Check out our episode with Keith Roberts, Entrepreneur | Author & Keynote Speaker | Creator of the Oak Journal.  

We chat about creativity, mentorship, entrepreneurship and so much more/—-more—-

Katty: I’m so excited to interview a good friend, Keith Roberts, an incredible creative and the creator of The Oak Journal, for this session of the Artisan Podcast. Hello, Keith, welcome.

Keith: It’s an honor to be here, thanks for having me.

Katty: I’d love to start the conversation, Keith about you as a creative and how you got your start and then we’ll make that move into where you are today with The Oak Journal.

Keith: Great. So my start, I actually went to Brooks Institute of Photography in Santa Barbara, California, where I got a degree in Industrial Scientific Photography with a minor in Undersea Photography, so really applicable to the real world….sarcasm there!  

I think one of the many gifts that I took away that was a life changer for me with Brooks was the level of presentation and professionalism that was required. It was easy to get into Brooks Institute of Photography, it was incredibly hard to graduate. There were 58 students in my class and 12 graduated. If you got to C you failed, you had to retake the class. A second C you were expelled. 

So they were really about making exceptional artists and not about just making money, which I really appreciate, and being somebody that’s owned an agency for 25 years and seeing what a lot of the schools turn out now that are based on profit versus not, really instilling what the students need to have a successful career as a creative. That was enormous for me. The other thing that I took away from that was, you know, a very special relationship with the founder of the school, Ernest Brooks. I minored in Undersea Photography and I got to spend several months living on a boat diving every day with a gentleman who has, you know, an exhibit in the Smithsonian Institute for his underwater photography. We had Jean-Michel Cousteau, Jacques Cousteau’s son, dove with us for several expeditions. So the taste for once-in-a-lifetime experiences, I got at a very early age.

Katty: Oh my gosh I got goosebumps. That’s incredible to have that opportunity at such a young age, that just opened up the whole world for you to be able to look at everything through their eyes too.

Keith: Yeah, and I would say it also set an expectation that I did not want to have an ordinary life. I remember to this day at my grandmother’s trailer in rural Indiana she had a poster of the poem, The Road Less Traveled. And I always remember that last verse “Two roads diverged in a road and I took the road less traveled by and that has made all the difference” and that was an early opportunity to see when everybody else is sitting in a classroom or working on being an engineer, which was the safe job in the 90s you know, and my dad was an engineer, and that was the safe route to go..what was possible if you really followed your passion.

Katty: Beautiful. And I know that, unfortunately, Ernest Brooks passed away recently. And you wrote a beautiful tribute about him. Can you talk a little bit about mentorship and just kind of what that meant for you to be under the tutelage of this incredible person?

Keith: Absolutely, and thank you for giving me the opportunity to continue to honor Ernie. He was one of the many mentors that I’ve continued to work with. It was a gift and I think, realizing as a Buddhist, I believe that there is no such thing as a coincidence, but when the student is ready to teach her presents itself and I think there are so many lost opportunities when people don’t realize that there’s this synchronicity happening all around them. 

And so, with Ernie Brooks, I remember something specifically said that the boat we lived on was “Just Love.” and he said, “The time we spend upon just love is not deducted from our lives.” And it still chokes me up to this day, and I think that’s why he lived to be as long as he did is because he spent so much time on that gorgeous boat. 

But mentorship is essential and it’s not something that ends with the first. Ernie sent me on a path, but at Brooks, I met Lapsom, who was somebody that worked with the Dalai Lama, and he put me on a path from being a devout atheist to finding Buddhism and changing the entire path of my life. Even though Lapsom was very briefly, in my life. And then there was a gentleman, Dave Larsen. I assisted a couple photographers Vic Huber and Bob Carey, those were also mentors that helped me continue to push what I wanted to be as a professional, but when I broke out and started working as a photographer, stock photography was really decimating the market and a lot of established photographers were closing and so I spent a year as a starving artist, and then had to get a real job. And that’s how I got into doing design, where I met my next mentor, a gentleman named Dave Larsen. He saw me as a designer that, head down when things weren’t going to get accomplished by my peers, I would jump in and make sure that we hit our deadlines, and he was the one that actually gave me the opportunity to move to Denver, he promoted me within that organization that was acquired by Equifax. And then the next step was EO and the mentors like Warren Rustand and having those people that continue to inspire you to tears.

Katty: Well said. EO for the audience is the Entrepreneurs Organization, a network of about 16,000 members entrepreneurs across the globe, and that’s how Keith and I know each other. We’re both members of EO, and have a lot of people, a lot of mentors in common. Warren Rustand is the gentleman that Keith just talked about. So, obviously, the influence of all of these incredible people has created an indelible impact on you, one that you carry with you still today. When and who kind of lit that spark of entrepreneurship for you? 

