Latest / Beyond Fulfillment Podcast / Solo to CEO: Scaling from Coffee Shops to a $20 Million Dollar Agency with Jason Hennessey

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Solo to CEO: Scaling from Coffee Shops to a $20 Million Dollar Agency with Jason Hennessey · Beyond Fulfillment Podcast

• 0:00
  Foreign.
• 0:05
  That's the secret to success.
• 0:07
  I mean, it really is when you can get to the point where you can buy back your time.
• 0:13
  You know, I know Dan Martel wrote a book called buy back your time, right?
• 0:17
  But, you know, truly, like, when you get to the point where you can actually start reinvesting some of the profits into people and, you know, hiring people that are way better than you at a specific task, like, I
• 0:29
  mean, that's the power of being an entrepreneur.
• 0:34
  Today's guest is Jason Hennessey, a true trailblazer in the world of digital marketing and SEO.
• 0:42
  Jason is the founder and former CEO of Hennessy Digital, an agency that he scaled from scratch into a $20 million enterprise before its recent acquisition by private equity.
• 0:55
  From his early days as a mobile DJ in Las Vegas to self teaching SEO to grow his business, Jason's journey is all about relentless curiosity, unconventional thinking, and building companies that make a real impact.
• 1:09
  In this episode, Jason shares lessons from bootstrapping two agencies, how he leveraged remote work to recruit world class talent, and the mindset shifts that it took to delegate, scale and eventually sell his company.
• 1:24
  He shares real world, real world advice on hiring, overcoming early mistakes, and what excites him about the next chapter post acquisition.
• 1:33
  If you want actionable insights from an entrepreneur who's been there and done it, this episode is for you.
• 1:40
  As always, if you found value from this content, please like and subscribe.
• 1:46
  All right, Jason Hennessey, welcome to Beyond Fulfillment.
• 1:50
  Thanks, Dave.
• 1:50
  I appreciate you having me on here today.
• 1:52
  Yes, sir.
• 1:53
  We appreciate you taking the time.
• 1:56
  So, Jason, you are the founder, the CEO of Hennessy Digital, which is a digital marketing firm that you've had for 10 plus years, which you recently just sold.
• 2:08
  And we will get into that.
• 2:10
  But you had a very unique start to your entrepreneurial journey and how you got into the field of digital marketing.
• 2:18
  Just for the audience, can you tell us how that all happened?
• 2:21
  Sure, yeah.
• 2:22
  For the sake of time, I'll kind of give the the cliff notes of the story.
• 2:26
  But I got out of the Air Force.
• 2:29
  I, I joined the Air Force to pay for college.
• 2:32
  Once I got out of the Air Force, I was a mobile DJ.
• 2:36
  I was DJing weddings and parties while I was kind of going to college.
• 2:40
  And so this is back in 2001 and I needed a way to kind of drive new potential brides that were getting married in Las Vegas where I was living, you know, to learn more about my D.
• 2:53
  And so I stumbled upon this thing called SEO and I taught myself it.
• 2:59
  I became an autodidact I guess, if you will.
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  And now, you know, two decades later, you know, I'm still practicing SEO.
• 3:07
  It went from a need to a passion to an obsession.
• 3:12
  And so now I kind of have written a couple books on it, I've built and sold a couple agencies and, and I'm excited for the next chapter, I guess here.
• 3:24
  Okay.
• 3:24
  Well, yeah, a lot to get to unpack there.
• 3:27
  So you, I mean, talk about great timing.
• 3:30
  So you were just, just starting your entrepreneurial journey, looking for a way to grow your business as the Internet was really just taking off and becoming, you know, mainstream.
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  So at that time, I mean, did, did you have a sense of how, how big and how important the Internet was going to be for, for business growth?
• 3:52
  I did, you know, because I was going to college, I was studying business and marketing and there was a, a service.
• 4:00
  It was kind of the genesis of PPC as we know it.
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  It was called Overture.
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  And so this is where you can actually bid for keywords back back in the day.
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  And so once I seen that that was a possibility and I just knew like, this is going to be the future as we know it.
• 4:20
  And so I kind of went all in and I just started to kind of teach myself and I just kind of obsessed over, over it, started to get good, started to tinker with websites.
• 4:31
  You know, as you probably know, like, the Google algorithm is not something that you can just buy a book upon and just read it.
• 4:37
  It's, you know, it's kind of like being a doctor.
• 4:40
  You have to like practice and test things out and see if it works and then just kind of leverage it.
• 4:45
  And so, yeah, that was kind of the journey.
• 4:47
  But yeah, back in college I kind of knew that this was going to be the future here, so.
• 4:53
  Okay.
