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Tropical MBA: Entrepreneurship & Founder Lifestyle

Latest episodes

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Mar 16, 2023 • 38min

TMBA 693: 5 Things We’ve Learnt From Speaking With 50 Business Owners

Today Dan and Ian reflect on some of the key observations they’ve taken away from calls with over 50 business owners during the launch of their implementation program ‘DC Scale’. And, this being the TMBA, there are 5 categories: ‘The $500K Stall’, ‘The Solo Recording Artist Mentality’, ‘Pulling Punches’, ‘Grade A at Hiring But Grade B at Managing’ and ‘The Cloak of Invisibility’: ‘Even today, when there are more people to follow then followers, and everybody's a brand … Most of these entrepreneurs are just not brands. And they really don't need to be. The vast majority of people we spoke with have a personal network, they are using channels like events, industry contacts, and referrals to bring in the key relationships that they need in their business. They're not necessarily using internet marketing funnels to bring in customers’. Dan and Ian also give their take on how and why the ‘Visionary vs Integrator’ definitions came about, and how useful they are, and share thoughts on the pros and cons of the ‘4 Day Work Week’.
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Mar 9, 2023 • 32min

TMBA 692: The Rewards and Sacrifices of Going Big

The story of Going touches on so many themes we’ve been following on this show for over a decade. Going’s original incarnation, ’Scott’s Cheap Flights’, came on the scene in 2013. And it started out mostly as a newsletter for digital nomads seeking the most cost effective ways to travel around the world, nerd out on ‘mistake fares’ by airlines, and other things of interest in the travel space. Today Going has over 60 employees and is a very substantial business, offering a range of options to its subscribers. On this week’s show Brian Kidwell talks to Dan about his personal journey from solopreneur to CEO of Going, the challenges of making that transition, the importance of seeking product market in whatever you’re working on, and finding time for ‘deep work’: “How can I have enough hours in the day to give the proper thinking, my best thinking, to the things that I need to work on? Because those things now have much more downstream impacts than before. It's like editing code, or responding to somebody - and I'm not trying to downplay them, because those are very important - but it was different for my brain … Now I can't work as long as I used to … I can't provide great thinking for 12 hours a day.”
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Mar 2, 2023 • 37min

TMBA 691: Making Things Incredibly Difficult and Pointlessly Complicated

TMBA has followed Tommy Griffith’s story for nearly a decade, watching his ‘dorky’ side-hustle teaching weekend SEO classes evolve into ClickMinded, a substantial online education portfolio. On today’s show Tommy talks to Dan about how ClickMinded has evolved further, with the help of a new CEO, to a white label documentation provider which turned over $2.3M last year. And he reflects on why he seems to have taken almost every ‘incredibly difficult and complicated option’ to get to where ClickMinded is today: “I think it was arrogance. We had this idea that we were an Ed tech company, that we were creating these online courses. I think there was also some sunk cost fallacy going on. I mean, we had 85 hours of HD videos, seven instructors, and some universities were using our courses … The product was great, we were super proud of it, and it took a lot of work to do. So the fact that people were saying, ‘Actually, can I just pay for all of these Google Docs’. It was a little hard to face that music.”
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Feb 23, 2023 • 52min

TMBA 690: Talking Content, Data Driven Decisions and Growth with Steph Smith

When starting a business or advancing your career, or even just seeking to increase your public profile, it’s a savvy move to build momentum through content, and specifically by focusing on a particular channel. Today’s guest is an expert at doing just that. Steph Smith is the author of ‘Doing Content Right’. She’s also the host of the a16z podcast and ‘The Sh*t You Don’t Learn in School’. Steph talks to Dan about the opportunities being a creator opens up, tips on how to choose the right channel for what you’re trying to achieve, and why being data driven is so fundamental to achieving growth: “If you are doing a good job with growth, data should rule the day. You should be able to clearly say, ‘here's an aspect of our funnel that we want to run a test on, because we believe it has this upside’. And you run the test …. I've gone on to other companies that were way less data driven. That's honestly something that I really struggle with because when you are in situations where you are having to kind of say, ‘hey, let's do this project, I think it'll maybe have some impact’. It's just not compelling to me. I think most things at a company should be pretty data driven”.
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Feb 16, 2023 • 50min

