Connecting The Dots: Part 2

The 5 key influences that have jump-started my interest in entrepreneurship

Welcome to That Dude Denis, a newsletter about a dude who left the Bay Area and moved to Paris. The idea is to share my experiences as openly and transparently as possible as I try to become an entrepreneur, in the hopes that something may help you in some way. If you’re in Big Tech, startup-land, or just interested in entrepreneurship, this stuff’s for you.

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Happy New Year to all 111 of you That Dude Denis subscribers! 🎉

Last time, I gave you Part 1 of a two part series explaining how I’ve arrived at wanting to be an entrepreneur now at age 29 - it was all about my first 26 years of my life and how I lacked an entrepreneurial mindset and entrepreneurial influences for many years. This week, I’ll give you the 5 key influences that really jump-started my interest in entrepreneurship.

Without further ado, here’s your first dose of That Dude Denis for the year, featuring a podcast, a book, one of my former Apple co-workers, and two French dudes, one of whom I’ve never actually even met in person. Enjoy!

How I Built This

Ah, NPR. For those of you non-Americans, NPR stands for National Public Radio. Everyone used to listen to it on the radio, back in the days before iPhones, iPods, and even CDs. My personal relationship with NPR goes back to my kid days when I’d listen to “Car Talk” on the car radio on my way to Kung Fu practice with my dad (yep I did Kung Fu, don’t even pretend to be surprised). Nowadays, I don’t know if anyone still listens to NPR on the radio, but they’ve now become a massive producer of content across a number of popular podcasts, including Fresh Air, Planet Money, and my favorite...How I Built This (HIBT).

HIBT is a podcast about successful entrepreneurs and their stories. Each episode is centered around a different entrepreneur - some are super well-known, like Joe Gebbia of Airbnb or Richard Branson of Virgin, while some you’ve probably never heard of, like Sarah Kauss of S’well or Yvon Chouinard of Patagonia, but whose stories are just as insightful and inspiring.

It sounds weird, but back when I first discovered HIBT, listening to each episode gave me a huge rush of energy - it was like injecting my brain with adrenaline, causing me to get all giddy with excitement and setting off idea fireworks inside my head. It was one of the first times I can remember feeling this way, and as a result, my post-episode ritual was to literally tell everyone about it. 😬

Why did I love HIBT so much?

1. It made successful entrepreneurs seem down-to-earth, easy to relate to, and all so normal. I mean, if all Gary Erickson needed was a kitchen and some simple materials from the grocery store to create the first Clif Bar, I could theoretically do it too, right? After all, I, too, have a kitchen…this was an exciting revelation to me. And because they all had different origin stories, it was also easy to find elements that I could easily relate to and draw inspiration from. Some had previous industry knowledge (like the Warby Parker founders), while others started from zero (like Mei Xu of Chesapeake Bay Candle). Some first developed their startup on weekends and evenings while working their full time job, while others literally quit their jobs before even starting to brainstorm what to work on (Melissa & Doug).

2. It introduced me to a new way of approaching projects that centered around short-term versus long-term goals. Instead of taking a long-term view, trying to plan out what could and might happen in the future, most of the entrepreneurs opted for a very short-term view, taking things literally one step at a time and re-evaluating after each step whether to take another or not, and if so, in what direction. It was an action-first philosophy that starkly contrasted with the planning/preparation-first philosophy I was used to approaching problems with (common for an engineer, I think).

Jason, my first entrepreneurial friend

HIBT inspired me with stories of successful entrepreneurs and their humble beginnings, but Jason was the first entrepreneurial-minded friend I ever had.

Jason became a colleague of mine at Apple a year before I left, working closely with me on a new Apple product, with him in charge of the code and the wires and me on the non-code and non-wire stuff (yeah…that’s a really rough approximation). He was almost 30, which may seem irrelevant, except for the fact that he’d always dreamt of running his own business by the time he was 30. We both weren’t that excited about our jobs at the time - I could already see my life in France getting closer and closer each day, and Jason was looking for opportunities to start his own business. We were both mentally free to put our energy into something.

Jason was the one who came to me first with an idea: a machine that makes custom-fitting clothes to reduce waste. One day he was asking me if I’d be interested in hearing about it, and the next day we were setting up Slack channels, sharing notes in Notion, and adding to-do items in Trello. 🤯 All 3 were tools I had never even heard of before.

What were some of my major takeaways from working with Jason?

