In the fast-paced world of entrepreneurship, where innovation and perseverance are the keys to success, few stories are as inspiring as that of Courtney Guertin. In a recent episode of The Dealmakers’ Podcast, Guertin shared his remarkable journey from a curious college student to a successful entrepreneur.

His story embodies the spirit of determination, growth, and adaptation that characterizes the modern startup landscape. His startup, Ease, has attracted funding from top-tier investors like Centana Growth Partners, AWS Impact Accelerator, Google for Startups, and Spectrum Equity.

In this episode, you will learn:

• Embracing new experiences and following your curiosity, as they can lead you to unexpected opportunities and passions, and seizing opportunities to gain experience in different industries and domains that can shape your entrepreneurial journey down the line.
• Not being afraid to take risks and stepping out of your comfort zone to pursue opportunities that can accelerate your growth and learning.
• Embracing innovation that often involves trying different ideas, learning from failures, and leveraging emerging trends to create successful ventures.
• Tailoring fundraising efforts to the business’s growth stage, and seeking investors who share your mission and values.
• Effectively communicating your vision, setting clear expectations, nurturing a motivated team, and accepting that constraints can foster creativity, efficiency, and resourcefulness, leading to innovative solutions and outcomes.
• Understanding how repetition helps ingrain important messages within your team, customers, and stakeholders, leading to greater understanding and alignment, and remaining open to unexpected opportunities, partnerships, and acquisitions that can elevate your business to new heights.
• Entrepreneurship is a journey filled with twists and turns, and success often requires a blend of ambition, adaptability, and patience.

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About Courtney Guertin:

Courtney Guertin is the Co-Founder and CTO of Ease. Courtney has a long history of working in software development and technology consulting.

Courtney founded Courtstarr in 2006, which provided technology consulting and web development services to its clients. In 2008, they began working as an application architect for SoftBrands before joining Digg in October of that year as a software developer.

At Digg, Courtney assisted in developing one of the largest Facebook Connect integrations at the time of launch, the Digg Ads and Digg Content Ads platform, publishing tools and widgets, writable API, web, and internal analytics.

In September 2010, Courtney co-founded Kiip, where they served as CTO until December 2014. Since then, they have been focusing their efforts on Ease, which they co-founded in 2015.

Courtney Guertin received their Bachelor of Science in Computer Science from the University of Minnesota. Courtney also has an Associate’s degree in Japanese Studies from Akita International University.

Connect with Courtney Guertin:

• Linkedin
• Crunchbase
• TheOrg
• PitchBook

Read the Full Transcription of the Interview:

Alejandro Cremades: Um, already hello everyone welcome to the dealmakerr show. So super excited about the guest that we have Today. He’s done it multiple times and they also successfully so you know the last one you know just went through a really interesting merger. But. We’ll get to that in just a little bit but again, you’re going to find it super inspiring so without farther ado let’s welcome our guest today kurtnie gerting welcome to the show. So originally you were born out of Minnesota. You know it sounds like you were there quite a bit.

Courtney Guertin: Hey thanks so much Ilejandro Thanks for having me.

Alejandro Cremades: So give us a walk through memory lane. How was life over there.

Courtney Guertin: It was good. Yeah, so grew up in Minneapolis minnesota or just north I went to after high school didn’t quite know what I wanted to do ended up doing community college and then um, found myself at University Of Minnesota did i. Ah, study abroad to Japan and it was that trip that kind of made me land on computer science. Um, and so I was inspired by reading wired magazine you know, ah different programming books. But and that trip just talking to people abroad. Through like the internet was this really surreal and I was fascinated by um, the culture there in kind of the tech forwardness of that area and so when I came back to the University Of Minnesota I decided to go all in on computer science ended up graduating worked at a small company. We did vertical crms one for the financial industry 1 for real estate and one in healthcare and that healthcare one ended up kind of ah early seed it grew into something that kind of stayed with me in my later life and was ah the genesis of my last company.

Alejandro Cremades: Amazing. So so one of the pivotal moments was definitely working a dig. So how do you land? you know a dig.

Courtney Guertin: Yeah, so this was 2006 I really wanted to kind of Silicon Valley was sort of calling my name in a way but I didn’t I didn’t initially move. Um I was a little bit. I guess fear was this was there I just bought a house in Minnesota felt I was rooted but I had a couple friends that moved out there 1 of them. Leah Culver who’s a great engineer and she’s done things and sold companies to Twitter and things. Um, she went out in 2006 and started building a lot. Networking a lot doing very exciting projects that gave me the motivation to kind of say hey I really need to go do this and I finally did so in 2008 and I wanted to live in work in San Francisco and so there weren’t that many companies at the time in San Francisco um so I applied to stumble upon and dig I got offers by both I chose dig and um, it really set off an incredible network of people of very interesting company at the time um, trying to pivot into some not pivot. But.

Courtney Guertin: Rebrand themselves into something stronger and I met lifelong friends and I I learned a lot from building architecting scaling businesses or scaling. Ah you know feature sets and that gave me the confidence then in 202010 to venture out on my own.

Alejandro Cremades: Um, so let’s talk about that you know venturing out on your own. What happened.

Courtney Guertin: Yeah, so I had a few ideas. Um, one of them was ah a project that called follow style it was in a pre-pinterest we did curation and fashion decor and things at another one where I was this 8 bit avatar called 8 bit. Um. Kind of hit the scene and and 20 ah started in 2010 got a little bit bigger and in and 2011 um on Twitter with tech Twitter later became an nftt project for kind of a fun thing on the side. Um I also created a mobile game you know mobile app development was was ah. Peaking my curiosity in in that I collaborative with a friend and we did some kind of a tweak on mobile advertising because we thought it sucked at the time people were putting small banner ads everywhere and so we did rewards for virtual achievements and real rewards for virtual achievements created a company around that. I mean it was called keep and that we hired a really amazing early team and that was a fun adventure from starting in 2010.

Alejandro Cremades: Um, so with keep what was the business model. How are you guys making money.

Courtney Guertin: Yeah, So it’s kind of a double sided Marketplace This is um before Programmatic advertising came in in a big way and so we found games or other applications that had basically moments where and. Ah, their customers were really engaged maybe beating a level or or getting a high score or completing a to do list in those moments we would offer a reward. It could be virtual currency in that app or it could be a real award like you get done running in my fitness pal And. Ah, propel could give you a powder pack that you could claim and go to a store and redeem and so it was brands being there at your highest moments of achievement getting you rewards and it was just a different kind of mobile advertising engagement play and it was.

Courtney Guertin: We we had a Bd team that would go out and talk to all these debs and then we I was on the cto um the Cto and so I built a tech stack and basically what we ended up doing is scaling the kind of the rewards inventory.

Alejandro Cremades: Um, and how much money do you guys say raise for that company.

Courtney Guertin: Um, total we raised ah $32000000 from 2010 to I think it was 2016

Alejandro Cremades: And you’ve also yeah mean you, you’ve raised quite a bit you know, throw your journey money from bc you know over a hundred millions I guess what are some of the things that you’ve learned from ah you know dealing with venture capitals.

Courtney Guertin: Yeah, well one, you definitely need to have a process so and and so you know typically I think the traditional thing would be you kind of create your target key key partners. You know your your personal tier 1 tier 2 tier 3

Alejandro Cremades: Are.

Courtney Guertin: You have to really um polish your pitch and it’s different at each stage. You know the earliest stage its its team its vision. Its energy. Its are you doing something? um that you feel you have an unfair advantage in um, ah and. Then it just becomes very metric based you know after series a and and so do you have the right metrics and you have to find people who may or may not um, you know for example, you might have to go a p route if you’re not a private equity route. If. You’re not growing at the multiples that like perhaps in Adreessen Horowitz would look at so you have to adjust your thinking and pray perhaps targets depending upon your business and the scale of that business.

Alejandro Cremades: So what have you also experienced you know between bootstrapping like you’ve done with other projects to. For example, you know raising money the way that you guys did it with keep.

Courtney Guertin: Yeah, so with with with ease my last company. It actually started out as a side project. Um I as kind of mentioning I met my co-founder in Minnesota when I was we did that cr m for the health care industry. And he was an insurance broker by trade but very tech forward meaning ah trying to adopt anything technology to help his business grow and so I chatted him about different feature sets products. You know, got doing customer research and we hit it off? well.

Alejandro Cremades: Um.

Courtney Guertin: Well, ah while I was out building and working in Silicon Valley he um he left the insurance industry and kind of worked on tech plays to help insurance brokers leverage technology and he realized that he couldn’t um, do it with off the-shelf software products. Catered to larger insurance brokers he wanted to help the small medium businesses and the insurance brokers that helped those businesses and so he contacted me and this was roughly like June to 2012 saying hey I need I need a platform for this. You know the smaller kind of broker. Ah, that helps customers that have employers from 2 to 500 employees and he had a couple contractors and a couple quotes I gave him some feedback and I gave them kind of like hey option a probably won’t work option b could work but I’ll give you option c. You know and this is where I came in I said I’ll do this on the side. Um I know a lot about this industry I’m excited about it and we came up with an agreement and so that I started my nights and weekends doing this because I really wanted to make about $5000 a month. And I figured I could do this as a side hustle to do that and eventually um I told him I would you know deliver kind of the first version and ah around ninety days and then he was a very good salesperson had a very good network as.

