Ep. 29 Become a Dadpreneur to Escape Employment with Adam Dukes

I'm really excited about today's interview with Adam Dukes. He is a father of two, a dad-preneur, and a marketing strategist. I'm excited to have him discuss with you specifically some things regarding:

  •  How to focus,
  •  How to simplify
  • How to overcome the fear of failure, and
  • How to overcome imposter syndrome.

He's been in the online business space for quite a while, and has a lot of good information to share.

Now, he is a horrendous fantasy football player, a dreadful golfer, a cheeseburger connoisseur and a waste bucket full of useless sports knowledge.

Aside from that, he has really good advice on how to be a freelancing dad, how to earn money from home while supporting a family, because he has done it himself, and he has also talked to a lot of other dads who have done it.



There's a lot of mindset blocks that we tend to have when we are providing for a family, and we’re attempting something very new, something that a lot of people aren't used to.

Working from home, working for yourself, and being self-employed is the road less traveled.  

Because of that, you're going to have some naysayers in your family circle or friends. Maybe your own spouse is doubtful. And there's a true fear there that you're going to fail. That you're going to put your family's financial security at risk.

There's a lot more at stake when you're pursuing this type of career while raising a family than when you're single or you're in college or living with parents.

When you’re single, you have your own finances. It’s still a worry, but it's much less pressure. So you want to make sure that you transition into freelancing the right way, and you need to be aware of the fact that there will be some obstacles in your own head that get in the way of you being able to find success as a freelancing parent.

Our goal is to talk about how to freelance as a parent, how to build up a business from home, and how to work at home so that you can have more time with your family. We also talk about how to support your family doing what you love and what you're passionate about.  



With that I said, I’d like to welcome Adam Dukes. I'm really excited to pick your brain today for our freelancing dad audience.

I wanted you to introduce yourself and tell a little bit about what you have done as an entrepreneur and as a freelancing dad. Tell us how you have been making money and supporting your family, and a little bit about your story to catch us up a bit for those that haven't heard of you.



Sure. I moved out to Vegas in 2006 from Michigan. I had a degree in construction management working a couple of years and then in 2009, I got laid off with the tough economy.

In February of 2010, I bought Gary Vaynerchuk’s book, How To Cash In On Your Passion. (Crush It: Why NOW Is The Time To Cash In On Your Passion)  I bought that book even though I wasn't planning on being an entrepreneur. This was pre dad, but I bought that book in February of 2010 because I saw a video of him. He was just very outspoken, very brash, but I liked his style even though I wasn't looking to be an entrepreneur.

So I read that book and it kind-of became my gateway drug into the online entrepreneurial world. Then I got the Tim Ferriss four hour workweek book. (The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich) 

When I started my entrepreneurial journey, I started with selling website design to Las Vegas businesses.

I had never cold called a day in my life, and I had never sold anything a day in my life. 

I used to take a shot of vodka before cold calling to calm my nerves. I was not good at it. I was, I was horrible at it.

I called 5,000 Las Vegas businesses and sold two websites. That's how bad I was. I didn't connect with 5,000 obviously, but I did that for probably about five years. Any type of digital marketing service to local businesses was how I got my feet wet in the whole online entrepreneurial world.



Gotcha. Very cool. It's interesting to hear people's stories and how they got started and how it always ends up transforming into something else.

I think you realize from the get go that you want to stick to this. Obviously it's a struggle and there’s things to figure out, but the overall lifestyle that you get from freelancing work instead of being an employee definitely hooks you in and it's hard to turn back even if things aren't going well.

That was my story. I was really struggling for a couple of years and even though I wasn't gaining momentum financially, I was so deep in it. There really was no going back in my mind. I couldn't go back to a typical employee job because I knew that if I did, I wouldn’t be able to keep pursuing this freelancing lifestyle. I wouldn’t have the time.

So, something that I've experienced personally, and I know a lot of dads and parents have experienced when they’re working at home or trying to build up a freelance business to provide for their families, is the fear of failure.

You fear that you're going to risk too much, that you're going to put your family's financial security on the line. And if you fail, then it's going to set you back even more. Tell us a little bit about your experience with this and any advice you have for overcoming this.