1. Passion, energy, and enthusiasm is infectious. He brought an energy and an excitement about the project that I had rarely encountered before, and that excitement rubbed off on me, so much so that I even considered postponing our Paris plans to see what the next few months of the project might bring. I remember thinking to myself: ok, so this is what an entrepreneur is like…

2. It’s OK if you’re not a subject matter expert, as long as you’re proactive about getting the information you need. Did either of us know anything about making clothes? Nope. The last time I had ever used a sewing machine was in middle school, when I had made an apron in my home economics class (this is what we teach our kids in America, apparently). But that didn’t stop Jason from meeting fashion industry experts, attending conferences, and getting hands-on with his sewing machine to fill in the knowledge gaps.

3. Less talk, more action. Like many of the entrepreneurs featured on HIBT, Jason was all about taking tangible steps to move forward as opposed to planning far in advance. Sure, there was still some planning, but for the most part we kept our focus on the immediate next steps right in front of us, continuously achieving small wins that then helped fuel our motivation.

The Four Hour Workweek (4HWW)

With HIBT episodes still saved on my phone and with memories of working with Jason still fresh in my mind, we hopped over to Paris, where I started a new 9 to 5 job at Possible Future. Almost a year passed before I finally decided to pick up reading again, luckily landing on a book called The Four Hour Workweek.

I admit, the dude is super extreme (he’s a kickboxing champion, breakdancing champion, and holds a Guinness World Record for tango spins under a minute 🤯), which understandably causes some people to dismiss his message as unrealistic and unachievable for the average person.

However, the book had an opposite effect on me. With it, Tim Ferriss captured my imagination and completely turned my view of what life could be on its head.

My pre-4HWW self thought that life generally looked like this:

• 1/ Work 40 hours a week

• 2/ Have one or two vacations per year

• 3/ Earn and save money until you retire

• 4/ Retire and finally reap the rewards of a life spent working

Tim takes this popular paradigm and breaks it into tiny little pieces by presenting an alternative approach to living based on the premise that we can and should enjoy life to the maximum during our prime living years, as opposed to waiting until we’re retired and way past our prime to do so.

How, you ask? Tim’s answer: free yourself from the physical and temporal constraints of your typical 9 to 5 job by developing your own sources of recurring revenue that allow you to dictate when, where, and how you work. Once that achievement has been successfully unlocked, you can do crazy sounding things like take mini-retirements every year, spending 3 months living anywhere you want in the world while continuing to make money by managing your businesses for just a few hours a week.

“$1,000,000 in the bank isn't the fantasy. The fantasy is the lifestyle of complete freedom it supposedly allows.”

- Tim Ferriss in The Four Hour Workweek

What were the most important learnings I gleaned from Tim Ferriss and 4HWW?

1. Having a 9 to 5 job until retirement has significant downsides. It helped me realize very clearly the limitations and constraints of having a standard 9 to 5 job and motivated me to actively consider an alternative approach towards life planning and life goals.

2. An entrepreneur can have different ambitions and goals. Being an entrepreneur doesn’t necessarily mean starting a hyper-growth company in the hopes that you’ll raise money, make it big, and become a unicorn. It can also mean creating small businesses, solopreneur-type products and services that generate enough recurring revenue in an semi-automated way to give you the financial freedom to live life the way you want to. There’s absolutely nothing wrong with that.

Clément, the just do it guy

I finished reading 4HWW at the beginning of 2020, and so not surprisingly, I wasn’t super excited by the prospect of another year of consulting work at Possible Future. I was slowly getting more interested in entrepreneurship and startup stuff, and luckily for me, an opportunity opened up in the startup studio*, which was in the beginning stages of a restructuring. In the driver’s seat was a guy named Clément, who was hired to breath new life into this small but important part of the business. Great chance to turn down the consulting stuff, and turn up the startup stuff, I said to myself, and with that, I started working with Clément.

*What is the startup studio?

Our startup studio is a structure built to accompany founders to validate, develop, and launch startups by leveraging our strong network of corporate partners and our diverse set of in-house skills and expertise, and by providing financial support when needed.

It was another great chance to work with someone full of energy and enthusiasm, and in this case someone with a background in entrepreneurship and a real interest in the startup world. He not only was the proud owner of a poké shop in Paris, but he also came through a prestigious French entrepreneurship Masters program, so he had both formal and experiential training in the subject matter already.

But the most important thing Clément taught me wasn’t a specific skill or knowledge, but rather an attitude. Do first, ask forgiveness later. PF is a relatively small company, but like any company, it still has its fair share of bureaucratic red tape and workplace politics which clashed at times with our desire to move quickly and make decisions. Instead of asking for permission and playing the waiting game, Clément wasn’t afraid to simply say what he thought and do what he thought was right.

