in marketing and I was like Direct Mail and they just made fun of me but I explained why it's because you're not wrong we we forget like we we're emailing or 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 what are so I mean you're Matt called them brick and mortar businesses I like the term blue collar blue collar business 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 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 Kerry came from Tech here in Indianapolis uh 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 CEO 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 uh Beach head approach right and so what what is in a neighborhood every day the thing that we all started like half the people on the podcast probably said there was her first entrepreneurial thing mowing yeah so we'd get 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 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 holster and they'll be in the neighborhoods every day so if something else happens we can cross-sell right yeah 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 the local service provider to compete with the national brand and so I'm also so very interested in solving that problem we've got it 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 is my biggest asset probably and I don't know what the heck to do with it nine times out of ten 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 who knew that Indianapolis was going to be the Home Services Capital right this is like a V2 of that right yes it is uh obviously Angie's List I have a ton of respect for that business um as a homeowner um I I think there are other ways to approach that challenge that helped not only a homeowner but also the service provider in the local approach that you're taking to it right hyper local like Indianapolis that's where you started and 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 kids game or my kids school or whatever that person that woman 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 roll-up 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 business value Community Driven yeah trusted been around a long time right and done things the right way if I look at 8 11 that was just such a lucky place to land shoot though 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 I 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 might be a couple hundred thousand in profitability Not Top Line but profitability and but have built that it's an amazing lifestyle business but it 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 I 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 may be some weird way 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 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 it's a good question and I think it it I don't think it's function of age it's a function of experience and it may be a bit of both right when I'm 20 20 I have I I probably might 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 that I than maybe acquiring a business that already has cash flow 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 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 of course but it the business I'm looking at are pretty small so let's say it's a a business doing a couple hundred thousand in profits in cash flow typically something like that might be two to three x profits right it's not SAS it's not top line revenue multiples it's two to three X on the cash flow yeah so if you think about that if I Acquired and I don't even grow it in two to three years I have the I paid for it yeah 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 mean 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 uh lots of other things so you you can you can buy a couple hundred thousand dollars in cash flow every year with with no more than 50 Grand and there's a lot of ways to go find fifty thousand dollars 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 and maybe I have kids now maybe I've got a mortgage 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 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 gonna at the end of the day I can't how many times have we all done this whereas man I did such a great job and then the company got all the 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 a part of it if there's a bad outcome you're like I gave it hell I 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 it is another way to have skin in the game do you think that mindset is what made you unemployable we haven't talked about that a little bit before 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 here's a problem here's how to solve it and let's talk every day about my path to solving it and if if there are projects that that can be run autonomously and things that just need to be solved and and don't have to rely on the entire team of the organization to be distracted from whatever the the primary objective of the businesses I enjoy those but I'm not very good at uh coming into a larger business and and filling a role so 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 the the luckiest thing that happened again with 811 is they were recruiting business so all day I interviewed people and tried to match them with the the hiring manager at the end of the day I'm I'm not very good at anything but I'm good at building teams and saying okay shoot my product hat 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 going to 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 how 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 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 always going to happen are we going to gonna dig up and roll up our sleeves and figure it out together what is your secret for attracting the best talent and getting the best talent to work for you that's funny I think it sticks your especially that early team that we had it was I go digit was the same Conor bird who was one of the Max's wingman at lessonly he came in as an ore fellows biology major like those early people that you hire make all the difference in the world and again Conor is a biology major we hired him did I go digital I didn't care what he did I just like that dude and I like the way that they solve 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 sixth year we we always said hey just hire great people and give them 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 how did you get them to work for you though and not some other one thing 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 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 ever I will show you everything that I mess up so 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 that's great I 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 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 right through and through right for their whole I I don't mean to bash that at all sure it's just that's not how I'm wired no I'm just and in the company I'm trying to get to the heart of it absolutely the magic that you've been able to kind of bottle 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 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 holster and then just start doing lots of things around that but it entrepreneurship has been the most rewarding uh part of my career and has allowed me to Freedom at this stage to 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 are there other things that you've found that keep that person engaged 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 yeah yeah me too I I remember just the guys at 8 11 are again they I was 22 when I joined there I was 23 when I went and 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 oh wow 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 uh you know very quickly giving people autonomy but then having have being a safety net a little bit yep with the team so that's what I ran into at 8 11 and and in a lot of ways very fortunate to do that and it's what I'm trying to to do um now yeah sounds like you're doing an awesome job and it sounds like Hollister's really got an awesome trajectory 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 