Keith: That’s a really good question. I don’t know. Actually, I do. I remember in seventh grade. The funny thing is it wasn’t really inspirational, it was my accounting teacher or some class that I had and I remember he explained a definition of an entrepreneur, and it was horrible. It was somebody that was going to have many failures before they have a success, probably have, you know, one or multiple bankruptcies. I mean he really described an entrepreneur as an atrocious choice to make in your life, and I remember sitting in that class and being like, “Huh, I think that’s me”. Going against the grain, not following the rules, and facing insurmountable odds with optimism. So it was sort of an adverse inspiration.

Katty: I love that. I absolutely love that. You can see this on my wall, it says “dwell in possibilities.” It’s my absolute favorite quote, and that’s what entrepreneurship is all about. There is a possibility out there so let’s go and do it.

Katty: I love that. At what point in your career after you were working and obviously studying photography, making the move to design and working for Dave Larsen. At what point did you say okay now I’m ready to start my own agency?

Keith: It was actually serendipity, so I had been doing some stuff as Zenman, as a freelancer, while I was working at Equifax, which is where I worked for Dave Larsen. And then they had moved me from California to Denver when the merger happened. Like with most acquisitions they within six months realize the redundancies that they’d acquired and they’d also moved us out here. So, I always had the goal that before I was 30 I wanted to be my own boss, to have my own business, to be an entrepreneur. And I actually was given a freeroll, I had a six-month runway, it was pre-September 11, the economy was great. Based on my management level, I had a half-year runway. I looked at that opportunity like once in a lifetime, I’m never going to be given this gift again. I took my severance package I tore up my resume, never to be edited or used again, and formed Zenman as official business.

Katty: It’s one thing though to go from being a solopreneur, and to running and creating one. Having employees, having that responsibility for other people, beyond just yourself. When did you make that transition?

Keith: That was a couple of years later. So for the first three years, it was just me, it was called Zenman because I was the Buddhist creative guy I was the Zenman. But then as we started adding employees and scaling, you’re absolutely right, two things happened; my stress level increased exponentially and my personal income decreased catastrophically. And it probably took five years to get back to where I was after adding that overhead and that did not alleviate the peaks and valleys that came with a service-based industry. 

We weren’t doing a lot of recurring revenue at the time, so each month it was eat what you kill, and it was feast or famine, many times. And I would even say past that, so that was eight years into the business. It was another five years before I joined EO, that I really learned how to be an entrepreneur. The first decade was stubbornness, willingness to work 100 plus hours a week, which led to, you know, illness and all sorts of issues. But it was actually learning how to run a business, learning how to be a leader, even learning what EBITA meant, which I didn’t know the first 10 years. These things are essential, but we don’t know them all right out of the bat. We weren’t taught those and you know photography school or, you know, wherever we go. 

Katty: I think you bring up a really good point, in terms of kind of what, what has been taught currently in art schools. For artists and creatives, as a whole really putting their practice and their expertise in the various programs that they use, you know, whether it be Adobe Creative Cloud or Figma or whatever it may be, but not to forget the business side of them because so many of them are solopreneurs and are running their own freelance business; to really have a good understanding of what the accounting side of it needs to be. Either to outsource it to an accountant and or do it themselves, whichever they want, but to really look at that business as a business. I think it’s really important to be able to have that full-scale picture of it.

Keith: It’s a really good point Katty because I learned the presentation skills and that’s one of the things I learned at Brooks was a well-put-together portfolio that’s perfectly mounted and everything is top-notch is going to get more jobs and better photography with a sloppy presentation. The one thing we didn’t learn was the business part of running a studio, photography business, freelance business. 

So for the first 15 years of my company or longer. I saw the business’s checking account like Monopoly money, it wasn’t real money to me until it came to me. I mean millions of dollars were wasted by not having that clarity and understanding and business education, which is essential. And I think you know the tables have turned, and now the most secure opportunity is to be your own boss to be an entrepreneur versus trusting your career into some other company hitching your wagon to that star and hoping that they not only are successful but that they continue to value your contribution and reciprocate that with job security.

Katty: Very very true and very well said thank you for that. Now you’ve recently transitioned out of your business. Is that correct? Am I saying that correctly? 