Sure, he made mistakes. All of us do. Sure, he may have unintentionally offended people from time to time, but that’s part of what entrepreneurship is as well - you need to have thick enough skin to push the boundaries, knowing that you may accidentally push too far and suffer the consequences. But you can’t be afraid to step on a few toes, hurt some feelings, and bend some rules if you’re trying to get somewhere. That’s what I learned from Clément.

Yoann, the LinkedIn master

As part of my startup studio role, one of our tasks was to create a sort of founder’s toolbox, a comprehensive toolkit of resources and guides to help the first time founder easily navigate the early stages of startup creation. During this process, I came across a partially finished Notion directory about company building that had been created and shared by a dude named Yoann, who at the time was Chief Marketing Officer at Comet (he has since quit to run his own paid personal finance newsletter, Snowball).

It’s funny. I’ve actually never met him in person and have only ever spoke to him once by call so I can’t say much about his personality here (other than that he’s a super nice and helpful guy), but since connecting with him in April of 2019, he’s still somehow made a significant impact on me, through only his LinkedIn posts. Seems hard to believe but it’s true.

So in what important ways has Yoann influenced me via his LI account?

1. He showed me how to build an audience by being consistent and by providing value. This may seem simple and obvious, but before meeting Yoann, I had never actually thought about how to build an audience, or how it could be useful. I’ve learned a lot more since then, but it was through Yoann’s weekly “Monday gifts”, “Sunday side projects”, and “Wednesday tips” posts that I first saw how consistently posting high value content could be used to build an engaged audience. The rapid success of Snowball can be at least partially explained by the reputation he had already built up through his LinkedIn posts. 🧠

2. He introduced me to the world of no-code. Ah yes, one of my favorite subjects of the moment! The amazing world of no-code tools allows non-developers like you and me to do amazing things, like create functional mobile apps and whip up beautiful websites, enabling us to quickly and easily validate, develop, and launch our ideas. Every week Yoann would drop another awesome tool, tip, or trick onto my newsfeed to check out, like no-code app-building tool Glide, which he had used to create a simple “IMDB of newsletters” app.

3. He gave me one of my first examples of how to build in public*. The build-in-public movement has captivated me more over the last few months (it’s one of the major reasons for this newsletter), but I have Yoann to thank for informally introducing me to the concept, first by publicly sharing internal Comet documents like their organizational chart and their decision-making process, and then later by breaking down and explaining how and why he built Snowball with complete transparency - if you check his LinkedIn, he consistently shares his revenue and subscriber count for everyone to see! If you really want to get a sense for how open and transparent Yoann is, just take a peek at his year end review articles: 2019, 2020. 😉

*What is "building in public”?

“Unlike a lot of startup jargon that is confusing to the uninitiated, building in public is pretty much exactly what it sounds like. When a startup builds a product or service in public, they allow people to see their building process from the start.”

- Entrepreneur.com

So there you have it, the five biggest influences in my entrepreneurial life so far: a podcast, a book, and three real entrepreneurs who have each taught me and inspired me in important ways. Together, they have molded and shaped my interests, my views of entrepreneurship, and how I see my future.

I know this post is already a bit long, but if work hasn’t fully picked up yet and you have a bit of extra time this week, you should check out some of the stuff linked above if it interests you! There’s some great content to be found on the other side of some of those links. 🤩

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Thanks to KT for editing, and my noise-cancelling headphones for helping me focus while I wrote this. 

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What’s coming up next? 

You’ll actually hear from me a lot sooner than usual (don’t get used to it) - there’s a post that I’ve already started writing that I’ll be sending out at the end of this week that talks about something fresh, something new. Because yes, finally, we’ve reached present day and I can start sharing stuff about what I’m actually up to! 🙌

Again, if there’s something you want to learn more about, please leave a comment or write me. I’ll give you a quick response or maybe even dedicate an issue to it if I think it’ll be helpful to other readers.

Amazed that you’re still reading, but I appreciate it greatly! 🙏 If you enjoyed this post, please subscribe below if you haven’t already.

Hope 2021 is off to a great start!

That Dude Denis

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Wow! You’ve just finished the third issue of That Dude Denis, a newsletter about a dude who left the Bay Area and moved to Paris. The idea is to share my experiences as openly and transparently as possible as I try to become an entrepreneur, in the hopes that something may help you in some way. If you haven’t already, please subscribe here: