Tropical MBA: Entrepreneurship & Founder Lifestyle

On today’s show Dan and Ian are reaching into the mailbag to reflect on some topics that listeners have asked about. These include an update on the incredible response to our upcoming DCBKK, things to consider when thinking about business models, and how to manage your net worth without hurting your brain: “I have been guilty in the past of overcomplicating my financial process with too many credit cards, too many bank accounts, too many clever tax manoeuvres, and I would have been much better off to keep it super, super simple’.

Today’s show challenges bootstrapped entrepreneurs to think about lessons they can draw from high-income private equity funded business, especially about structured forward planning and accountancy. But it also covers what lessons PE funded companies could learn from the other side of the tracks. This week’s guest is Jason Long, a valued member of the DC community, well known for being always open to sharing the highs and lows of his long experience of founding agencies, creating Software as a Service businesses and, most recently, from accepting a job as a ‘turnaround CEO’ for a private equity group. He talks to Dan about how the devastating effects on his agency of the 2008 financial crash caused him to diversify his portfolio, and the pros and cons of that decision. Plus why working with a multimillion PE firm has enhanced his experience both as a leader and entrepreneur: “This is a team that had been passed from CEO to CEO, from leader to leader, who just had failed them over and over and over again .. And so when I came in, I said, ‘I’m not gonna I'm not gonna fire anybody’ .. And I brought in a lot of methods to make sure that there was transparency with the top level all the way down to the frontline workers .. so everybody felt like they were knowledgeable about where the company was going. And I felt like that made a huge difference in the trust”.

Lots of entrepreneurs and listeners to this show are inspired to create ‘The 4-Hour Workweek’ type businesses by founding e-commerce stores and agencies, creating money and value entirely online. Today’s guest, Alex Pantich, has chosen a different path with the business he co-founded. Upshift provides hospitality venues with vetted temporary W-2 hourly workers who are able post online the days and hours they are available for work. Alex talks to Dan about how this double-sided marketplace works, the equity share scheme Upshift deploys, and why he thinks so many entrepreneurs are missing out by not considering blue-collar, location dependent opportunities: “When you're getting online and into E-commerce, you're competing with your peers. If you go into the real world, you're competing with baby boomers. Are you telling me the baby boomer who doesn't know email is going to beat you at any sort of innovative business game? They're not. I prefer going into areas where I see tonnes of opportunity and not as much competition”.

This week’s show is kinda a de-brief of our recent in-person event in Playa Del Carmen, Mexico. Dan chats Jeff Pecaro, who has worked with us for nearly a decade, and continues to do an amazing job helping our speakers deliver the kind of presentations that our attendees tell us they want to hear: “It’s not a traditional business conference audience in the sense that they don't want to hear your theories, and they don't want to hear your grand success story, they're looking for the things that they can take, and give to their team on Monday morning to help them grow. So it's really much more of a community of peers than it is a captive audience. And I think that's a big adjustment for a lot of our speakers. Expect to hear: thoughts on PDC as a venue, some common themes that we’re seeing in our community as its revenue aspirations continue to grow, and some takeaways from the awesome on-stage presentations.

Have you ever wanted to get a regular review process going but just never get round to it because it seems so overwhelming? This show is for you. Dr Anthony Gustin, chiropractor, e-commerce entrepreneur and farmer, has been honing his annual review system for over 10 years. It’s available, completely free, online and has greatly influenced people like former AppSumo CEO, and recent TMBA guest Ayman Al-Abdullah. So, why not click on the link and follow along as Dan talks to Anthony about the six steps he suggests for those struggling with identifying and achieving goals in both business and personal lives. “A year is such a long time. It goes by like that. When you look back at what you can get done in your day to day, it seems like you're not making any progress but you look back on the year, it's insane how much you can get done”.

One of the themes of this show has always been ‘learning by doing’, and evolving your businesses based on that. But what about when your circumstances change and, through necessity, that places different pressures on what you need to achieve? Dan first met Dana Lindahl a decade ago when Dana was just starting out as a 21 year old copywriter, creating a decent amount for living in Bali. In today’s episode he shares why feedback from that resulted in him starting Legendary Leadgen, plus how a move back to the US led him into the podcast industry with Legendary Podcasts, which has seen such rapid growth that it quickly showed up some of his personal challenges: “I just had this sort of lifestyle agency, that was a good job for me, and I was happy there. And then all of a sudden, I was thrust into this situation where I needed to employ a level of skills that I hadn't quite developed And that's what I'm spending a lot of my time this year doing”.

On this week’s show Jeff Fruhwirth talks to Dan about how a failed foray into e-commerce, and a change in personal circumstances, caused him to pivot into real estate investing with little capital or experience. Today he has a portfolio of multi-unit buildings, which he’s expanded by learning about the hidden potential within different sorts of properties: “One of the best ways to make money is to kind of take on deals that no one else wants to touch. I looked at a building last summer that had been hanging on the market for quite a while. And the main issue was .. there was a five unit apartment building and a two bedroom house, but they were on the same tax lot and share the same water tap. So there was plenty of money in there, as long as you are willing to pay to dig up the water and sewer line, and then pay the $13,000 to the water utility to get the water metres separated … then you could sell off the house, you could fix up the apartments, and functionally double the rent”. Jeff also shares some inside stories and insights from the very first DSki, which took place in Steamboat Springs, Colorado.

This week Dan and Ian share updates about progress at ‘Dynamite Jobs’. Drawing on some sage advice from recent guest Ayman Al-Abdullah, they’ve been focussing on the ‘P’s that really matter, namely breaking through plateaus by building strong foundations through ‘product, promotion and process’. The idea being that will enable them to move on to the next stage in their business, from ‘player to coach’: “One of the points that Ayman made is, ‘Look, you are the last star player, you're ever going to get on a rookie contract’, everyone else is going to work less hard than you, is going to care less, and is going to demand more money”… So when you're ready to pick up the clipboard, you have to have a rock solid legacy in place in terms of product, promotion, process and people … And now all of a sudden, we're not jumping the gun. I want to flag this up because I see a lot of people trying to get to that mid eight figure seven figure business by jumping the gun on bringing in the executives that are kind of doomed to failure, because there's no clarity on how the business will grow”. And stay tuned to the end to hear Dan and Ian’s thoughts about resume gaps and ways to fill them.

The last time Allen Walton was on the show he talked about the origins of his e-commerce business SpyGuy grew out of a difficult period when he was living in his parents’ basement struggling to make a living. Today Allen talks to Dan about some of the challenges he’s had which, despite the considerable success, has caused him to consider if it’s time to re-orientate what he’s doing and focus more on his new venture FlyGuy: “Spy Guy is a hard business to run. Like a lot of e-commerce businesses we've been facing supply chain problems, shipping shortages, our costs have really gone up … And I think about Tony Hsieh’s book ‘Delivering Happiness’, he talks about poker playing, and how you could sit at a table and you might just keep losing, losing, losing against the people you're playing with. One of the best things you might do is just get up and move over to another table. You might find out that you're playing way better there. And I kind of feel like that might be the case for me”. And, later in the show, Allen gamely agrees to play our favorite fun challenge: ‘Donate A Business Idea’.

One of the biggest challenges we discuss on the show is how to take businesses over the “five figure” hurdle. Today’s guest Ayman Al-Abdullah has done that in his time as former CEO at AppSumo, and he shares his major takes on achieving that with Dan. “You're essentially crafting your rock band. What more important job than who I'm hanging out with on a daily basis and hanging in the tour van, I think the most important job of the CEO is: ‘Who is in the van?”