As a business owner, it’s difficult to do the right work AND guide your company toward its next big initiative.
With Red Direction Business Base Camp, learn how to implement and handle processes to meet your business’s specific needs and better understand your market.
Starting the conversation:
How do you innovate and take chances with mouths to feed and mortgages due? Forget the theory — practical risk in action is bold, pragmatic, and profitable — Rich Kahn, CEO and Co-Founder at Anura Solutions, LLC, shares real-world experience in the art of controlled risk.
Constraints are a part of life, and embracing them changes the view while elevating ideal solutions (not all of the “workable” solutions). You can achieve your biggest dreams even when taking risks that ensure stability. Pragmatic risk-taking isn’t sexy, yet it does offer BIG results over time.
In this episode, you will hear the reality of situational decision-making, how to know the beat of your business when you aren’t there, and how to evaluate the way you think about constraints so that you find the best decision for your next step. Jess Dewell talks with Rich Kahn, CEO & Co-Founder at Anura Solutions, LLC, about being BOLD and knowing exactly what you want to do to achieve your goals.
Host: Jess Dewell
Guest: Rich Kahn
What You Will Hear:
Rich Kahn recounts nearly selling a business for $60 million before the dot-com bubble burst, and how that changed his outlook and actions.
- He had a business ready to sell for a large sum, but the deal disappeared overnight as the tech bubble collapsed.
- Rich continued building his business out of necessity, shifting from potential windfall to survival mode.
- The experience shaped his view on risk, opportunity, and how financial constraints impact entrepreneurial decision-making.
How to balance risk as an entrepreneur who must meet practical responsibilities.
- Rich contrasts the big risks taken by those with fewer responsibilities to his own need for calculated moves due to family and financial obligations.
- Have a pragmatic backup plan.
- Perceiving and managing constraints drive different approaches to risk and opportunity.
Put everything on the line for the business and fully commit to its success alongside his partner.
- He and his wife decided to invest all they had into the company after agreeing that they believed in the product.
- The pressure and risk, realizing they could “lose everything” but chose to act boldly regardless.
- Have an ALL-IN mentality to propel business growth.
Plan for taking an extended absence from work, relying on his team and management structure.
- Choose a system to run leadership meetings and track progress while away.
- Taking an absence will test both his need for control and the resilience of his team.
- Choose how to re-engage with leadership meetings remotely, though he prefers in-person connections.
Be open and discuss your hopes (and fears) for the company’s performance while away.
- Ideally, the company continues growing, goals are accomplished, and operations remain smooth without his daily involvement.
- He’s preparing to step further away out of “physical demand,” reaching a new personal milestone in leadership.
- The worst-case scenario, for him, would be stagnation or decline, but he expects positive outcomes due to systems in place.
The surprising lessons in resilience from being able to remain calm when a massive business deal falls through.
- Rich Kahn’s unexpected calmness after losing the deal showed his confidence in ongoing business momentum.
- Strong financials and business direction helped buffer the disappointment and illuminate next steps.
- Hindsight: acceptance of setbacks shaped future success and adaptability.
How you define success, like achieving financial freedom, so that you can work for fulfillment rather than just covering expenses.
- Growing up poor fueled an ongoing drive to ensure his family’s financial security.
- Achieving a position where money is not the main worry allows for more creative and fulfilling work.
- Removing the pressure to “pay the bills” opens possibilities for fun and innovative entrepreneurship.
It is BOLD to know exactly what you are willing to do to achieve your goals.
Resources
Transcript
Jess Dewell
So talk to me about what’s been on your heart lately. Literally. Oh gosh, pun intended.
But we don’t have to, and by the way, if we’re still in this preview, I will switch to something and you’ll be like, I think we started and you’re right. I was just thinking, but yeah, what’s on your heart? Beside your heart.
Yeah.
Rich Kahn
Um, we’ve got three new sales people. This is the interesting thing. So I get a vacation.
This is a vacation. I go with a bunch of friends. Um, once a year we go to Dominican Republic.
We have a blast because we do nothing and it’s a vacation, right? It’s true vacation. We eat, we drink, and we talk about where we’re going to eat and drink.
That’s it.
Jess Dewell
Beautiful. We don’t get enough of those, I don’t think.
Rich Kahn
And the background is Dominican Republic, so you can’t go wrong, right?
Jess Dewell
Right, right.
Rich Kahn
But as soon as I get back, I get back on Saturday, Sunday, I’ve got three new members, uh, all driving in for training. Cause I’m going to be training Monday and Tuesday before I go into, uh, surgery on Wednesday. So I’m trying to do as much as I can.
Cause I am a control freak. Right. And for me to be out, like my wife’s not gonna let me have my phone for like a couple of weeks, which we’re going to have a, we’re going to have a, we’re going to have a fight.
You know, we haven’t had fights in a while. We’re going to have a fight. I need to see my phone.
Jess Dewell
So you’re a bad patient.
Rich Kahn
Oh, I’m a horrible patient.
Jess Dewell
I’m a horrible sick person. People don’t, I’m like, you gotta be around me. You gotta hold my hand and I’m going to bite your head off the whole time.
Rich Kahn
Well, this is, this is funny. Talk about being sick. Uh, for as long as I can remember, I tell everybody cause that’s true.
I don’t get sick.
Jess Dewell
Yeah.
Rich Kahn
Now when I, when I get sick, I talk about like bronchitis or flu or stuff like that. And, but I get other things like aneurysms, high blood pressure, you know, overweight, like, you know, more serious things, but like, you know, I don’t get the sniffles and the sneezes. I don’t get into that.
Jess Dewell
Yeah. Yeah. Just regular body change stuff from environment and wear and all things.
Yeah. Okay. Well, okay.
So this is actually now I know where we want to start, which is you have been an entrepreneur. How many businesses have you been had as an entrepreneur sequentially? Right.
Like just total 32 years. Right. Am I got, do I have that right?
Rich Kahn
32 years in the digital marketing space.
Jess Dewell
What about before that?
Rich Kahn
I did other businesses. Like I had, like when I was 11, I had my own landscaping business. Um, I was a paper boy, which is kind of entrepreneurial ish.