Last summer I hired a mentor, and one of the first exercises was to interview 50 people in your target market. It wasn't a sales call in disguise,  it was purely market research. It took probably three and a half to four months to get it coordinated. But in June of 2020, I talked to 50 dads about starting a side hustle or online business. A lot of people were still at home with the pandemic, and a lot of people were either laid off, fired or their hours were drastically reduced.

Six months prior to that, they had no idea that they would be dealing with these circumstances because of the pandemic. So a lot of the dads I spoke with had zero online business experience or side hustle, they were just kind of frantic about what they were going to do.

Out of the 50 dads I talked to, the biggest thing I asked was “What's your biggest problem? What's your biggest frustration?”.

42 to 44 of them said fear of failure was the biggest one.

It was close to probably 90%. And it was interesting to hear that, because I feared that as well, years ago. I've gotten better at it, not to say I've completely got away from it, but I’ve gotten better.  

I looked up these stats as an example:

I compared Kobe Bryant’s and Michael Jordan’s field goal percentage.  Kobe’s was 44.7% and Michael’s (the best of the best) was 49.1%.

Michael actually missed more shots than he'd made. Unfortunately, I think LeBron James is 50.1%, so I can't use him as an example.  

But the point is, it's part of the process. It's that feedback. You hear those clichés all the time. You see the memes all the time, that feedback isn’t failure, and that it's not final, but they're clichés for a reason. It's getting over that fear of failure.

Honestly, I believe it's not the fear of failure that holds people back. I honestly believe it's the fear of judgment from others. 

If they do fail, whether it's their wife, whether it's their boss, whether it's their coworker, whether it's their parents, whether it's someone they went to high school with 15 or 20 years ago, what that person might think or say about them, if they do fail. So I think that fear of judgment is a really big one.



Definitely. I'm glad you brought that up, that we fear how other people are going to react and that judgment from others.

Maybe there’s other things that we're fearing beneath that fear of failure. How are we defining failure? In your experience, and the experience of the dads that you talked to, how is failure being defined?

Tell us a little bit more about what you've heard expressed about failure. Are there other parts of this besides “I failed because I didn’t earn enough money this month?”



A lot of it was impostor syndrome, fearing that they're not good enough in whatever it is that they're going to do. And of course you're not going to be good when you first get started at anything. I joke around about things like riding a bike and kissing a girl. We were all really bad at that when we first started, but with enough practice you get better at it.

Impostor syndrome is a big one, being worried that you're not good enough. 

I read that studies show 70% of the population struggle with imposter syndrome. Tom Hanks, Ryan Reynolds, Serena Williams, the CEO of Starbucks, all those people still struggle with imposter syndrome, and they're super, super, successful. Some of them in their Oscar speeches are like, why would you even pay to watch a movie of mine?

They were winning an Oscar, but they still struggle with it. So I find a lot of people still struggle with the fear of imposter syndrome, but the successful ones are the people that overcome it, or at least they're better at managing it.



Yeah, definitely. And, that's true. That is something that we continually experience, especially when we decide to go to a new level and we decide to get out of our comfort zone again. We don't just have to conquer impostor syndrome once.

We get out of our comfort zone, we gain a new skill, and then we do it again and again, and again, and each time it's almost as if we hit a new set of limiting beliefs that hold us back.

I know with myself the biggest fear that I had was that I was afraid of my wife more than anything else. We had already decided that she wanted to stay at home and be able to be a full-time mom, so that expectation was there when I became a new dad.

I had some naysayers, family or friends that were like, that's not a real job, or you're not gonna make enough money doing that, but I almost didn't care as much about that as I did my wife’s expectations.

I wanted to be able to provide full-time income for my family. And there was that expectation from her to be able to provide for them. I wanted to show her that I could do something I loved, but at the same time that I could actually make it work financially so that she's not stressing out that we can't pay bills.

Ultimately she knew that it was in her best interest, that I'd be able to spend more time with them and so forth and have more flexibility with being with the family. But there was definitely a lot of fear there regarding, well, what if I just set us back even further instead of move us forward? It really holds you back until you overcome it.

What are some ways that people can overcome that fear? What are some, some strategies for dealing with it?



I was a little spoiled, because I started the entrepreneur thing before I was a dad.  I mean, it was a rollercoaster, but I wasn’t as serious back then because I was just supporting myself.

Then once my daughter was born in 2013, it was kind of like, oh, okay, this is, this is real stuff. And then once my son was born in 2015, it got really, really serious. So that kind of kicked me into gear. However, if it's someone who's already a dad getting started. I think picking a side hustle, and working on that on the side is the best way to go.