Keith: No, that’s correct. Yes, I sold Zenman to a SaaS company called Mblue in Latin America. It has been an amazing transition. I was really nervous. I know so many people sell their business and they lose their identity. They make a bunch of money and then they become miserable. I feel very very fortunate that it’s been a serendipitous partnership that maintains a legacy in the business and I’m helping them grow and accomplish their goals. I think the mindset of win-win, it wasn’t I’m tapping out the last day, it’s that I’m committed to it and that the people on the other side have the trust and respect to let us continue to run our practice as we do.

Katty: Fantastic. And obviously, I know this from having known you the past few years, you’ve embarked on this passion that is now your sole focus in your business, which is an incredibly beautiful journal that you’ve created for others to use, and I can see the experience for having put a great presentation together that you learned so many years ago, really manifests itself in the Oak Journal, it’s absolutely beautiful. Can you talk about what that spark was and why did you decide to go into this business?

Keith: Yes, it is a combination of two things, it is my Ikigai but I didn’t know it when I started down that journey. Ikigai is a Japanese term that means life’s purpose. But one of the things that I really wanted to do was stop trading my time for money. I realized when I had kids that time was the one finite resource we had. As an agency owner and a top paid creative, I make a lot of money per hour and it’s still not a good exchange. So, my goal was to come up with a product-based business that would fulfill my needs of financial independence without trading my time for money, and in finding the right product that’s how I came up with the Oak Journal. I wanted something that I could use my knowledge to create and do a better job than anybody that was currently doing this with the skills I built over the two decades of running Zenman. So being able to design something– I’ve designed many many books over the years, but being able to take the life experience, skills, you know even Warren Rustand’s 10 10 10 and weave that into a paint by numbers roadmap that anybody can use to live their best life has been transformational and it really made me want, with intention, transition out of the Zenman which was 100% my identity, it’s my nickname, it’s what people call me, to helping others and being a bodhisattva.

Katty: Fantastic. So, as a practice as a mindfulness practice and gratitude practice. Is that something that you were doing anyway before you put the journal together?

Keith: Yes, I’ve been meditating for 20 plus years and about 10 years ago I started practicing Transcendental Meditation, and it has had as big of an impact on me as the Entrepreneurs Organization has. Meditation is a superpower. If somebody doesn’t think that they have enough time in their day to meditate, you need meditation, more than anyone, and you will find if you start a simple practice, it gives you time in the day because you’re more productive, you’re more clear, you’re more creative, you’re more focused. I wish people would look at meditation like a free pill that would give them superpowers like that movie with Bradley Cooper, Limitless, you know, it’s not quite that but it’s pretty amazing how much, just having a 10-minute meditation can change your day.

Katty: I love that. Can you talk about that and creativity and where you see the through-line between the two because we talked about being quiet for a few minutes, that’s what we’re talking about here.

Keith: Yeah I mean that’s a really good question Katty thanks for asking. I mean the most amazing ideas if you look at, you know songwriters or inventors they happen in the shower or while they’re driving down the highway and the reason that is they’re not thinking about other thoughts, they’re not thinking about their problems, their mortgage their issues with their partner, they’re just washing their hair and at peace with their mind, their mind itself and so we’re able to come up with those really, really creative ideas. So I am intentional with creating those moments from meditation, to start my day to even having core hours where I turn off all devices not just my email, my phone is in airplane mode there’s no you know Twitter open. I don’t do that ever anyways, but you know there’s all distractions are turned off so you can focus on writing your book, working on that creative project, or whatever it is that needs to be accomplished. You can really get into those that state of theta brainwaves with intention. Willie Nelson actually does it by just driving his truck; he writes his best songs when he’s driving down the highway. So once he figured that out when he wants to be creative, gets in his truck and he starts driving. So there are all different ways you can get into that state.

Katty: Yeah it’s interesting because creativity doesn’t necessarily happen nine to five staring at a screen. It happens when you’re out in nature and happens when you’re just, you allow your mind to get creative. To go inward I think it’s just so important to be able to do that.

Keith: 100% I agree.

Katty: I’ve done meditation for years. I only can do it if it’s a guided meditation. I have not gotten to a place where I can do it on my own. But even in the guided practice, I find that so impactful and so helpful to be able to do that.

Keith: Yeah, I agree. Try TM it’s just a mantra I think that one will–And there’s nothing wrong with guided meditations. I still do those as well and I practice those with my boys, but I have struggled with contemplated meditations that weren’t guided until I found TM.

Katty: Okay, I will look into it. There’s also a couple of other friends who embark upon TM. You’re the third person I’m hearing this from, so I think maybe the universe is talking. So you’ve started your boys on meditation?

