In this six‑question, seven‑minute interview, Professor Pete Alexander talks with Samuel (Sam) Cook, co‑founder and CEO of SanityDesk and founder of James Cooke Media. Sam describes his companies as all‑in‑one platforms that help experts, authors, and solopreneurs build, market, and manage their businesses online. He frames software development as "digital real estate," emphasizing that unlike physical land, the only limit is imagination and market demand. Sam argues that real business wisdom comes from experience and mentorship rather than formal MBA or engineering degrees, noting that imposter syndrome is universal but can be mitigated by learning from seasoned mentors. He stresses "confident humility" – accepting that leaders will never have all the answers, embracing imperfection, and staying open to learning from teams, customers, investors, and board members. Sam highlights the strategic advantage of having a board of directors, sharing his own recent experience inviting Tony Orlando to join his board, and recommends that even non‑funded founders consider forming a board for accountability and mentorship. He recounts his first paid job as a busboy at a pizza restaurant, describing how the pride in meticulous, unseen work taught him discipline, intrinsic motivation, and a habit of constant improvement that later served him in the Army and entrepreneurship. The episode closes with Sam directing listeners to sanitydesk.com for a free trial and consulting, and to jamescookmedia.com for storytelling training, while Pete promotes the podcast’s channels.
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This is Professor Pete Alexander with the Winning at Business and Life podcast, where business leaders share their insights. It is 6 questions in 7 minutes because successful business leaders are busy and rarely have more time to spare. So let's get to it. Question number 1: In a few sentences, please tell me who you are and what you do.
My name is Sam Cooke. I'm the co-founder and CEO of SanityDesk, which is an all-in-one software platform that helps experts, authors, solopreneurs build, grow, and manage your business all in one place. And, uh, yeah, and I'm also the founder of James Cooke Media, which is a media company that also helps experts and authors market themselves. So That's my business career.
Sam, it's great to have you on the show. Question number 2: What's the best thing about working in your industry?
The thing I love about technology is, uh, in the world of technology, you have limitless potential, uh, in terms of what you can imagine and build is really bound by your imagination. If, if you think about Software development is like real estate, but digital. And the constraint in the physical world of real estate is there's only so much land. There's no such constraints in the software industry. So what you can construct is really just bounded by, you know, what you can literally come up with as a, as a, as a developer, as a business owner, product owner. And your engineers, uh, matched with what people want, right? So obviously you're bounded by the market, which is the, the true constraint of software is the, the people rather than the, than the land out there that is in physical development. But I like to think of software development, product development, as real estate online. And, um, there, there's just a great, um, uh creativity mixed with science. So the art and science of software development is what I love about.
No, it's a great description, and I love the metaphor between the software development and the real estate market. So it was a great description. Thank you. Question number 3: I have a fictitious book with all the answers for business. What chapter would you think most companies should read?
So, all the answers for business, um, I would say I would start with the last chapter, which is a summary of everything that you should have learned in the book. And for me, one of the things about business is you can go get an MBA in business, but ultimately, experience is everything. And as a business owner, You can read a book, you can read a course on business, but at the end of the day, it all comes down to your experience. I didn't study business and I have no business according to my educational pedigree of running a tech startup. I didn't study engineering. I didn't study business at school. I was a history teacher. But what I've learned through the process of running a business is It's all about experience and you're always going to have imposter syndrome. You're always going to feel like you don't belong, that you're not ready. But the best book you can get really is mentors and getting people who've been there before, who've lived the journey that you're on and listening to them. I love books. I love to read books. I'm a big fan of books as a history major, but ultimately the best book is your own experience, your own If I would have known then what I know now, I never would have done what I've done. If I would have known the financial reality, the risks, the pain, never would have started. And there's a certain quality to your naivete as a business owner that is beautiful. And never let anyone tell you that something can't be done. Find mentors who believe in you and get the advice you need. And the books, I don't think are that important actually.
That's so well put. Thank you so much. And question number 4, which likely falls into what you just answered: other than the generic work harder, have a great attitude, and care for customers, what advice or insight would you give to other business leaders?
Um, really what I found in business is, uh, I think it goes to the, the point that I made before is, um, Understanding that you're never going to be right, you never have all the answers, is critical. And there's a certain humility to great leadership that I've observed in my career as an Army officer and as a business owner is understanding the limits of what you know. About your market, about your customers, about the technology that you're dealing with. And I think the hardest thing for a business owner to come to terms with at the beginning is the limits of what they can achieve and becoming comfortable with never having the right answer, but always looking for better answers. And once you are okay with the fact that you're never gonna have all the answers, you're never gonna have a perfect product, You're never going to have the perfect team. You're never going to have the perfect balance sheet, the perfect leadership style. There's a certain liberation in getting rid of your need to be perfect. Because if you're a perfectionist as a business owner, you're not going to last. You have to be always okay with being wrong because the market is the ultimate judge. Humility check and always being open to learning from your team, from the customers, from investors, from board members. And everyone that you never thought you could learn anything from is going to be your best teacher. So I think humility as a business leader is the most important quality, which is hard because to go into business, you have to be a bit bold and pigheaded and stubborn and stupid at the same time. So confident humility.