You really can do it in like 30 minutes a day. I mean, you're not going to quit your job next Tuesday, obviously, but it's enough to give you an edge.

My favorite book of all time is The Slight Edge. (The Slight Edge: Turning Simple Disciplines into Massive Success and Happiness, Jeff Olson)

And it's just about little daily disciplines each and every day, you know? It's just that little 30 minutes you squeeze out of the day to work on your hustle.

I tell dads, wake up 10 minutes earlier, go to bed 10 minutes later, find 30 extra minutes of time. 

Look on your phone and check how much time you spend on screen time. A lot of people say I don't have time, and parents especially, but just carving out 30 minutes of time helps you start to get a little bit of momentum.

I find momentum and confidence go together.

For most people, like 90% of men and women, it's a lack of confidence in themselves and their ability to do it. So if you can just start gaining a little bit of momentum, it's the snowball down the hill.

It's just that little bit, that little bit, that little bit, and in three months, six months, maybe in a year's time, maybe you can have the conversation of stepping away from the job. That little side hustle that you started as this little, little snowball, now it's this big snowball at the bottom of it.



Yeah, definitely. That's a good point that it's not just about jumping all in because it is going to take time to really build that up anyways. It really comes down to that learning curve for a lot of the skills you have to develop.

For me, I really lacked any kind of networking skills or sales skills. But I had started out as a freelance video editor and I was really good at video editing. I had a technical style. I'd been doing it since I was like 12, and I really knew how to put together a video very quickly and creatively, but I had no idea how to sell that skill.

I had no idea how to talk to a potential client and enroll them in my services. And so that's what really held me back more than even that the actual skill that was sellable.

It took time to just slowly build up that confidence to be able to find success there. And I like how you brought up waking up earlier. Even if you just woke 30 minutes earlier and put a little bit of time in every day.  

If you do have a full-time job and you're trying to make that transition, that's what it takes. It's that tiny little bit of extra you're doing that you haven't done before. That really adds up over time. Are there other limiting beliefs that you've seen people have that really stop them in this position?



Especially as a parent, the two biggest ones are I don't have time, and I don't have money. Those are the two biggest ones I hear.

The time one we just talked about. And here's the thing with the time thing. If you can find 30 minutes in a day, what I find is that when you start building momentum around something, you suddenly find more time.

So it was a little side hustle, but now it's easier to get up an hour earlier because you've got some momentum on your side, you know?

You said, “I don’t have any time,” and six weeks later, all of a sudden you found an extra hour, because things are starting to move in a certain direction.

I don't have money is another big one. And I, I just think that's an excuse too.

I mean, there's some online businesses, obviously you need capital and all that, but there are a lot where you don't need that.

For any type of freelance, you need the internet, your phone, and a computer. If you don't have that, you can go to the library and use it.

So, I want to eliminate any excuses of, “I don't have money” because you really don't need money. I mean, with something like TikTok, you can get up and record yourself on any subject matter you want to talk about and you'll have people reaching out and asking, “Hey, could you help me?”

If you're good at sales or marketing or any type of freelancing where you could coach them, consult them or offer that service to them, you can build up a following rather quickly. That's why I use TikTok as an example.



That's really great. And yes, I think we have this misconception that as an entrepreneur, it means you've got to have this huge investment fund. We watch shark tank and think that’s what it is, but that's only one type of business. We're not inventing a product that we need this whole team around to try to launch.

You're working from home. You have a computer, you have the internet. And it's very easy. One thing that I found was key for me in being able to get my hours down, where I'm still earning enough money to support my family, but I'm working around 25 hours a week instead of 40 hours a week was learning how to focus.

I would love for you to talk about some of your strategies regarding how to simplify the process of building up a business, how to focus, and how to approach your time appropriately.



Steve jobs, Warren Buffett, Bill Gates. If you listen to their past videos and audios, focus is like their secret word.

I really think that is the secret: focus and discipline. 

Especially with online entrepreneurs, there's so many opportunities, and you can get lost. I'm old school:  I've tried the apps, I've tried Excel spreadsheets, and keeping track of the spreadsheets. But I'm old school. I print a sheet off every Sunday night. I have it broken down into four kinds of buckets.

  • I have a mind:

So I journal, I meditate. I visualize, and I read every day.