what's the hardest part of running a brick and mortar or blue collar business 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 because 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 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 makes this place home well it for me it is home that's where my family is it's where my friends are it's where my roots are that'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 first tech company at iGo digital is probably certainly at sigster I remember being on the verge or powder keg stage yeah 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 we just spend some time with me I think there's a lot of places Boston and the coast et cetera are great places but the businesses are inundated with those types of calls here I think there's a mindset of folks and an ecosystem where you get those those opportunities so it's home for me holster does have a there's holster Detroit we'll 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 as a you said you're a day one down to the right guy yeah he 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 and you know at a startup especially early stage when you're running really fast things that can be overwhelming to some employees at times yeah what strategies do you have for Founders that might be in similar spots 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 Hasbrouck gave me the CEO of 811 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 hey here's my goals and and rather than say hey give me your goals okay here's why I come to work every day and if I'm having a tough day or I Sprint out the side door to go catch my kids games because the number one thing on my goal is just take care of my family and to be present for him 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 your mom taking care of your mom because she's been sick or 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 why do you think speed is valuable as a startup or as any business of any skill I think time is a fascinating Concept in general we it's the only thing it's the only resource that'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 net 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 cup 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 I am are there any albums or is there one album that you can think of that got you through either some dark times on the entrepreneurial roller coaster or some really exciting fast moving times I love it I love that question I listened to Sturgill Simpson a ton yeah uh and that's a guy that you know had success and has now disappeared because he has a family yeah uh and I think that comes through in some of his lyrics uh and and Tunes in general so uh I always have music on I'm always on Spotify and morning so 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 pump up song you're about to go in and close the biggest deal of your lifetime the biggest small shorter that you've ever had what are you Dwight schroeding in the car before you go in there gosh that's a great question I I made my my sixth grade son a a hype mix that's great things like Thunderstruck or Eminem and I don't know but the same stuff Guns and Roses I don't know some crazy rap something on rock and roll Led Zeppelin I love myself some Led Zeppelin do you have a one book that you recommend to entrepreneurs more often than uh not 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 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 exactly why you recommended it but it's one of my favorite books because it talks about the life is good journey a 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 gallions in Indianapolis oh of course so gallions was like Dick's Sporting Goods or Academy Sports or whatever and they were trying to get their life as good shirts in there and the galleons guys were like hey come on to meet us in Indianapolis and these guys are 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 served these guys from gallions these execs from galleons like spaghetti like Ragu Sauce and they had the time of their lives and gallons bought all their stuff and it like changed the trajectory of their company so hearing those stories they built a brand in a culture persevere through all the weird times like I love that book it's in perspective I don't I usually only go audiobooks there's no audiobook of life is good because 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 so good it's an easy reason like it just talks about oh it's just great stories and just that's what it takes to get you to read an actual book picture books 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 cared 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 it's a strong recommendation yeah exactly five stars in a tear yes three I go digitals 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 my favorite part of every show is 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 going to ask you a couple questions here and uh we want to hear your lightning quick answer I like it there's no wrong answers okay we'll see we'll see okay outside of the amazing entrepreneurial ecosystem what is Indiana known for racing boom that's that's a frequent answer I'll say that's a good one oh not a frequent answer but my favorite that's the first actually the golden Ace guy the McGinley all right what is one Hidden Gem in Indiana I used my golden Ace answer I'd say Fort Harrison State Park it's in my backyard and it's how I escape nice yeah and it's like pretty close so 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 Matt MO yes I love myself some Matt Mo yes so he was an orfellow total badass when I had that little side gig at iGo digital 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 I love that I just ran a triathlon together after the trash we were helping we were up in Culver not the Iron Man not the Iron Man I did a we did a short one up in Culver and he had been texting me he was like dude I'm doing this my first ever Triathlon yeah and we got out of the water exact same time we get on the bike we were just churning away I'm like chit chatting in bed because 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 about probably 30 seconds and I'm like oh man it's gonna be like that isn't it so I I just haul right out of the run and he never look back did you catch him oh I ended up passing him yeah I thought we were gonna have fun but no he's so great yeah right he's great he again there's just so many people and then that I'm always trying to work with and and the mats 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 yes okay final question right you already gave us the golden Ace so if I asked you where do you go to unwind the Woods Bloomington Lake Monroe yeah anytime I can get outside that makes me recharged I love that me too Dan there's a great conversation guys you rock thanks for everything you do thanks for coming in here this has been get in a powder kick production in partnership with Elevate Ventures and we want to hear from you if you have suggestions for a guest or a segment reach out to Matt or Nate on LinkedIn or on email to discover top tier tech companies outside of Silicon Valley in hubs like Indiana check out our newsletter at powderkeg.

com newsletter and to apply for membership to the powder cake executive Community Check out powdercake. com premium we'll catch you next time and next week as we continue to help the world get in since you just listened to this podcast you might be thinking about starting one for your company lucky for you our partners over at casted have you covered cassid is the first and only podcast in video marketing platform made specifically for B2B Brands I love this about them the platform makes it possible to publish Syndicate amplify and measure the value of your podcast and video content in fact we use it for our podcast here at Powder Keg and if you're a startup you should listen up because cassid for startups is definitely for you they are offering exclusive deep discounts of up to 82 percent off retail price for qualifying startups connect with casted at casted. us slash powderkeg