Courtney Guertin: You know I think as you you and a lot of your previous guests. Ah are aware distributions everything and so he had ah a really good. You know sales ecumen and and had a good network. So after the Mvp was created about ninety days later we were ramen profitable. And so it had immediate product market fit. So my side project turned into a lot of late nights and all my weekends I eventually had to make a decision on continuing with with keep or going all in at ease and after about 4 years I decided to call in on ease just because I thought.

Alejandro Cremades: Are.

Courtney Guertin: That it would be too much of a missed opportunity to not throw myself at it a hundred percent of the time.

Alejandro Cremades: So now in this case I mean what did having immediate product Market fit look like.

Courtney Guertin: Yeah, so really, it came in is once we? Um, we had a big vision for what ease could be and just for some background ease is a employee benefits platform and you can think of it as a a zen. Or augustto rippling or namely but through the traditional insurance broker. So a traditional insurance broker they have lots of clients already and but they don’t have technology so’re dealing with paper fax excel lots of different web portals. We do all that in in 1 platform. So we combine. Employee benefits management onboarding payroll connections care connections on 1 and our goal was hey if we we get the broker’s trust they will onboard all of their clients and we don’t have to knock on the door and have a huge sales team. Trying to call all these employers. The brokers will just do that for us and if we needed to make the platform easy to use and hence why we called it ease took me a couple years to get the domain name ease dot com but finally did it I was proud of that moment and the. And what immediate part market fit was we had big goals and dreams but we started really small. We started with the state of Minnesota and every employer when they want to do? What’s called medical underwriting. Let’s say they got a ah big increase in their their rates.

Courtney Guertin: For the year that’s their company of 10 employees. They get a big great increase. It’s going to be very expensive next year to continue with the same carrier what they do is they have to go and fill out like four different health applications for the 4 different carriers in Minnesota. It’s very tedious very time consuming. A noise employees because they’re filling out the same thing 4 times we basically package that up so an employee could do that once the broker would be aware. We’re getting rid of all the paper you know and we make sure that it’s filled out accurately and legibly. And that all then at the end of the experience. It’s like a docusign you know you go fill it out once all 4 forms are presented to you. You can review them and sign you’re done streamlines the process immensely. Well we started with just that that feature set alone and. The product market fit feedback was people loved it and they kept asking for more features immediately. So they they use it on 1 group they wanted to use it on another but they demanded hey I need you to do x though I need to do y I need all these different feature sets. So when you have someone. Wanting to reuse it but pretty much demanding that you add a lot more functionality you kind of know you got something so they’re excited to use it but they wanted more and so we gave them more over the over a couple years of bootstrapping we got to a million in revenue and again this is all on the side. This is just me.

Courtney Guertin: Ah, working in San Francisco in the evenings. My co-founder at the time ended up being in Las Vegas and it was just like a couple of us jamming away.

Alejandro Cremades: Um, so then how did you guys go about racing money as well For this How much have you guys raised today.

Courtney Guertin: Yeah, total was $68000000 um, it really started out with the following Zeni came on the scene and they did something really? Ah, ah, they lit a fire on the whole hr in short text space. They raise a lot of money and they use that money to call every employer in America and basically say hey your current broker sucks. You need to use our platform. Everything’s all in one solution and that made every employer talk to their broker and and say hey. Um, do you this company’s and if it’s calling. Do you have anything that does everything online. They went out searching for it and they found ease so we started getting a lot of calls um from players and so we couldn’t really meet the demand that we knew was coming so. Bootstrapping gives you a lot of flexibility but you grow slower if you’re just using your profits. We knew that because of the war chest that zennifi has we’re gonna lose and miss an opportunity if we do not also try to grow faster. So in 2015 we set out to go raise money? um. And I thought because of my connections that it was going to be easier, especially because we already had a lot of revenue and we’re profitable and I was I was wrong I I my first 2 people that I thought were like shoe ins on investment said no and they said no because we were.