Cause you got to agree with that.
Jess Dewell
Well, that was back in the day where you actually had to knock on people’s doors and collect money. That’s entrepreneurship. Let’s just be real.
Rich Kahn
I’ve done that. I’ve done, um, let’s see. I’ve done a couple of small things, but nothing big.
I think my first real entrepreneurial business was an email marketing magazine, um, that I started in 93 before the internet went digital. And before, before you really had a browser.
Jess Dewell
Yeah.
Rich Kahn
So it’s only the geeks got online because it was very technical on how to get from one place to another. It was no easy way to get, it was interconnected. And I love that because in the eighties, when I was in high school, I built what was called a bulletin board system back in the day, which is today’s website.
And in order to access it, since computers weren’t always connected, you had to dial a phone modem into another computer to access that site. Uh, so I had, I had that all going that was actually connected to ARPANET, which was the predecessor to the internet. Yeah.
Jess Dewell
Yeah. I you’re saying all words. I know I never did that, but you’re saying all the words I understand.
I had a bulletin board as the internet was emerging. Uh, and at the end of high school and the beginning of college. Yeah.
So that’s so C okay. So email marketing before the internet is pretty interesting. So one of the things that I know that you’ve seen, then you, you have seen like the evolution and revolution of what technology can do for companies in a way that most people haven’t, even if they’ve been in business that long, whether it’s corporate or otherwise staying in the space that you have stayed in really get, it feels like it would give you some sort of an edge.
Do you feel like you have this? Um, do you feel like you have a deep business instinct about it? Like, you know, what’s going to be coming before it comes?
Rich Kahn
Absolutely not.
Jess Dewell
Okay.
Rich Kahn
Well, because if I did, right, I’d be retired by now.
Jess Dewell
Well, um, well, come on. Would you really, you’d be finding something to do. I don’t think you’re a, I don’t think somebody who’s going to retire in the traditional sense.
Let’s just be real.
Rich Kahn
No, I’ve got a thousand things in my mind that I would do, but like, no, seriously, if, if I knew it was coming, like if I knew social media was coming, I would have started a social media site. Right. If I knew, you know, AI was going to be hitting it, I would have been like, and actually not for nothing.
My first in, when I was going to college, I got accepted to MIT for, it wasn’t called robotics engineering. It was called electromechanical engineering. And I really wanted to study AI, making robots more human, but 30 something years ago, when I, when I was getting, you know, going to college, it was technology was nowhere near where it is today.
Like today, right now, being a robotics engineer would be awesome because you have the AI available. You have access to very inexpensive components. You know, a lot of that work that’s been done over the last 30, now’s the time that I would, I would have enjoyed.
And you know what? If I ever decide to retire from this business, I might, one of the things I said I would do is go back to school for robotics engineering, just for fun.
Jess Dewell
Love that. So you, you haven’t achieved all your dreams. You are not what you want to be when you grow up.
Rich Kahn
I’m still trying to figure out what I want to be when I grow up.
Jess Dewell
Me too. I love that. And that makes, that makes life fun and different.
How does, how does that desire to do robotics and knowing that someday you’re going to go back to school and do something totally different than you’ve been doing? How does that, how do you think that influences your thinking today?
Rich Kahn
So here’s, here’s, all right, we’ll get a little bit into this.
Jess Dewell
Yeah.
Rich Kahn
The thinking for me, my whole life, every business I built was bootstrapped. So you asked me a question, how many businesses I built? I think I built six or seven.
I have to count them up. All bootstrapped and all having to pay bills. So I didn’t have the flexibility of like, if you’ve ever seen the social network movie on, on Facebook and he, and he says, you know what, we’re just going to build something cool because he didn’t have to, he didn’t have bills to pay.
Right. He was in school, he was just having fun. And that to me is how some of the best businesses are built is let’s see if we can do this.
The ones that are built, you know, you build strong businesses, but it’s like, you know what? I want to build this business because I have rent to pay. I have a mortgage to pay.
I have kids to raise. You know, you make different decisions like that. So I’m kind of interested, like I said, eventually when I, you know, eventually when I retire from this business I hopefully won’t have to worry about, you know, paying the bills anymore.
And now I can go do the stuff just for fun.
Jess Dewell
You know, that’s okay. So can you, I would like to give, now I’m going to ask this question because I’m very curious. You know that you would make decisions differently if your situation was different.
Did I, did I reflect? Okay. So can you give me an example of a decision that you would make today using the constraints with what you’ve got and then what that could look like if and when you don’t have those same constraints?
Rich Kahn
All right. So I had a business and I may still build this business idea out so I won’t get into the details of it, but I had a business that was really cool. And in three months I had a buyer looking to buy the business from me for $60 million.
It was a couple of partners in the business. This was 2000. Oh, hello.
Jess Dewell
Good place to be. Technology business. Yeah.
Yeah.
Rich Kahn
Well it was for a period of time. We had it all locked up.
Jess Dewell
2000 it was still good. That’s not good.
Rich Kahn
Well, April 28th it was not good.
Jess Dewell
That’s true.
Rich Kahn
So I’m guessing it was before, right?
Jess Dewell
Yeah.
Rich Kahn
So we had the company sold and it was getting infused with money and we were going to be able to take this to a very different level. And at that point, because we had an influx of cash, I was not worried about money anymore. Like worried about paying the bills because I knew, okay, we’re getting in 60 million.
My bills are going to be covered. Now I can just go do things for fun. And I had a very, really interesting business built out that even today would be a phenomenal business.
That’s why I said I may eventually build that business out so I won’t get into too many details. But I actually have several ideas just like that. But just the thought of it now, it didn’t get sold because of the fact that it was supposed to close April 28th of 2020.
And April 14th is when the .com bubble burst right before tax day. So the deal came off the table and I just continued building the business because I had to pay the bills. However, I had a glimpse of some of the ideas I was coming up with and some of the coolness that would have been around if I could have done that.
And I think you would get, when you’re not worried about paying the bills, you worry about making things more fun, more enjoyable. And because you’re not playing it safe anymore. You’re being ballsy because you can.