• 4:54
  And I read in your bio also that you were a self described hopelessly distracted C student.
• 5:02
  Yeah.
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  And so when you came across this and you knew that this was, you know, really going to be big, but yet there, you know, it's just starting out.
• 5:13
  There's not like a lot of literature and people don't really have this whole thing figured out.
• 5:18
  I mean, how did you go about the process of just like teaching yourself SEO as that whole industry is just starting to come into shape?
• 5:28
  Yeah.
• 5:28
  So back then it was, and you know, it was more of the wild, wild west, I guess, if you will.
• 5:33
  Right.
• 5:33
  So there wasn't as many tools as we have access to now now.
• 5:36
  There wasn't that many books that was written on the topic.
• 5:41
  You know, half the battle was finding out who you can trust in terms of the, what you're reading.
• 5:47
  Right.
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  And so I, I studied a guy by the name of Aaron Wall.
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  He had wrote a book called SEO book.
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  He had the domain seobook.com and so he had this really thick book.
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  And so I read it from, you know, front to back twice.
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  And then I just started to practice, you know, what it was that I was reading and doing a lot of experimentation.
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  And then from there, you know, I started to get some early results.
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  It wasn't as competitive as it is now, and the strategies have kind of changed, you know, over the years.
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  But as far as the baseline core principles of how the Google algorithm works, I mean, it's for the most part, you know, similar.
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  And so just iterations and then hiring people and delegation, and then over the years, just kind of built up an agency to do it for others.
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  What, what I've been practicing for so many years.
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  Okay, all right.
• 6:42
  So you, you realize this is going to be something big.
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  You, you, you latch on to, like this, this SEO book, which seems to be like the best authority you can find.
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  You read it front to back twice, and you start implementing and getting some early results.
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  So from there, what of, of kind of scaling that company and where you went next?
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  Yeah, so that was mostly tinkering for my own DJ company to try to get more people to hire me to DJ their parties and weddings.
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  Then, because I've got pretty good at this SEO, I built up a wedding directory.
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  And this is where brides can come plan their weddings online in Las Vegas.
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  It was called Vegas Wedding Mall.
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  Then I built Seattle Wedding Mall and Los Angeles Wedding Mall and all these other wedding websites, built that up.
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  Ended up selling that.
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  Moved to Atlanta, Georgia with my family from Vegas.
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  And then I found the world of legal marketing.
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  I got asked to speak to a group of lawyers.
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  During my presentation, I had about seven lawyers come up to me and ask me if this was something that I did for law firms.
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  And it wasn't.
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  But I took their business cards.
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  And so that was the genesis of me entering in to the world of agency life.
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  Built up an agency, it was called Everspark Interactive for about eight years.
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  I then sold that to my business partner, moved out west to California, which took me on my new journey of opening my own agency called Hennessy Digital.
• 8:21
  And so that was in 2015, and I just recently sold that to a private equity group, but I am still the CEO and I'm on the board of the parent company called Herringbone Digital.
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  And I'm a large shareholder now of that as well.
• 8:38
  Okay, all right, so.
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  So you realize the, the power of the, the agency model and clearly you.
• 8:48
  Were good at it.
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  You had some success.
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  So once you, you sold the company back to your partner and you moved out west, did you know, right, I can do this, I'm good at it.
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  I just want to do it for myself.
• 9:01
  Now was it, was it pretty much like decided upon that's what you're going to do?
• 9:05
  Yeah, I think when you have business partners, you know, you have different appetite for growth and risk and all that other things that comes along with being an entrepreneur.
• 9:15
  And so at the time, you know, it just kind of made sense.
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  You know, we were, you know, had two different visions, I guess, of kind of where to take the company.
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  And so I ended up selling it to my business partner.
• 9:30
  He continued that journey and that's still a company that's in existence today.
• 9:35
  I took a sabbatical leave.
• 9:37
  I took about seven or eight months off, played a lot of tennis, you know, just kind of spent time with the family.
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  And then I just knew that I was, you know, probably in a good position to start over and so didn't have any partners.
• 9:53
  It would have been just my vision.
• 9:55
  And so I built it up from ground zero again and then took it to north of 20 million before I then exited again in about 10 years from the date that I started it.
• 10:09
  Okay, so that's sabbatical too, right?
• 10:13
  Like having that downtime to just really get out of the daily grind and just relax and not have deadlines and like you said, spend time with your family, play tennis, you know, do whatever other activities.
• 10:25
  How important was that to really shaping your vision for the future and really getting that clarity on what you wanted to do next?
• 10:34
  I think for me it was, it was great just because we just moved to a brand new city.
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  We didn't know much about Los Angeles at the times.