Courtney Guertin: Remote I was in San Francisco my co-founder was in Las Vegas um he’s not a traditional you know tech person. He’s a um and so they just they wanted us under 1 roof and even though I said hey if this works out. Well we’ll likely move here. Um I had to change that pitch and so on the third conversation I said you know David’s moving to San Francisco we’re going to be working together. He’s in a move in like a month and ever it just that was never a yellow or red flag from anyone there on and then freestyle capital. Um, led the round but we had upside partnership Kent Goldman Semil Shaw from haystack and a lot other great angel investors come in and help lead that seed round which was ah two point one million

Alejandro Cremades: It’s amazing. So and then how did that they grow over time because I believe that you guys say prior to the transaction. You guys have raised a close to 70000000 correct

Courtney Guertin: Yeah, so how that kind of progressed was in 2016. There was this little snap of um saas not doing very well. It was very cold market and it was short lived but it was it was real for us. We felt that and one of our investors. That didn’t get ah a big of a bite so to speak they didn’t invest as much as they were hoping to there wasn’t room for that. They basically said hey we’ll lead in early a you might not be totally ready for it. But we’re there for you and that was metamorphic which is now compound and they. They helped forget that exact amount but that was roughly $2000000 and so that was an insider kind of thing to get us. It was. We didn’t need it as a bridge but it was just that grow and and add more to the people to the team then in um, then we raised I think the following year. Um, from propel ventures and we raised a proper a round and Ryan Gilbert and David Mort epiproelll ventures were were big believers in us and they had other companies like guideline you know it’s a 401 K Big company they done investments in like coinbase and so kind of the the new fintech or or insurer tech kind of play so that aligned really well with them. We then went on to um, kind of we went a little bit more of the pe route and and just to be but we just didn’t have. We had good numbers.

Courtney Guertin: But we didn’t have the numbers at like a benchmark or excel or we talked to them but they they wanted us to grow a little bit faster. We couldn’t at the time and so we we ended up for this is the first time for me, you know, being investing in only kind of traditional vc to kind of. See what? ah some more of the pe world would be and that was centenna growth Centtana Growth Partners a great team. There. They let our series be that was 19000000 and then um and then spectrum equity came in on series c for 41000000

Alejandro Cremades: Nice now talk to us about the recent cell because there was a recent transaction that that has happened here with these.

Courtney Guertin: Yeah, so if you would ask me a year ago would would we be sold and would we have sold to employee navigator I would have said no so these things happen out of nowhere sometimes and if you build a big business. I mean and you have treat your customers. Well you know good things can happen in this case it did. We had our biggest competitor employee navigator approach us. They’re really big on the East Coast they deal with companies a little bit bigger there and you know. Same business model. They go direct to they sell through the insurance broker they’re not calling employers directly like a lot of these gustos and if it namely companies do and so they’re very aligned and they’re also carrier in payroll agnostic meaning they’re not creating their own payroll company. They’re not. You know they they work with every insurance company. The goal is is to be a ah hub for um, the marketplace and choice of of brokers and in their employer clients and how the data gets entered so we’re kind of the system of record so to speak. For the employee benefits choices that these employees make and then we send everything electronically through Apis um, etc to these insurance carriers and so they were um.

Courtney Guertin: They had a little bit more employees we at the time had roughly three point five million employees that we managed employee benefits for roughly eighty five thousand employers and their average employers were a little bit larger so you know we ease was 43 employees on average There’s just over a hundred and so they similar kind of employee ye and customer account but they had a lot more employees on their platform. They owned again, kind of the East Coast side we did really well and we had a strong foothold on the west coast they said hey we have a lot of different customers. I’m sorry a lot of the same customers. Um, and I think it would be great if we kind of partnered together sort of compete together and we decided that that kind of made sense and we wanted to go through an loi process. Um, that loi. Kind of happened I guess December late December of last year and then we did ah the diligence was roughly just over three months and and we agreed to terms and so yeah, we did a merger acquisition and now ease is with employee navigator and we have 13000000 employees collectively. That are managed and I believe that we’ll be on the way to do pretty much half of all small media and businesses in the next few years in America representing close to 30000000 employees.

Alejandro Cremades: And I heard that it’s rumored to be close to a billion and the the the the resulting entity. So so really, really good stuff here.

Courtney Guertin: Yeah, it’s it’s a sizable company and we’ll continue to definitely be in the billions. Ah beyond.

Alejandro Cremades: So I guess a you know obviously to to get it to this point you know you you definitely have had you know the opportunity of dealing with people and really experiencing leadership at its best I mean.

Courtney Guertin: Ah.

Alejandro Cremades: What have you? What have you learned and what are your beliefs around leadership.