TMBA 689: Re-visiting Our Conversation with Seth Godin

Today's guest has been massively influential on Dan and Ian from the very start of their journey. Seth Godin is something of a legend in entrepreneurial circles, and he hardly needs an introduction.His books about marketing, creativity, building companies and personal development include Purple Cow, Meatball Sundae, The Dip, and Linchpin. They are frequent recommendations on this podcast and have long been shared among our listeners. In addition, Seth has founded an intensive four-week alternative online MBA called altMBA. He has also created several podcasts including the popular Startup School and Akimbo. Today's show features a wide-ranging interview, which touches on a variety of topics including Seth's history as a writer and podcaster, what the business world can offer society and much more.
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Feb 9, 2023 • 43min

TMBA 688: Mailbag: What Can Scorecards Do For You? And Equity Split Dilemmas

“This is an exciting podcast about traveling to tropical islands. And we're talking about employee scorecards.Why?” On this week’s show Dan and Ian share why they’ve introduced employee scorecards to their business, and how they’re helping establish more accountability, creativity and legibility in many different ways. They discuss the practicalities and principles of scorecards, the reasons they are so useful for both full-time staff and contractors, and why they are often welcomed by team members. They also give their thoughts in response to a listener email about one of the most frequently raised dilemmas in the startup world: how to handle equity splits when one person is doing the lion’s share of work while the other business partner still retains a full-time J-O-B.
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Feb 2, 2023 • 42min

TMBA 687: 5 Strategies To Double Your Business in 2023

As Dan recently reflected in the annual TMBA review, he and the Bossman saw their business almost double its revenue last year. On this week’s show Dan and Ian reflect on some simple principles or strategies that might help them and other business owners achieve the same in 2023. Now, as this is the TMBA podcast, they have to come in 5’s. Dems Da Rules. They include niching down to blow up, why playing with pricing dynamics can be so powerful, and the opportunities lifestyle businesses often miss by not defining clear strategies: ‘What is a strategy? It is a painful constraint about your mission in the marketplace, and how your entire operation is roped into that promise … (it’s saying) our strategy is going to be 100% organised around this deliverable. And because the whole organisation is organised around that, we can't be copied easily. That's the idea. We cannot be copied, we will sit alone in the marketplace.”
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Jan 26, 2023 • 31min

TMBA 686: Preparing To Take Time Away From Your Business

As Dan prepares to leave Barcelona after a month-long stay, this week’s show is all about being able to take time away from your business. Because that is, after all, one of the reasons many listeners to this show are creating lifestyle businesses - whether it’s for parental leave, to pursue a sport or hobby, or perhaps some very necessary mental health wellness. Both Sam Floy, founder of Cofruition, and Neil Callanan, founder of LooseGrip, have planned and executed successful sabbaticals. They share the reasons why, how they planned for it and some of the positive impacts it had on their businesses: “Maybe this is a male thing but you are less important than you think you are. And that was abundantly clear. I like to feel important, and I like to feel like my clients need to talk to me, and I need to set the direction for our team when working on a creative project or software thing. Turns out that's not actually true at all right? The team did great without me. Clients didn't feel a dip, really.”
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Jan 19, 2023 • 41min

TMBA 685: From Agency to COO to CEO - A Case Study From SPI

Agencies: creating them, the opportunities they offer, and some of the issues running them can create has been a long running theme on this show. Today Dan talks with Matt Gartland who ran a successful creative agency for eight years before partnering with one of his then clients, Pat Flynn, and eventually becoming CEO of Smart Passive Income (SPI). Matt discusses how he’s helping SPI develop further as a diverse media brand, ways of managing a growing team, and how he sees online communities evolving: “The primary value of these community based experiences is less the content, even though the content is important. It's more the network, the network of the people, the peer to peer interactions, the habits and experiences that you ritualize within these communities based on experiences. You need good people to be able to facilitate and foster those.”
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Jan 12, 2023 • 26min

TMBA 684: Personal Productivity vs. Business Productivity

Business processes and systems have been an emerging theme on this show recently, and today Dan reflects on why, and where they fit into the entrepreneurial journey. This often starts with personal growth through things like maximizing your health, reading, making connections, and maybe therapy. The second stage of advancing small businesses is frequently through different sorts of coaching. But, at some point, owners tend to hit roadblocks that can only be overcome by deploying systems rather than constantly fighting fires. Today’s guest, Aaron Lynn, has dug deep on this, at colleges, in businesses he’s founded and as a business systems consultant. He joins Dan to talk about the importance of quick wins as well as long term strategy, the difference between personal and business productivity systems, the importance of meeting cadence, and a whole lot more.

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