  • I have health:

So I’m in bed by midnight, and I have a fruit smoothie every day. I have to track this and I have to put an X down to mark it off.

  • I have a section for a relationships:

Dinner with the kids and having dinner with the family. I'm really big on family dinners at the dinner table, no TVs, nothing like that. I read to them every night before bed. We try to go on a walk go to the park and do something, some kind of play. Not a video game, but play some type of a board game, or something like that.

  • And then I have my work stuff.

Right now I have to make one TikTok each day. I have to make an offer, and I have to do a TikTok live. This is how I stay focused.

I read the miracle morning by Hal Elrod back in 2015, (The Miracle Morning: The Not-So-Obvious Secret Guaranteed to Transform Your Life - Before 8AM), and then The Slight Edge, back to back. That really showed me the value of these daily disciplines. I've been doing this pretty much every week since 2016.

So then I tally it up at the bottom. Last week I tallied them, and with the holiday it was a little bit different, but I did 54% of my tasks. Last week was not good for me. So I'm not always on top of things, but my goal is to get to 88% each week. Last week I fell really, really short, my daughter's birthday was last week. So things just kinda got put to the side, you know? But that's how I get so much stuff done. People ask how I'm so disciplined and how I get things done. How I put up two YouTube videos a week, a podcast a week, and the answer is this little boring piece of paper with an ink pen. That's my so-called secret.



You know, that's great. Thank you for sharing with us exactly what you're doing to have that focus, and to be very productive, because it is so important when you're trying to balance a family life and personal activities and priorities that are really meaningful with building a business that also requires a lot of tasks and a lot of things to do. You have to be so organized in that way.

 One thing that I've wondered and I know others might be wondering as well, is how long does it take to see some results when you’re doing all of these little things? 

Because the biggest thing that trips us up is when we’re doing a bunch of stuff but we’re wondering, “is this working?” “Is this getting me anywhere?” “Should I keep doing this?” “Should I not keep doing this?”

How do you evaluate that? Because some things take months and years to gain the result that you're expecting. But if you stick with it, it really adds up and it has a compound effect. How do you evaluate your progress? And how do you evaluate whether what you're doing is worthwhile to keep doing, even if it's not bringing an immediate result?



Yeah. I look for the quick wins, the little wins. I'm big on the idea that there's no such thing as a little win. A win is a win. 

So let's say if I was trying to do some type of outreach for some type of freelancing type of work, and I was maybe making cold calls.

I don't do cold calls, but if I was making cold calls, and if I made a hundred calls, did I get through the gatekeeper? What percentage of those I’m successful with might be worth looking into. Maybe if I'm sending cold emails out, and I sent out a hundred emails, I got zero responses. Okay. I need to tweak my strategy. Then I'd send out another hundred. Okay. I got three responses. I didn't close any deals yet, but I did get three responses. Next hundred maybe I got a phone call: I got four responses and I got one phone call.  

So it's just that little bit, little bit that those little wins.

Then it’s, I closed a deal! Okay. I closed the deal, and then all of a sudden you work your numbers to figure out: every hundred cold emails, I'm getting on the phone with three people and I'm closing one deal.  

And then it just becomes a simple math problem. With the online world, if you have a sales funnel and things like that, it's just how many people got to the landing page, gave me their name and email, how many people in the follow-up emails booked a call with me and how many people bought.

There's a couple of stages of numbers where you look at it, and you just kind of tweak it along the way. I'm kind of a nerd with these spreadsheets. Google sheets is probably one of my most used software for tracking everything like that. I’m always trying to know my numbers, it's not the sexy part of the business, but it's important.



Yeah. It's important that you said that, because there's a lot more numbers than just sales. When we jump the gun and when you're sitting there expecting that success only means getting sales or a new client, and we get hung up on that, then we think we're failing.

But no, you're not failing. You got some responses to some proposals you sent, and you got some visits to your website. So I'm glad that you mentioned the importance of claiming those little successes.

I say “little”, but really they're very significant because they all add up to results that really help you to grow your business. So thanks for bringing that up.

My story is similar, because at first I was too caught up in the bigger results. I kept not getting that specific goal and I didn't realize there's all these little goals in between that I needed to focus on more.



Yeah, like you said, sales isn't the only number to focus on or the only metric to track. There's other little things that lead up to that if that's the end goal.