Courtney Guertin: Yeah I think the biggest one is I’m actually a big believer in do more with less and have constraints on yourself and team So it’s interesting. We made the most we we did the best.

Alejandro Cremades: Are.

Alejandro Cremades: Are.

Courtney Guertin: And persevered the most when we had I would say um more constraints on our capital. We made more mistakes when we had lots of capital you know, hiring too fast um and and and I think it’s.

Courtney Guertin: So less is more basically constraints can be a powerful motivator and I think you can you can really amplify your smaller teams to do more so that’s key keep teams small keep them motivated you know and um and have that kind of constraint. Another one is is really I found as you’re hiring and as you’re growing. We had to consistently repetition is key so keep your business model. Simple easy to explain keep your um. Your values of your company simple. You don’t need 10 of them. You know 3 is enough right? and repetition. What do you do? How do you service your customers. How do you care? repeat it always you got to be a broken record because you might say at once at an all hands meeting. And then if you don’t say it again for another couple months if you’re growing fast 10 % of the people have never heard you say it and so and you know fast forward than six months you know a third of your company has never heard you say this so you feel like you’re were saying these things once in a while. But you gotta constantly repeat. It. So keeping things simple constantly repeating um lead. By example, you know, ah really care do the work and show up. Um I made a couple mistakes of I thought I was delegating a lot. But.

Courtney Guertin: Kept on probably taking on too much personally so be really aware of you got to? you know you got to be in the trenches sometimes with your team but you also have to delegate and and consistently motivate. Um and and offer up. Ah, it’s the only way to expand. Your goal is to have your team be able to automate themselves out of a job or you know grow themselves out so that the company can grow including yourself like you don’t want to be needed in the weeds.

Alejandro Cremades: Um, now imagine if I was to bring you back in time you know maybe to that moment where you were still a dig and and thinking about starting something of your own. Imagine if you had the opportunity of giving that younger self one piece of advice before launching a business. What would that be and why given what you know now kerny.

Courtney Guertin: Um, I would say that um sometimes for example I wish I would have given a couple things a little bit. Don’t chase. The first thing always immediately. So I had a lot of different ideas on on the plate. And sometimes having a little bit of momentum just pulls you you have this inertia and you just go and so I had a 4 or 5 things that I was really excited about curiosity was great. I had the time to explore them and we got a seed. Ah.

Courtney Guertin: Basically a term sheet and and I was excited about the you know the rewards platform but there was other big things out there and curation space and Pinterest was coming on and that term sheet kind of just like. Pulled me and I had to give up all these other things without the proper research I know timing’s there and it was and it led to some some very wonderful friends. A great business and a lot of lessons learned but I feel like a lot of people chase. The first thing that they kind of see. And and um, you don’t want to delay forever. But if you get inertia behind something you might look back 5 years and been like why did I do that and it was just because you just got missionally down that path so just make sure that it’s something you really want to do for a decade. These things definitely take a decade or more to play out in any big way. Um I think taking venture capital is um, necessary at times but less so than most people think I think the biggest lesson that I learned on this is um, it. Really make sure that you think you need it. It’s needing for scale. It’s a certain type of thing. Um bootstrapping is is and or building a cash flowing business can can net out a lot more I would say liquidity.

Courtney Guertin: And and better results for for you personally um than doing the Vc game but it is it. It changed my life. Um I would say that.

Courtney Guertin: I Wish I would have been a little bit more cash restraint on the money. Sometimes you’re kind of told go higher hire Grow grow grow and um, you don’t always need to go do that you should You should do it in a I would say ah um I learned a lot of lessons from from over hiring. Um, but ah the at the end of the day that’s kind of what I would do is say hey to summarize it um term sheets. It will build inertia and and you make sure that you’re really excited about it for the 10 year Journey I had.

Alejandro Cremades: Missing so Knie for the people that are listening that will have to reach out and say hi. What is the best way for them to do so.

Courtney Guertin: Yeah, so um, courtstar c o u r t s t a r r on Twitter at quastar and then I have a fund. Let’s go fund and you’ll find some of the investments that I’ve done and some more contact information there please reach out i. You know I’m going to continue to build buy and invest in businesses and I’m excited to connect with everyone in your excellent audience that you have so. Thank you.

Alejandro Cremades: Amazing knie! Thank you so much. And yeah, again, you know anyone that is listening you know feel free. You know now you know man but anyhow Kerny thank you so much for being on the dealmaker show today. It has been an honor to have you with us. Thank you.

Courtney Guertin: I Appreciate your time. Thank you so much for having me.

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