If it fails, it fails. Who cares? You go out and do something just for fun.
And I think if you look back over the last 30 years, the internet’s been around. The internet’s been around since September 1st of 1991. That’s when it got turned off.
From all everything I can look up, that’s the date that it went live to the public. If you look at all the businesses built, some of the ones that are like really cool today are ones that were, let’s see if we can do it. Google.
They weren’t paying bills. Yahoo. Now granted, Yahoo isn’t what it was 20 years ago.
Jess Dewell
But I think it’s good to call them in. They go in that category for sure.
Rich Kahn
Yeah, they go in that category. There was two guys out of a trailer park that decided to put this, the internet was taken off and they decided let’s make an index. Like, you walk into a mall and you see a directory, let’s build a directory.
No one knows where to go. No one knows how to get there. Let’s show them the way.
They were just trying to put something together that was different and cool. And a lot of the businesses that are household names today were just, that’s how they started. They weren’t, let’s build a business because I got to pay bills.
That wasn’t, they had a different mentality, a different mindset. And I think that’s what made some of these businesses that we all live in. TikTok was, I’m sure it was, I don’t know the story of TikTok, but I’m sure it had to be with, let’s do something different in social media.
Jess Dewell
I think, so there’s a couple of things that are bubbling up for me. One is, could it be, is it the actual constraint or is it our perception of the strength that, or the constraint that makes us approach our decision-making?
Rich Kahn
Perception. I think it’s a hundred percent perception because you can still do the same thing, but you do it with guardrails on. Like, okay, I can’t invest, I can’t, I can’t walk into a casino and bet black and hope I win because I got a mortgage to pay.
I got kids to feed. I got, I’ve got responsibilities. So let me spread it around the board a little bit.
Let’s play it a little safe. Okay. We’re not going to hit a home run, but you know, if this hits, I’m going to, I’m going to make profit.
If it doesn’t, I’m still going to be able to pay the bill. Like at least maybe, maybe I’m the only one who thinks like this. I doubt it.
But when you’re building a business and you have concerns to worry, that’s why some of the best, some of the best businesses start as side hustles, right? Because the bills are paid. Let’s go do something for fun.
And if it fails, it fails. No, no big deal. It’s fun.
Right? And if it fails, we had fun doing it. If it succeeds, that’s kind of the direction.
And that’s just how I, maybe my experience is a little, I’m sure it’s different than everybody else, but I’m sure people had similar, similar space where you just, you just think differently. You make different decisions. Like my father always calls me a risk taker.
And I say, no, I’m not. I’m more of a very calculated risk taker because I’ve always had bills to pay. I’ve always had to worry about how I’m going to feed the family.
Jess Dewell
So when you talk about what, now I’m curious, because I agree with you about the perception piece. It’s all about the perception of our constraints and where the rubber meets the road and what our priorities are as people, household, the obligations we have accepted. I think that, you know, our actions have consequences, positive and negative, and we can choose to accept those or not.
And sometimes we have a choice in that and it’s, and, and sometimes we don’t, and that just makes our lives harder or easier, right? All of these things filter in together. And so when you say calculated risk, how are you defining that?
Rich Kahn
Well, it’s, I’m trying to describe. Okay. So there’s that old saying, right?
What would you do right now if you knew you couldn’t fail?
Jess Dewell
Yes. Great.
Rich Kahn
Right. Very different than what would you do right now? But you have bills to pay, you have responsibilities to meet.
So to me, that’s the calculated risk. I would always make a risk. I would take a risk in, and again, this is in my mind, but on the outside, it’s, it’s seen differently.
A perfect example. I called my father one day, I said, Hey, we’re moving to Delaware. He goes from, we were New Yorkers moving to Delaware.
He goes, why moving to Delaware? You have a job down there? I’m like, no.
You have any friends down there? No. Family?
No. How are you going to pay the bills? Oh, I’ll figure it out.
But like in my mind on the flip side, so on the outside, it looks like, he’s taking a big risk. In my mind, I’m like, I’m literally under two hour drive from five major cities. Opportunities are out there.
I’ll find something. Not a big deal. I used to commute two and a half hours to Manhattan from upstate New York.
So if I had a two hour commute, it’s not that big a deal. I’ll find something. I’ll make it work.
And it was just, we just found, we just fell in love with the place. Wanted to move down here for the kids. But in my mind, I had, hey, I had five different cities.
I had calculated. But on the outside, wait, you’re moving to some place. You have no opportunity, no job, no family, no friend.
What are you thinking? And that’s kind of been my mentality my whole life, just because I’ve always had responsibilities. I got married when I was 21.
Had my first child when I was 22. Bought my first house when I was 23. Had big responsibilities early on and always had a business.
Not always, but I was always doing a business on the side at minimum. And I always had that thought, this needs to make money. This needs to make profit.
So let me not bet big. Let me bet small to medium so that I know if it pays off, I’m going to make more money. If not, I’m still making enough to pay the bills.
And I think that just hinders entrepreneurship a little bit.
Jess Dewell
Really? Being pragmatic does that?
Rich Kahn
In my mind, I think.
Jess Dewell
Okay. Well, that’s interesting. I’m just thinking, I don’t know.
I’m listening to you. And I know some of the people listening and watching are probably like, Jess, that sounds like you. We actually have a lot in common.
We actually have a lot in common. And one of the things we have in common is the conversation with a parent about moving. Mine wasn’t to Delaware from New York.
Mine was from Eastern Kansas to Seattle.
Rich Kahn
A little bit bigger.
Jess Dewell
I’ll say yes and same thing. What are you going to do there? Don’t know.
I liked it when I visited. How’s it going to work out? Don’t know.
I know it will. I was part of a company and it was a startup and that was all fine. Same thing.
Don’t know. And so my pragmatic side came out. I’m like, look, the only reason I won’t go is if you tell me I can’t come home and live with you if I fail.
And my mom said, well, of course you can come home. I said, then what? What’s the deal?
I’ll see you. And I never looked back.
Rich Kahn
Yeah. You just got, you know, but like I said, in your mind, you had opportunity, you had something and you know what? You had a fallback plan.