I like that, confident humility. It's perfectly said. Question number 5: Other than— what other business leader like yourself would you like to acknowledge and invite to be on my podcast?
Well, I would say that, you know, one of the best The best people that I've learned from recently is a board member. His name is Tony Orlando. He would be a fantastic guest. The reason I named Tony is Tony was considering investing in my company and I decided to, at the advice of one of my investors, invite him onto our board. Even though he had not yet invested in my company and still hasn't, but plans to, creating a board with Tony, who has a lot of experience as a board member, who really sold me or opened my eyes to the value of a board, was fantastic. And as a business owner, your dream is to not have a boss. But ultimately, as you mature and you run a startup, you raise money, investors rightly demand that you have some accountability, which the board provides. And I would say that even if you are not considering raising money, you never want to have investors, that a lot of business owners would benefit from forming a board of directors. I'm forming a board of directors for my media company, even though I don't want investors there, just because I believe that What Tony showed me about the power of a good board, a good mentor who's holding you accountable as a business owner, you as a business owner answer to your board. Now, of course, if you're the majority shareholder, you can fire and reshape your board as you like, but still having a board that, that is accountable, that you're accountable to, I think is one of the best lessons I've learned recently raising money as a tech startup founder. And I think Tony's a fantastic person for the audience to hear from about the power of aboard leadership mentorship that is way more valuable than any investor could be for their money is the advice that you get. Saved me so many mistakes, wrong paths already. And I think I couldn't recommend a better guest to educate your audience on something maybe a lot of business owners haven't considered, which is the power of a board.
Perfect. Well, thank you so much. I'll reach out to Tony. I really appreciate that referral. And our final question, question number 6, please tell me about your first job.
So my first job was I was a busboy at a pizza joint in Lake Charles, Louisiana called Mr. Gatti's. I was 16 years old. I quit the sports team. I was a football player and baseball player my freshman year. Quit my sporting career and took up a job my sophomore and junior year of college. And it was, it was a Mr. Gatti's. And I remember cleaning tables and our closing duties were to clean the bathroom and to clean the dining room and the back office that no customers would even see. And I remember taking a perverse pride in making everything as good as I could make it from a cleanliness perspective to the point where it was way past the standards that were expected of my boss. Not because I thought the boss would even check or care, but because it was just, uh, it was just a personal challenge. And it was this whole, um, process of always being better and this, this constant improvement. And the thing I have always loved about all of my jobs, and I think everyone gets something from a job, is something that continually challenges them where you have intrinsic pride in your work and you don't need extrinsic acknowledgement, um, you know, validation from your, from your boss and being able to find your own little island of, um, Zen or, uh, you know, uh, constant improvement or, um, personal development in a job that wasn't something I wanted to do the rest of my life. Cleaning was a great lesson early on. And I definitely took that to the Army where I went to West Point and became a cadet there and then graduated and became an Army officer. My first real career was the military. I started at 18 as a cadet. But my first job where I got paid money was actually Mr. Gatti's. And I think it really set me up. It certainly was humbling. But also taught me the value of hard work on things that no one really cared about, which was, you know, keeping the restaurant clean and, you know, doing my job. So that was a lot of fun and something I think I'll always draw from.
That's a great story. Thank you so much. And Sam, thank you so much for being on the show. How could people find you?
Well, there's two ways. If you are a business owner and would like to get help setting up your entire website, your marketing automation, your support desk, all in one place, you can go to sanitydesk.com. You can sign up for a free trial of our software and get a free website consultation from me or a member of my team to actually spend an hour or 3 hours with me if you go through the whole process of setting up your business online with our software. And then the other place you can go is jamescookmedia.com. It's a company named after my little brother who passed away. Who is a— was a true Renaissance man, loved books, loved knowledge. And that's where I started my business career as an agency owner, helping small business owners grow their business online. And I was particularly passionate about, and still am, and that agency still exists to help authors, experts, podcast hosts like you, Pete Alexander, and others build, manage, and grow their business on one place, one software platform that I always wish would have existed, which never did for me or my clients, but now does in SanityDesk, the software that James Scoot Media built and then spun off into a tech startup, which is now has 7 angel investors and growing quite quickly, SanityDesk. So those are two websites, jamescootmedia.com, where you can sign up for free training on storytelling. And sanitydesk.com where you can have a free trial with a member of my team to help you set up your entire business in one place online.
Wonderful. This is Professor Pete Alexander with the Winning at Business and Life podcast. For more insights and ideas, please go to LinkedIn, YouTube, Facebook, or iTunes and search for the Winning at Business and Life podcast. Thanks for listening.