Keith: Yes, now we make that part of their day. In fact, when they were very very young, we had them in three different preschools before we found a school called Morningstar that was a yoga and meditation-based preschool. So the boys started every day with yoga, they did guided meditations. It was a very Eastern hippy Boulder-esque type of preschool, but it really resonated with our boys. Now, they don’t embrace it with the same joy that I do, but they understand the value of it. It’s almost like a joke in our house that we’ll all talk about the benefits of meditation and be like “I know Dad, you talk about this dad, I know that you wrote an article about this, dad.” So I’m hoping one day, they’ll listen with the same attentiveness that somebody to keynote does.

Katty: Fantastic. I know that the Oak Journal you just came out with a new version of it, can you talk a little bit about the differences between this and what you were doing? In addition to the different sizes, but what’s that creative process for you, because clearly you’re still a very creative person and you’ve just channeled that creativity into this.

Keith: Yeah, I love making things. So the main changes that we made, the biggest one is we move production to the US, and now it is being produced with environmentally friendly materials. The factory that we were using in China, didn’t have the same standards and so that was the biggest one to us to have something that was made with our core value of environmentally friendly alignment, and also, it helped with just production delays and shipping and everything we’re dealing with right now around the world. 

The other piece is, each week has a positive psychology exercise, and we had people that have been doing it for over a year and so they were repeating the same, let’s create our bucket list every nine weeks and so they were getting diminishing returns. So the next version is to 2.0, we’re going to make four versions total so that you can have 48 different positive psychology exercises. I’m sorry, 54 different exercises that you would do in a year in two weeks, and then you could repeat it. We’re also working on two other products. One is called the Sequoia, so that’s your 10-year journal you set your BHAG and your moonshot. And then you’re incrementally working towards that. With the series of 120 Oak Journals and then our passion project right now is the Acorn. So this is for children, and this is actually something that we’re intending just to give away. We’ll definitely print it and have them for sale. But anybody that wants an Acorn Journal anywhere on the planet will have a free.

Katty: How beautiful and I love all the tree references and all the nature references.

Keith: Thank you. Going back to our roots, beautiful. And thank you for connecting me to your resources for my journal too. You’ve been so gracious, I have to say that Keith, talking about mentorship, early on. You’ve just been so gracious with sharing your knowledge and all the trials and tribulations of bringing this journal to market and sharing that with me and with others who are interested in that. So definitely a mentor, so thank you for that.

Keith: Thank you very much Katty, I appreciate it. I truly believe all ships rise with the tide. And, the more we can help each other, it just benefits everyone. And I know more people having your book and your journal is going to help them. I think one of the things I’m blessed with here in Colorado is the creative community was very symbiotic. We do compete with people but at the same time, my competitors would reach out to me and say hey there’s jobs out of our league, this is more in your wheelhouse, could you take it. I think when you have that mindset of collaboration, then it’s reciprocated.

Katty: And it’s beautifully said because so many freelancers are so siloed and the importance of community can’t be overemphasized, to be part of that community, whether it’s Creative Mornings or AIGA or whatever it may be, but to find a community of other creatives to be able to collaborate with is so critical.

Keith: Yeah, you said it perfectly, not being on an island, not being in a silo. You know just leaning on somebody, I mean, EO was great during COVID. I don’t know how many people in our chapter wouldn’t have gotten their PPP, if it hadn’t been for other members that say hey I have this connection at a community branch we can help you, don’t worry about going through the big bank you’ve had for 20 years, you need to call Mary at Mbank and she’ll submit your proposal at three in the morning to get you taken care of. Mentorship, and also the peers that you just have, in a connected, trusting, and vulnerable way when people don’t have their guards up when they’re honest with what’s going on. It’s amazing how we come to each other’s aid. When we just raise our hand and say hey I need help. 

Katty: Yeah, very very true. It’s been an interesting year for sure. And we’re still in it, by all means, it’s not a done deal. What would you say is one of the biggest lessons that you’ve learned for yourself during this pandemic year and a half?

Keith: The importance of community and connection. You know I’ve seen other people that don’t have the network, that really struggled that sort of went inside and dealt with everything personally, versus just like we mentioned having that community that you can reach out to. I mean one of the blessings of EO is that it’s a global community. So, I took it as an opportunity because I could go have a coffee with a friend in Denver every day, to have a zoom call with a friend in Melbourne or you know just other ways to connect with people around the planet. I actually feel like, for me, it broadened my global connections, even though I wasn’t able to travel and I am chomping at the bit to go travel to meet these friends.