That’s true.
Jess Dewell
There was a little bit of pragmatism in that. I wouldn’t have done it if I had no, if I was going to, if I didn’t know how I was going to fall, because I like to bounce and I like to know there’s something to bounce from, even if it’s not a very high bounce, cause it’s a very hard fall. Right.
I’m okay with that. But I think, so I, but I do think you’re, I think you’re more, I don’t know how I think so the sake of fun. So this is the theme for you is what I’m hearing.
Not having to be pragmatic, not having to worry about what those outcomes are and just going for it because it sounds fun, regardless of what everything around us says, does, or feels.
Rich Kahn
Yeah.
Jess Dewell
That’s entrepreneurship to you?
Rich Kahn
Pretty much.
Jess Dewell
Okay. Well, Hey, I love this. That’s not how I’ve never viewed it that way.
And I think that this is a really fantastic conversation in the sense of maybe I’ve always built in the constraints and never looked at them like constraints. And so I’m hearing you and the pragmatist in you that is saying, of course, and I’ve got to succeed. There is no, there is no option.
So when we’ve got to succeed, it sounds like it changes the board game.
Rich Kahn
Changes your mentality and it changes the direction you head in.
Jess Dewell
Yeah.
Rich Kahn
I mean, I just give you another, so as I grew up in different businesses, the business I’m currently in now, I didn’t have to start. I had in my mind, I had the ability to retire from my last company. So for some, I didn’t need to, you know, need money anymore.
So I’m like, you know, I’m at a stage that life that I can finally now start a business and not worry about, you know, let’s just do it for fun and make it the best I can make it not worry about if it’s going to make a profit from, you know, month one, you know, and unfortunately the way things laid out, I had to invest. I had to put everything I had on the line for the business. And I remember thinking, ah, I trust the product.
I love the product. I think it’s going to be, I think it’s going to do okay. And like little by little, my wife and I agreed to put everything on the line.
I’m like, I turned around and I go, I don’t know how we got here, but we could lose everything. I mean, everything, we’ve got it all in the line for this company. And we looked at each other and like, do we believe in the company?
Do we believe in the product? And we both said, yes. So like, we’re here.
Let’s, let’s just work our asses off and make it do the best we can.
Jess Dewell
Okay. So, and you, and are you in the middle of it? I was going to say you’re in the middle of it, right?
Rich Kahn
We’re in the middle of it. We’re in a good spot. Company’s growing.
I’m actually able to trust my, my staff to handle it while I’m out for a couple of months. And it’s not that I didn’t, didn’t trust my staff. It’s that mentally I’m a control freak and I’ve got to have my hands on the beat of the business and not, and being forced not to do that for weeks, if not months, is going to put a test.
So I can see for myself that the team can handle it while I’m out.
Jess Dewell
Okay. Okay. So here’s an interesting thing that I, I’m like, Ooh, listen to that.
You don’t feel like you can have a beat of the business on the business within the business, if you’re not actually there?
Rich Kahn
Generally speaking, that’s how I feel.
Jess Dewell
Okay. Have you ever explored that at all? Now I’m curious.
Cause I’m like, Ooh, this is really interesting because getting out of the center of our business is the hardest thing we can do. Especially when we like to know, and we trust the people around us and we have such a good working relationship that it feels like they have all the responsibility, which is real yet. They still come and they, you want to be the one that removes the obstacles that come up because it’s probably what you’re really good at, huh?
Rich Kahn
Yeah. And that’s, I get a little taste of that when I’ve, uh, I just took a vacation recently where it’s two weeks and I check email night and day. And it’s like, I got through the whole week with really nothing major hitting, hitting the plate.
And I’m like, okay, I can do that for a but the control freak in me is it’s going to test the control freak in me.
Jess Dewell
There’s something else here and I’m trying to, I’m trying to find it because I’m not quite sure what it is. It’s eluding me just a little. Um, so you’ve been practicing to be out of the office a little bit longer and longer.
Rich Kahn
Uh, last couple, yeah. Last couple of years I’ve taken some vacations that are a little bit longer.
Jess Dewell
Yep.
Rich Kahn
Like I think last year we did a Panama Canal cruise the year before that we did an Alaskan cruise. And these are like two week long vacations where I’m out of the office for two weeks. And you know, the fact that I can connect and get my email and just keep tabs on things and nudge people one direction or another if I have to, um, this next out will be less of that.
Jess Dewell
So how long have you actually gone in days in a row without checking your email? Okay. Okay.
That’s interesting. I learned, and this is, this was an interesting thing that I faced because, um, I also know that there is so much that we read between the lines and we feel and we experienced that adds to the knowledge that we have that makes us so good at what we’re doing to get those split second decisions to understand how to adjust so that large pivots aren’t necessary. Right?
I mean, that is a part of what it means to be a vision holder and a trailblazer along the way. I, I’m, I’m all in on that part. And then there was this time that I was like, well, what would actually happen?
And how bad would it be if it actually went as bad as I thought? So I started with just the weekends and not checking my email on the weekends. That was, that was the hardest thing I’ve ever done in my life.
Rich Kahn
Like to this day, you asked me, well, I’m just getting a sweat hearing about you doing it.
Jess Dewell
And see, and I’m like, okay, it’s, it’s harder to not check my email on the weekends than it is to fight. I’m in the middle of a pushup challenge. I want to do 48 pushups in a row by the time I’m 48.
Okay. This is hard. I’ve taken a little bit of a sabbatical because of other life stuff and I’m back in it now.
And I’m like, Oh yeah, I actually was surprised I got as far as I did before. So I’m halfway there. I can do 24 in a row.
That’s where I’m at.
Rich Kahn
I tried that. I tried that challenge.
Jess Dewell
Well, mine’s I gave myself a whole year and I’m going real slow because I do, I think right now I’m up to, I’m up to like 60 pushups three times a week, but they’re in sets. So then every once in a while I’m like, well, how many can I actually do in a row? So I’m not doing 20 in a row in a set yet.
Um, which is kind of nice, right? So I’m like nice and slow. And I hate it.
I hate pushup switch. And I also know it’s, it’s not the, it’s not as hard for me to do this as it is to not check my email.