Yeah, definitely. Do you feel like there's anything else that would be valuable for this audience that you wanted to share with us today?



I think mindset is the biggest thing. 

Business is 90% mindset, 10% strategy, tactic or luck. I think that’s life. I mean, it's up here, you know, and we're all just a Google or YouTube search from solving our problems. I don't want to say every problem, but 98% of problems that we face.

I've taught myself just about all I know about website design, YouTube, SEO, and sales skills on YouTube or from a Podcast. All the how-to information's out there. But it's our minds that hold us back. The fear of failure, the fear of judgment, the impostor syndrome, the self doubt.  It seems like those are the four main ones.

I heard a quote by a guy last summer and it was about impostor syndrome and I've shared it a hundred times.

His name's Sean D'Souza, and he says with impostor syndrome, to pretend you're a third grader teaching a second grader. Meaning you just have to be one step ahead of the person that you're teaching.

You don't have to be the best, because chances are, you're not the best at whatever it is you do. 

You're probably not going to be the best of the best. There's going to be someone bigger, better, faster, and stronger, but that doesn't matter. You're not teaching the best of the best. You're teaching someone a step behind you or 10 steps or 50 steps, or whatever, so you don't have to be the best of the best.

And then there’s another mindset shift that I make for putting out content into the universe, whether it’s a blog, a podcast, a YouTube channel, or on social media. I truly believe this, and it's just kind of a mindset shift that I made to overcome the fear of judgment. How I look at it is this: if I don't make that TikTok, or put out that YouTube video, or write that email, there could be a dad in Jacksonville, Florida that needs to hear that message today, but I’m failing him by not putting it out there.

That motivates me to put out the content, be vulnerable, share my wins, and share my losses. A lot of my content is my losses, because I have a lot more of those.  I don't know if there’s a dad in Jacksonville who needs to hear my message, but what I can control is my output of putting out that content and helping that dad or person. That's the mindset that I have.

A lot of people are afraid to get on camera and put themselves out there.

I get it, but think of the person that you could be helping or the 27 people, or the 300 people you could be helping. I think I'm being selfish by not putting out content.



You're caring about the one and it's really easy to lose sight of that. I'm really glad that you talked about the dad in Jacksonville, and that sometimes we get caught up in these social media numbers.  We think, oh, I didn't get a thousand views on that video or on that social media post.

 Three views: that could be three people whose life just got altered because of the message that you gave them. That's a big deal.

As a freelance video consultant, I help companies to build up YouTube channels and figure out video strategies and so forth. I've worked with a variety of clients where the most common issue that people have had is thinking, oh, only 20 views, this isn't working. I can't deal with this.

The ones that have stuck it out eventually get the return they're expecting, but it's because they cared about the few people that were paying attention. And when you care about those few people that are paying attention it really goes a long way and it shows where your heart is.

When you're like, “I don't just care about having this huge audience, I just want to change somebody's life.” Even if it’s just one person, even if you just put all this effort into creating this video for one person. And so I'm glad that you demonstrated that, and that you demonstrate that in what you do, and you really set that example for caring about that one person.

Thank you so much for our conversation today, Adam. You shared a ton of value in a short amount of time that I know that we can all benefit from. Any freelancing dad and freelancing parent out there will be able to apply what you've shared about your experience and grow their business with that. Can you share with us how we can connect with you or how we can follow you in your, in your content and your videos? Where should we go?



Yeah, my site is That’s pretty much what I keep updated the most. I just recently launched a podcast myself called DadPreneur Freedom. It's not  an interview type show, at least not yet. Our audience obviously would overlap, but it’s just about helping to mind the minefield of the online business world. It’s for helping other DadPreneurs.  A lot of what we just talked about was from episodes I've already done.  But yeah, would be probably the best website and that has links to podcasts and YouTube channels.



Well, definitely go and check him out there at  

I hope you really enjoyed this interview with Adam Dukes. I certainly did.  

I learned a lot about focus and overcoming the fear of failure. And about questioning what failure even means when you're a parent and trying to pursue the self-employment route. Be sure to check out Adam's website and follow him on YouTube.

If you like these types of conversations, if you're a freelancing parent, if you're trying to raise a family and change careers from being an employee to being self-employed, then stick around, subscribe, and check us out on YouTube under my name, Chad Gravallese.  (

Hopefully you enjoy today's conversation and I'll see you next time.

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