Katty: Yeah I agree 100% We did that on the family side. And I don’t know if I told you this when we saw each other last week, but since March 20th we started a family zoom, and we’ve had one every single Sunday since then. So March 20th of 2020, and my family is all over the world, nobody lives here in Los Angeles, so to be able to have this very intentional focused one-hour zoom call with one another. This is with grandparents and grandkids and aunts and uncles and the brothers and the sisters, that I think the max point we had 18 people on our zoom. And it still happens today, every Sunday at 10am. It’s the Douraghy family zoom call, and it’s similar to a forum exercise. So everything starts with an icebreaker: everybody talks about a win, everyone does a one-word open, and it’s been transformational because we’re actually learning things about each other that we wouldn’t otherwise because we’re not asking these very intentional questions of each other when we’re physically together. So it’s been phenomenal in terms of how close we’ve become as a family.

Keith: That is really cool, that’s such a cool gift. I think it’s also a perspective, right? I mean you could look at it that “hey I haven’t been able to be in the same room with these people.” But the flip side of that coin is you just created a tradition that hopefully will go on for generations. And we were blessed to have the technology to be able to do that, I mean even 10 years ago it would have been a different world we were in and I think so much more challenging to face this isolation.

Katty: Oh, I agree 100% 100% agree, and look, the future of work has changed. And without the technology that we have today wouldn’t have been possible to continue.

Katty: What is getting you excited and inspired these days?

Keith: You know what gets me excited is actually, I think, something that’s really messed up right now. And that’s the changes that I think are inevitable with social media. You know what’s coming out about algorithms intentionally presenting inflammatory content. I’m actually excited that there will be action taken to hold these people accountable. It’s going to turn the world on its head as far as advertising, e-commerce. But that’s already happening with iOS changes and privacy, which is not a bad thing. Personally, I am quite happy having the exact product that I want presented to me in a way that makes it easy to purchase it. But I am excited about the change that’s going to help remove the wedge that’s dividing this country apart because the truth of the matter is on 95% of the issues were exactly the same. And I think there are some toxic influences that are exasperating our divide, and I am for the first time in years, optimistic that we’re going to start taking that wedge out and coming back together.

Keith: Whatever we can do to make that happen.

Katty: Yes. And one final question for you, something to leave behind for our audience, especially those who are embarking on their creative career, and/or because of COVID have had to pivot their freelance business or if they’ve lost their jobs. What are some lessons learned that you want to leave them with in terms of determination to just continue, continue the task?

Keith: Two tools that I will leave one; I’m a big fan of Dr. Joe Dispenza, and he has a tool on manifesting what you want. So if you’re struggling right now, maybe you lost your job during COVID or your business failed or something. Set your intentions with a tool he created where you take a piece of paper out, you write emotions on one side and intentions on the other. So if your goal is a new job, what is the intention? I get to travel three months out of the year and see the world. I’m making enough money that I’m financially independent. What are all the intentions that you have? And then on the other side under the emotions, what are the feelings that you have? Actually, try to feel those emotions so you can manifest it. And that is a great tool. I love that tool but it is the first step. 

The second step is doing the work. The thing that I hate about the book The Secret is it’s all about having the right mindset and everything’s just gonna appear in your life. The mindset is critical. It’s essential, but it’s the first step, you’ve got to make continuous daily progress, you can’t just wish upon a star, that you’re going to have your dream job. What did you do today to actually accomplish that goal? What incremental progress, even if it was just five new connections on LinkedIn that you sent out. What was the incremental progress you made today towards living your best life?

Katty: Beautiful. Thank you, Keith, thank you for joining us here. Where can people find you and where can they find that your beautiful journal?

Keith: you can connect with me on social. Look for Zenman, you will find me or anything Oak Journal related, you will definitely find me and you can direct message me, you can even email me at if you have any questions.

Katty: Thank you. Before I let you go, I forgot to ask this, you also do a lot of sessions where you teach people how to journal and meditate and so forth. Correct?

Keith: Absolutely. Yep. I do it, I literally just got off one right before we started. I was doing one for EO Cape Town, but I also do them for individual forums, for companies and I have a masterclass that’s a six-week class people can do, it’s an Oak masterclass.

Keith: or Oak Journal. They all are pretty good at all the SEO interlinking web thing having owned an agency. So if you get to one of my properties you can find everything that you need and will guide you through that journey. 

The master class is a six-week intensive that we work on in small groups and then individually. And it’s a requirement I do a little bit of coaching but I’m really really particular with working with people that have the growth mindset that you know are going to be a good fit. So everybody has to do the masterclass first to make sure we’re both on the same path.

Katty: Got it.  I’ll put all the links in the show notes so that everybody knows how to find you and where to find you.


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