• 10:43
  My son was getting into the acting space, so like my wife and him, my wife and myself were kind of supporting his young acting career.
• 10:53
  We'd be driving him to like Sony Studios or, you know, Paramount, you know, for auditions and stuff.
• 10:59
  And so it's kind of like living a big vacation, I guess, if you will, for, you know, many months.
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  And so that was really cool.
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  But then there came a point where my wife was like, you know, you're gonna get back to work here, like.
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  And so, you know, and you know, as an entrepreneur, you know, you're always like ready.
• 11:18
  You need something to kind of take that creative Energy, Energy.
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  And, and, and, and so, you know, I built up my agency.
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  Believe it or not, my son was doing acting classes and there was this little coffee shop in the middle of Toluca Lake, which is in California.
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  And I would basically just kind of be building the agency, right.
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  From a laptop, from the coffee shop as we waited for, you know, him to kind of get out of acting classes.
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  And then from there, you know, you just kind of grow, you start delegating, you start hiring people.
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  And you know, and then it's that whole snowball effect where it just kind of continues to get bigger and bigger and bigger and, and you know, I surrounded myself with the right people, I got the right coaches.
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  I learned from all the mistakes that I made with my first agency.
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  So I had like, shortcuts on, you know, what to do, what not to do.
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  And, and it's just been a, an exciting journey and I'm, and I'm ready for this next chapter of life, you know, having a company now that's backed by private equity.
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  So.
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  Okay.
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  All right.
• 12:24
  And appreciate you bringing that up too, is kind of learning from your mistakes.
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  I mean, what.
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  Can you just give us some insight too on some of the mistake, the early mistakes you made and what that taught you and, and as far as for building for the future.
• 12:38
  Yeah.
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  So I think the first, I don't know if we call it a mistake, but it was just a lesson for me.
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  So when we built my first agency, we found this beautiful office.
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  We were like on the 28th floor.
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  It was in the middle of like Sandy Springs, which is just outside of Atlant.
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  And so we furnished it.
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  We had to hire from a 5 or 10 mile radius of this building.
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  Right.
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  You know, and if you really want to get world class talent, you shouldn't, you know, make it so that you have to hire from this radius of this building.
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  And so when I launched my new agency, you know, it was designed to be a remote company.
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  Right.
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  So if I wanted to recruit world class talent regardless of where they lived, that was kind of by design.
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  Right.
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  And so, you know, that was instrumental in, to me building my new agency was not having a lot of overhead with, you know, leases and furniture and all this other stuff.
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  I was able to kind of put that, those resources towards talent.
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  And so I think that was a good lesson that I learned from my first agency to my second agency.
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  Okay.
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  All right.
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  And as you're building Hennessy Digital, I mean, what, what was the process like scaling?
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  Because now this is the, you're on Your own.
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  You don't have a partner.
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  So it's your vision.
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  You know, like you said, you went with a remote model.
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  You were doing it oftentimes from a coffee shop, on your laptop type of thing.
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  But what, what was the, the process and the growth trajectory like?
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  I mean, did things start to, like, take off right away?
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  I'd say the first three years of the business was more of like a lifestyle business.
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  You know, that's where I was kind of doing everything.
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  I was managing the sales process, I was managing the clients, I was doing payroll.
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  Right.
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  You know, I was kind of doing everything.
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  And I think that's typically how most stories begin.
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  You know, as entrepreneurs, right, you kind of find yourself taking care of everything.
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  And you're not world class at any one of those things.
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  You're just kind of doing it because it's a need.
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  But then it gets to a point where you start making money and you start to realize, like, hey, there's things that give me energy and there's things that take energy away, right?
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  And so how do I start to delegate the things that, like, don't give me energy that I'm not good at, like accounting and, you know, and other, you know, parts of the business?
• 15:17
  And so from there, you just start to delegate those tasks to people that are way better at that than you are.
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  And, you know, you're going to make mistakes, you know, at those points.
• 15:29
  I think the reason why most businesses fail is because they start delegating those tasks to people that they can afford, not necessarily the best person for that role.
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  And so, you know, we've made some mistakes.
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  You know, we got past them, we learned from them.
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  And then eventually you start hiring and recruiting the right people.
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  You start putting, you know, some leadership in place.
• 15:55
  You start getting better practices in terms of how to hire the right people, the questions to ask.
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  Right.
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  And then from there, you know, then eventually you.
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  You get to the point where you start to delegate almost everything that you do so that you can just focus on whatever it is that, you know, you feel is your zone of genius.
• 16:14
  And for me, that was sales initially, and then I was able to finally delegate that out people.
• 16:20
  And then that was just more of me just kind of building out the personal brand, speaking on stages, writing books, doing podcast, the stuff that drives most of our leads today.
• 16:32
  You know, I've been laser focused on that kind of stuff.
• 16:36
  Okay, all right.
• 16:37
  And, you know, couple great points there.
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  But so many entrepreneurs, too, get caught in that trap of just kind of doing everything and not wanting to delegate feeling, feeling like they can't give up control of this task or this department or whatever.
• 16:58
  And then you bring up such a great point in terms of hiring what you can afford versus the best person for the job.
• 17:06
  So like for entrepreneurs that are listening, right, so maybe they're stuck in that cycle right now and they, they say, look, Jason, I hear you, but how am I supposed to hire who I can't afford if it's the
• 17:19
  best?
• 17:19
  Like, what are some practical ways that that other entreprene can kind of transition out of that trap?
• 17:26
  Yeah, I think sales is really kind of what drives solutions for that stuff.
• 17:32
  Right.
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  Because revenue will help fix a lot of problems.
• 17:35
  And so you just kind of have to wither through, you know, that, that very tough period where, you know, maybe you bring in somebody that's just right out of college to help with account management or something.
• 17:51
  Right.
• 17:52
  And so you're gonna have to spend a lot of time training them and micromanaging them, right.
• 17:59
  And hopefully get to a point where they feel self sufficient and they can.
• 18:02
  Just say like, I've got it right.
• 18:05
  There's about a good 50, 50 chance that they do and there's a 50, 50 chance that they don't.
• 18:09
  Right.
• 18:09
  And so it's a pain in the butt when you spend three months training somebody and then they're just not the right fit or they leave to go somewhere else for more money.
• 18:18
  Right.
• 18:18
  You know, I mean, that's a real risk when you're people like that, right.
• 18:23
  And so, you know, as you're kind of navigating the waters, eventually you're bringing in more business, you know, because now they've got like that somewhat under control, that task.
• 18:35
  And then from there, you know, as you have more revenue coming in, then you could maybe start to afford people that are more competent in those specific roles.
• 18:45
  You learn from the lessons.
• 18:47
  Hopefully you've built systems and processes along the way, you've adapted, you've made changes.
• 18:52
  Right.
• 18:54
  And, and at that point you're just a very agile company.
• 18:57
  Right.
• 18:57
  You can make changes very quickly.
• 19:00
  And you know, once you start getting to the point where you have like a hundred people, 150 people, you're not as agile anymore, Right.
• 19:07
  Because you can't just change systems and processes on the fly every single day because it impacts so many people in so many roles.
• 19:15
  But early on you can make a lot of changes and you can make a lot of mistakes.
• 19:21
  Okay.
• 19:22
  And how going from lifestyle business that you start in a coffee shop and having that flexibility and that Agility.
• 19:31
  Early on, how did you manage the transition as the company grew and scaled and like you said, you had over, I think it was, what, about 150 employees at one time?
• 19:41
  Yeah, yeah.
• 19:43
  It really comes down to finding somebody that could be like your second in command, you know, finding a good, competent COO to kind of take the business operations side off of you so that you can focus on whatever
• 20:04
  it is that you're best at.
• 20:05
  Like I said, for me it was sales, and then eventually it became more of just building the personal brand.
• 20:11
  But I would say, you know, you get to a point where when you want to transition from a lifestyle business to a.
• 20:18
  Like a business that you're looking to scale and at some point selling, you need to bring in really competent people.
• 20:24
  And so, you know, in my case, it was uncomfortable, right, Because I was bringing in people that were super qualified at specific roles, like a COO and a cfo.
• 20:36
  And these are people that, you know, are not cheap, and they've already brought other companies to exit before, and so they already know what it takes.
• 20:48
  And so if you want to get that level of experience, you have to pay for that level of experience.
• 20:52
  And so that was a move that I made, you know, probably about four years into my journey, and that set us up for really scaling the business much more efficient and effective.
• 21:07
  Okay.
• 21:08
  And as you started to transition, I guess like your.
• 21:12
  Your original zone of genius with sales for a long time, and like you highlighted, that's so important to a growing company.
• 21:21
  Like, how did you find out that after you could delegate that, that your next step was the, you know, the writing the books and the speaking on stages and that sort of thing.
• 21:31
  Yeah.
• 21:31
  So just one of those things that I quickly realized that, you know, if.
• 21:35
  If I wanted to take a vacation, if I wanted to go, take two weeks off, you know, to take my family to Florida or go overseas or whatever, you know, I knew that the business stopped growing when I
• 21:46
  was away.
• 21:47
  Right.