Rich Kahn
Yeah.
Jess Dewell
So you’ve done that. How did your pushup challenge go?
Rich Kahn
I was, my goal was to do 50 in a row.
Jess Dewell
Okay.
Rich Kahn
Um, and that was just to get to that point because the ultimate goal is I wanted to get to a hundred in a row.
Jess Dewell
Oh, nice. Yes.
Rich Kahn
I studied martial arts for like 17 years and one of the, I was actually invited to the 2000 Olympics to compete. Um, did not go because we had just had our second child, just bought a house, got my first big boy job. And I’m like, eh, I can’t give all this up for a couple of years.
Jess Dewell
Okay.
Rich Kahn
But I love martial arts, enjoyed it very much. Um, and one of the guys to, I, I, one of the guys I’ve ran into one of the, uh, uh, senseis, I asked him, I’m like, guy was in great shape. I’m like, all right, how, how many hours do you spend in a gym a day?
He’s like, I don’t do the gym. I do martial arts training. And he goes, I do a hundred pushups every morning.
That’s the only thing I do. And that takes care of the core, the upper body, the arms, everything that you want to take care of pushups, best exercise.
Jess Dewell
All right.
Rich Kahn
I want to get, I want to get to that, but let’s start with shooting for 50.
Jess Dewell
Yeah.
Rich Kahn
Um, cause at one point in, I was in, uh, studied four different styles. I was in Kung Fu, which is Chinese martial arts. And, um, for the black belt test were required, um, 50 pushups.
So I was trying to rework up to that again. And I got to about 40 and then we went on a two week trip. I think it was the Panama.
I came back. I couldn’t do 20. I’m like in two weeks, it took me like months to get up to that level.
And in two weeks I lost half of it. I’m like, Oh my God. It was just so deflating.
I just stopped.
Jess Dewell
That’s actually where I’m at is that over the over thing, um, is how many you lose when you stop, which makes it real, which by the way, let’s just be real. That ties back into, and I don’t like to say this because I like to help people get out of the center of their businesses. Uh, that’s, uh, but we’re talking about this and the reality is there is there, there is some sort of an art in here where you can’t fully be out of the business and actually have a pulse of the business.
You, you are either a business owner that is active and that can still be not the center and very active to have all of that knowledge or it’s inactive. And the way that decisions are made are going to be very different based off of where the seat is in relationship to that day to day. So we’re coming back to, you can’t, you’re sweating about two days of not answering email.
And I get it. I, and at the same point in time I’m thinking, well, so being able to know, because how old, how old is your business?
Rich Kahn
Uh, eight years.
Jess Dewell
It’s eight. That’s what I thought.
Rich Kahn
The technology is 21 years old. I built the first version of it myself in 2004 and five is when I started that first version and we built it in another company to solve a problem that we needed solved. So I, no, no solution existed.
So I built it myself. And then 10 years later realized we had clients asking if not begging to use it outside of our network. And then we spun it off in its own company.
It’s kind of how we spun it off. But this company has a standalone solution. April 1st of 2017 was it launched.
Jess Dewell
Lovely. Okay. So still it has legs.
You have a team. They can do it. But I get that.
How much do I lose when I go away? And what, and so then is it the test of, so how, how long can I go away and still have the pulse or what does my cadence or rhythm change so that I can keep the pulse and still have that right? Like pushups versus no other workouts.
That is amazing to me that you said one of your told you that I’m thinking, well, how cool is that? So there’s gotta be a way in business too. I’m thinking to just do one thing well, right.
And have that connection.
Rich Kahn
Are you familiar with EOS? Yeah. Okay.
So we run the company through EOS.
Jess Dewell
Yep.
Rich Kahn
So literally I think I know, and I typically, I don’t do the EOS leadership, the leadership meetings once a week when I’m out. So I let the team continue on the last instructions that we had. They have their quarterly goals and everything else.
They know what they’re supposed to be doing, but depending on how long I’m out. So I might, because I’m planning on being out for three months, I can’t go three months without having, you know, team meetings, you know, leadership meetings at least once a week. So I’ll probably take two weeks off, see where I see where I feel.
And as long as I’m up to it, do those meters, leadership meetings, just, I won’t be in person. I’ll be remote. I’m a big in-person person.
Jess Dewell
Old school.
Rich Kahn
Yeah. I mean, our entire staff is in the office except for a few people.
Jess Dewell
So, yeah, I run a completely dispersed team, but I do like to be in person as much as possible. And in fact, I build it into what we’re doing just because there is something there’s, there’s special, this is more special than email or texting or phone. Don’t get me wrong.
What we’ve got right here. And there is a deepness, a, that, that you get being in person, that even video doesn’t allow for. And we need more in a world of distraction, everything that we can do for presence becomes more.
I mean, I believe that’s our next set of superpowers. If somebody can be present and they can be without their technology and interruptions for 90 minutes, that is something very few people in this world will ever be able to do.
Rich Kahn
Yeah.
Jess Dewell
Just like very few people choose to write their goals down. So being part of EOS, you’ve got, you, you write your goals down.
Rich Kahn
I do.
Jess Dewell
Yeah. Me too. Me too.
I’ve done it. I love, actually, I really like, um, I really like what Gina Whitman put together when he originally put it, uh, when he originally put it out all those years ago. And I think there’s a lot of value in that particular kind of system.
My, what’s your, what is the thing that you turned out to need and like most that benefited you as the torchbearer, uh, in the business through the systems that you’ve picked up from EOS that you use?
Rich Kahn
Um, you know what, all the businesses I’ve had before, I’ve never had regular scheduled weekly meetings with my leadership staff and never did quarterly meetings, uh, quarterly planning. Like it just, I’m a big believer in writing down personal goals and never did it for the company and never sat and coached my leadership to put their goals in writing and hold them accountable. So it was, it was kind of just adding that layer of structure that we didn’t have, which I really enjoy through EOS.
Jess Dewell
Do you like, uh, how, how does account, I don’t know about why I said, do you like, how does accountability show up?