• 21:48
  And you really can't scale a business when it's so dependent on one person.
• 21:55
  And if they leave, you know, the business just kind of just stay stagnant for that period.
• 22:03
  So I eventually brought in people, two guys that I trained to be salespeople, one of which didn't have any experience in SEO at all.
• 22:17
  He actually sold timeshares.
• 22:18
  He was a longtime friend, and the timing was impeccable.
• 22:22
  He was looking for a new opportunity, so brought him in, trained him on it.
• 22:26
  He became really passionate about it.
• 22:28
  He started learning about SEO on his own free time.
• 22:31
  And Then I brought another gentleman in by the name of Rob, who was a former client of mine that was the one managing the agency.
• 22:39
  And so he saw it from that.
• 22:41
  That side, and so he had a quicker way of kind of adapting and learning.
• 22:47
  And then from there, I just kind of set it up where they shadowed me on calls, and I shadowed them on calls.
• 22:52
  And then we got to the point where they were comfortable in taking some of their own calls.
• 22:56
  And then from there, they just had it.
• 22:58
  And then I could go away for, like, a month, and the business would continue to grow without me.
• 23:04
  And then that allowed me to kind of have more time where I could focus on making videos and posting on LinkedIn and, you know, building out my personal brand, writing books, things like that.
• 23:17
  And nowadays I still do a lot of that, but then I also will fly in and I'll look at what is the biggest constraint in the company right now and how can I fix that.
• 23:28
  And that's really where I spend most of my time these days.
• 23:31
  Okay, and how liberating was that?
• 23:34
  Going from kind of scrappy entrepreneur to always being responsible for the sales to finally being able to hire, like, competent help that could generate that and then allow you to really, truly work on the business instead of just
• 23:47
  working in the business.
• 23:49
  That's the secret to success.
• 23:51
  I mean, it really is when you can get to the point where you can buy back your time.
• 23:57
  You know, I know Dan Martell wrote a book called buy back your time, right.
• 24:01
  But, you know, truly, like, when you get to the point where you can actually start reinvesting some of the profits into people and, you know, hiring people that are way better than you at a specific task.
• 24:12
  Like, I mean, that's the.
• 24:14
  The power of being an entrepreneur, you know, because then it gives you flexibility to take longer vacations, travel the world, or just do what it is that you want to do, you know, at the company.
• 24:30
  Okay.
• 24:31
  All right.
• 24:31
  And as you mentioned, right, you just recently sold to.
• 24:35
  To a private equity firm, and you're still the CEO and a large shareholder, but.
• 24:41
  And you mentioned several times you're excited, excited for this next chapter.
• 24:45
  So what.
• 24:46
  What does the.
• 24:47
  The future have in store for.
• 24:48
  For Jason Hennessey?
• 24:50
  Yeah, so it's really powerful because I've always built this business with kind of like a bootstrap mentality and budget.
• 24:58
  And so you have to operate lean and mean and very, you know, efficient, trying to do more with less.
• 25:06
  You know, when you bring in private equity, it, like, allows you to accelerate growth faster, gives you access to Capital that could maybe bring more ideas to life quicker and then also growing by way of acquisition.
• 25:23
  Right.
• 25:23
  So if, if we see that there's somebody that could be a very strategic partner to what it is that we're trying to build, rather than build it ourselves, sometimes it's easier just to go out and try to acquire
• 25:37
  other companies.
• 25:39
  And so that's what I really love about what I'm doing now is not so much just continuing to grow my agency and providing world class services to our clients, but also strategically aligning with other companies and agencies that
• 25:58
  could help get us to the next level faster by way of acquisitions, too.
• 26:04
  Okay.
• 26:05
  All right.
• 26:06
  And Jason, if people want to reach out to you, learn more about what you're doing and potentially how they might be able to work with you or for any other, any other reason, what's the best way that people
• 26:17
  can, can reach out to you online?
• 26:19
  Yeah, so best I think is, you know, maybe connect with me on LinkedIn.
• 26:24
  I'm pretty active there.
• 26:25
  I post content all the time.
• 26:27
  I love keeping up with other entrepreneurs as well.
• 26:31
  So once we're connected, you know, I can follow your journeys, you can follow Min, and you know, if there's any questions that you guys have, be sure to send me a dm.
• 26:40
  Okay.
• 26:41
  And we'll link that in the show.
• 26:42
  Notes for everyone.
• 26:44
  All right.
• 26:44
  Well, Jason, thank you so much for taking the time to be here and sharing all this valuable wisdom from your journey with our audience.
• 26:50
  We greatly appreciate it.
• 26:51
  Thanks for having me, Dave.
• 26:52
  I appreciate it as well.