Rich Kahn
So in other words, someone commits, uh, so maybe my VP of marketing commits to doing a series of tasks during the quarter. That’s not like a, you know, write a blog or something like that, but like a long task, like we’re going to have a new ebook out. We’re going to have, you know, a new two new case studies out to score, like putting those down and then agreeing with the individual saying, yeah, that’s, that would be a good goal for us to accomplish this quarter.
And then at the end of the quarter of digital accomplish those goals and going down the list each week, going down the list, how are we doing on this? Is there anything I can help you with or you’re stuck on anything? You know, let’s, what, what can I do to support you in reaching those goals?
Jess Dewell
Um, how much time have you saved with that?
Rich Kahn
I think we’re more productive. I don’t know if it’s time saved, but it does reduce the number of meetings that we would have in the course of the week with leadership because we just meet once a week, everything gets done. And then there’ll be times where I’m having a conversation with someone and it’s like, you know what, let’s add that to EOS board for next week.
You know, let’s just try to minimize the number of meetings that we have. Just, just try to reduce meetings, but have more productive meetings.
Jess Dewell
Yep. I’m all about that. Less meetings, more, more on purpose.
Do you, how, who holds you accountable?
Rich Kahn
My team.
Jess Dewell
And they’re willing to stand up and say so?
Rich Kahn
Oh yeah. Good.
Jess Dewell
Hey, I love that. Kudos to you. That is something that I wish for every company.
So, um, did it change? Did it change the way you hired and onboarded?
Rich Kahn
Yeah.
Jess Dewell
Yeah.
Rich Kahn
So we now focus on certain things like it’s, you know, with EOS, it’s, they call the GWC. Does the individual get what you’re trying to do? Do they really want to do what you’re trying to hire them for?
And do they have the competency to get it done? So, and then do they follow our core values? You know, are they good with our core?
And we have very straightforward core values, nothing crazy.
Jess Dewell
Um, no, how unique are they? Come on. Tell us, tell us your values.
Rich Kahn
So it’s basically, it’s an acronym for Nora. We just decided to do something like that. So authentic.
We want people to be themselves. Like don’t hide your, like we had some people that were trying to hide who they really were. And it’s like, be yourself, like be authentic, be who you are.
We hired that person. I want that person in my company because I want the diversity. I want the, the different ideas I want, you know, what you bring to the table, be authentic.
Um, and is never satisfied. So build something, write something, be happy with it, but know that you can do a better job on it. So next time we do it, we do a better job.
So never satisfied is a good thing. Um, United, we work together as a team. We want everybody to be able to work with each other.
Um, you don’t have to be friends with everybody, but you have to be able to work with each other. So United, uh, reliable. Um, if I give you a task or somebody gives you a task and you say, I’m going to do it, I should be able to bank on the fact that it’s going to get done.
I shouldn’t have to come back and say, Hey, what happened to that project that we discussed three weeks ago? Oh yeah, I forgot about it. I don’t want to hear that.
It’s reliable. I should be able to rely on you. And the final A is a lot of fun.
Jess Dewell
I like that. I love that.
Rich Kahn
You know, our last company, we had three core values, work hard, play hard, eat hard.
Jess Dewell
Hey, they fit into the new ones. A N U R a, right? That’s five.
They fit into the five.
Rich Kahn
They fit in there.
Jess Dewell
I love that. It’s so ever evolving. That is so great.
Anara, how did you come up with the name?
Rich Kahn
So it’s interesting. So in our first company, um, my wife and I were putting together and it was back 2003. And I said, you know, we should have, we’re building up a contest search engine.
So it’s going to be kind of fun and playful. We should have a mascot of some sort. And we lived in frog hollow golf course.
So the frog became the example of it. This technology was built inside that company. So when we came out to it, we were trying to look for names.
And my wife came up with Anara. And I’m like, it’s short. It’s five characters.
Is it available? I like it. But where’d you come up with that?
Well, in the animal kingdom, the classification for frogs is Anara.
Jess Dewell
Okay.
Rich Kahn
That’s amazing. It just fits.
Jess Dewell
That’s so good. All the way around. I love it.
Okay. So now I’m going to circle back because we let this settle a little, and I want to see what pops up for you now, which is you’re going to be out of office for three months. You’re going to have weekly meetings with your team at some point after probably two weeks or so.
So now I want to know, what is the best case scenario that can happen in your mind from being all the way out of office and still being able to have a beat within your company of what is going on?
Rich Kahn
Yeah. Numbers are growing. Everybody’s getting their goals or the rocks accomplished.
And I’m stepping more and more outside the company basically by physical demand. I can’t be there. So everything continues to grow.
And worst case scenario, everything would be stagnant or the company would be shrinking. Sales are dropping, but I expect and hope things are going in the right direction. Goals are being accomplished.
Jess Dewell
Yeah. That’s amazing.
Rich Kahn
Yeah. That’s what we’re looking for.
Jess Dewell
And it sounds like, I mean, how long have you been working with EOS in Enora?
Rich Kahn
Four years.
Jess Dewell
Yeah. So you’ve got your cadence and your flow. I think that that’s something to totally, I mean, out of all of the tools and all of the systems and all of the other stuff that changes, something like that, quarter after quarter, four times four for 16 quarters, that’s actually pretty amazing to be able to lean into a lot.
And I mean, you know what the support and the expectations and the actual results of the accountability have been. And so that’s pretty cool too, because one of the things I love about a cadence like that, and you can, you can tell me that this is also the hardest thing. It’s easiest to say it just helps you and you can lean into it.
But the hardest thing is actually going, okay, so what is it showing me? And am I really going to accept what it’s showing me? And do I want to improve that way?
Are we going to do what it takes to do that? And how does that actually impact what our end goal is when we put ourselves out of business all these years from now, or when we, so we can show up to a, whatever new opportunity might need an immediate response versus waiting until the next week’s meeting or waiting until, you know, the next quarter or year being able to have that confidence to wait, to wait. I think some people, I think some, you tell me how you feel about this.
I run into businesses and business owners. And by the way, I fall into this category too, which is probably why it’s easy to see. I will wait because I don’t know what to do versus waiting because I know the time is not right.
Rich Kahn
Interesting.
Jess Dewell
How does, how does that show up for you?
Rich Kahn
More like waiting to see what’s going to happen.
Jess Dewell
Okay. So a little bit of a middle.
Rich Kahn
Yeah. Somewhere in that, in that midstream of that, I think.
Jess Dewell
Yeah. Interesting. So talk to me about, I’m, I’m really interested.
So knowing you’ve got this cadence and you’ve got this stuff and you’ve got your expectations and you’re growing and we’ve got all this awesome stuff going on. How do you reflect?
Rich Kahn
Generally, I get into the office, get my morning meetings out of the way. And I usually have a set time where I’ll just sit down, got a couch, lay down and just, all right, what do I want to accomplish today? What’s, what’s my goals for today?
And that’s kind of my reflection period. Every day. Yeah.
I say four days a week.
Jess Dewell
That’s good.
Rich Kahn
Yeah. Is that your work week? Yeah.
Jess Dewell
Nice.
Rich Kahn
No, no. I have five days of work week, but something somewhere during the week and usually it’s my EOS meeting because I have my morning meeting and it goes straight my EOS. And by then it’s now 10 o’clock and my day’s just going.
So that’s generally why I say four days a week.
Jess Dewell
Oh, well, but so you’re doing it with your team instead. So I’m going to call it still five days a week.
Rich Kahn
All right.
Jess Dewell
Because you’re, you’re bringing your team into one. How about that?
Rich Kahn
Right.
Jess Dewell
And that’s, and that’s a big deal when you’re building a company that’s going to grow and stand on its own with you, with you standing, looking at the garden instead of being one of the flowers in the garden. I love that. Right.
Okay. So that’s interesting. I spend, I spend several hours one day a week to, to work on things.
And then I’m just in the midst of it. So I have some concept of what needs to occur in a week or in the next, in four weeks from now or whatever it is. And then that changes and adjusts week to week.
But you know, my, one of my biggest things, and you’ll have to tell me if you don’t have this problem, I want to know if did and you solved it, which is, I love to say yes. I love to give freely of time and what I have to do every single week as part of my strategic time, which I call a present retreat. I am, I’m, I’m getting rid of meetings on my calendar.
I’m getting rid of things that I said yes to with complete humbleness because they don’t match, they don’t line up and, or they’re not the right time. And I have to, so I have to free up time every single week so that that deep work can be done. And the actual things that need to occur can really occur.
Have you ever had that?
Rich Kahn
I’ve had that, that times where I say yes a lot to just bring on the meeting. Cause I’m like, yeah, I’ve got plenty of time. And also I walk in, I look at my daily schedule.
I’m like, I’m not going to be able to go to lunch. I’m not going to be able to, yeah. To the bathroom.
I’m like, we got to fix this. And then I’ll go into the people’s calendars where it says reschedule and I’ll bounce it out to a day that’s not too busy.
Jess Dewell
Yeah.
Rich Kahn
Some, some people I’ll email and say, look, I just got double booked. I can’t, I can’t make it. I just got to free up some, some free time to get stuff done.
Yeah.
Jess Dewell
Yeah. Okay. So talk to me about the, like when you are thinking about the indicators you’re using in your business for success, the ones that you’re using day to day, will you share those with us that you know that you’re on track or not?
So we got to pause and spend more time here or, Oh, we’re off priorities. So let’s rearrange it this way. Do you have indicators?
I’m going to go all the way back to that, that pulse of business that you are so into when we were talking at the beginning, what are the things that you’re leaning into that cause you to pause and go cool or let’s spend some time here.
Rich Kahn
I generally don’t do that.
Jess Dewell
Oh, you don’t. Okay. I don’t think so.
Rich Kahn
I just, I just pushed through. Cause I guess when we’re doing the planning, we don’t over plan for too much to get accomplished. So I’m not, I’m not backtracking on some uncertain things.
Jess Dewell
Okay. How many opportunities do you say no to in a week?
Rich Kahn
Handful.
Jess Dewell
Okay. Versus how many do you get?
Rich Kahn
I’d probably say I’d probably get a dozen opportunities a week to different things that I’m looking at and I’ll probably accept about half.
Jess Dewell
Yeah. Okay. Yeah.
How does that feel good? Does that feel, does that feel right for you? Does it feel out of balance?
Rich Kahn
That feels balanced.
Jess Dewell
Yeah.
Rich Kahn
Like I’ve done it before where I’ll get 10 or 12 opportunities in a week and I’ll say yes to them all. And then I’m like, what was I thinking too much? Cause I can’t do, I can’t, I can’t say yes to everybody.
Wouldn’t that be nice? Yeah. I’ve had the time and the resources, but you know, we’re a team of about 30 people, so there’s limited resources.
Jess Dewell
Yeah, totally. Well, all right. So what do you think, I’m going to ask you forward.
Look, how about actually I’ll start here. What’s the most surprising out of your business from 1993 to now with all of the businesses and the 32 years specifically in digital marketing, what is the thing you were most surprised by? And when was it?
Rich Kahn
I guess a couple of things, but the one that I can think of is in 2000, when I had that company sold and the dot-com bubble bursted, my reaction to losing a $60 million deal when I was 28 years old was not like I thought it would be. I was like, okay, not a big deal. It really wasn’t a big deal because we’re making so much money as a company.
We had such a great direction that we were heading in that losing that deal wasn’t, wasn’t a big deal. And I was, I’m shocked with my response to that. And I remember it because I’m, I remember sitting, I remember the dot-com bubble bursting on the 14th, we were supposed to close on the 28th and the buyer said nothing for like a week and a half.
And me and the partners are like, something’s got to get like, they’re just not moving for like the whole premise is they were going public. And because they were going public, all this money was going to be available and blah, blah, blah. And we were trying to sexy up there, but they were just a consulting business.
So they didn’t really have anything dot-com sexy. And we were that dot-com sexy at the time as we were paying people to surf the web. So there was like some sexiness there and they needed us.
And I’m like, something’s got to give. And then all of a sudden we got the call, Hey, they’re their CEO want to take me out for lunch. And I’m like, okay, here’s where they talk.
Here’s where the deal comes off the table. And when it happened, I thought, you know, I remember leading up to that meeting, I thought, oh man, this is going to suck. We’re going to lose this big deal.
We’re only 28. How cool would it be to sell your first company when you’re 28? And when he said it, I’m like, and he says, we can still do the deal with all the cash is off the table.
I’m like, well, then there’s nothing there for us. Like I’ve got cash coming in. Why would I give that cash to you and not get anything back in return?
Not a big deal. Like, you know, this, when this storm weathers and we could talk about it down the road. And I came back to the, to the team and I’m like, yeah, it came off the table.
Like we thought, and everyone’s like, well, how do you feel? I’m like, I feel fine. Like we’re bringing in a ton of cash.
So there’s no cash on the tables. So like, to me, I was shocked at that response of myself.
Jess Dewell
Yeah. Looking back, how does it, are you proud of yourself for that response?
Rich Kahn
Yeah. Cause like I said, we were making a ton of money, so it didn’t make a big deal. However, hindsight, the whole.com kind of crashed and our business went with it over the next several months. So if we haven’t, would have cashed out, we would have, I mean, cash in hand. Right. But you know, we’ve led it to, it led me to another business, which did really well.
And that led me to the next business. So like each one was a learning point and each one led me to the next business.
Jess Dewell
As you were switching from business to business, is there a common trait that took you there? Was it instinct? Was it what I’m interested enough to do it within the constraints I have?
Was it something different than that?
Rich Kahn
It was having to pay the bills. I mean, it wasn’t anything grand, grand, you know, it was just, Hey, I’ve got to pay the bills. What can I do right now to pay the bills?
And honestly, the business I’m in today was the first one. We didn’t start with that mentality because we kind of solved that problem with the last company. And it was just, Hey, let’s just, people are asking for this product.
It wasn’t a product that we had planned to sell. I even took my last company through a process to sell the company, spoke to Google, Facebook, Yahoo, Microsoft, and about a half a dozen other big companies. And they all said the same thing.
They didn’t care about my other company. They really liked the fraud detection solution that I had built in the new company. And they all asked the same two questions.
Is it a standalone product? Do you have clients behind it? And I had to say no.
And they all said the same thing. Once you do call us back. So get kicked in the head once in a while.
And you said, okay, this is what is valuable. This is what clients want. Let’s build it.
And we did. And it didn’t, and it was one of the first companies I built that didn’t, I wasn’t worried about the finances because I had another company that was taking care of my finances. So let’s just build it because we can.
Jess Dewell
So you’ve already started down this path of what you want to do next with even less constraint in the future. That’s what it sounds like, right? You’re on that path of building.
So is that what success looks like to you?
Rich Kahn
Success to me, I guess, looks like when you’re, when you’re working on a project and not worried about the finances. That’s a level, that’s one level of success because then you’re not, you’re not confined to the bottom line. Is it making a profit?
Can I pay the bills? Like to me, that was always something I was always concerned about that. I grew up on welfare when I was young.
I never wanted that for my family. So that became ingrained in my head. How do I build something that’s going to pay the bills?
Jess Dewell
Yep. Yep. That’s, I also share with you, there’s something incredibly special and strive and protect everything I can for my freedom that money brings, that I don’t have scarcity, right?
There’s something going on. So I share that. I’m saying a whole bunch of different words, but I share that with you.
The freedom, I want freedom of money. That is something I hear you saying and that resonates deeply in my heart and in my gut. Where do you make decisions from?
Do you make decisions from your head, your heart, or your gut? I’m a gut girl.
Rich Kahn
I’m a head guy.
Jess Dewell
You’re a head guy. Well, it comes back down to that. I’m going to call you pragmatic.
You are not using that word. I am using that word. I am making decisions with known constraints and they are a priority, which is fantastic.
Yeah. All right. So now I want to know what makes it bold.
I want to know what makes it bold to know exactly enough about yourself and the way you operate in the world to be able to achieve your goals and success. I don’t know. I just made it up.
Rich Kahn
I’ll tell you.
Jess Dewell
Everybody who’s listening knows I make a bold question, everyone. I didn’t know what ours was going to be. So here’s where I was going to go.
Let’s try again. We’ll build it together. Maybe you have a better question, which is this.
I was thinking about what makes it bold to let go of some control knowing all of the work you put in results in success over and over and over again. That’s your past. Your past is I’m going to do it.
I’m going to pay my bills. I’m going to build. I’ve got a new skill.
I’m going to go do this again. And I’m going to keep doing this within the constraints I have and the obligations that I have accepted and want in my life. But then I was thinking, well, you know exactly what you want when you make a decision.
So maybe is that what makes it bold? What makes it bold to know exactly what you want to be able to make those decisions because it will result in achieved goals and the successes you just defined it?
Rich Kahn
So I’m thinking, and that’s kind of what this next couple of months for me is going to be, is the next level of success for me is stepping away from the day-to-day business, checking email every 30 seconds, right? Staying on top of the details of the business and watching the company that I’ve built continue to do what everybody knows what to do without me being involved, I guess is the best way to put it. To me, that’s that next bold statement of growth for me is, and it’s more, and it’s always been personal, never been the business.
I’ve always had a good solid team behind me. All the businesses that I’ve had, once we got to a point where we started hiring people, we always hired good people. Or I should say we always hired the wrong, because every time you hire somebody, you’re always hiring generally good people, right?
But it’s hiring the right person for that seat. Are they doing what they’re supposed to be doing? Do they get the business direction?
Are they a company person that really wants to focus on seeing the business grow? And I can say that about my staff. My staff is, they love to see the product get better.
They love to see the clients that call up and, oh my God, you transformed my business with your technology. They love to hear those stories. So we try to share them as different departments get that story.
So if customer success gets a story or salesperson gets that, or developers, I hear from different trade shows that I go to or different business meetings that I go to. So we try to share those stories so everybody gets that, but they all thrive in seeing the company do better. So now it’s watching the company get better without me is more of a me thing than anything else.
And I think this next forced outage for me, this next forced time away from the company is going to prove that to myself.