Make your next bet small and unpredictable
Plan Your Next #88
👋 Good morning from Los Angeles! I'm Nate Kadlac, and this is #88 of Plan Your Next. A Sunday newsletter that connects design, creativity, and how you prepare for your next thing. Thank you to all 600+ people who have joined Plan Your Next!
💡 What’s new?
🎁 SuperHi announced an incredible deal this year. Buy one annual subscription, and gift one. So I did the only responsible thing I could think of—I bought one, and I'd like to gift one! I’ll randomly select someone who replies to the question, “What’s one design goal you have for 2022?” Respond by Monday night at 6PM ET.
👯♂️ I pre-launched Slide Decks with Style using Figma on Friday. I’m floored by the response so far, mainly because it’s only about 40% done. If you have ever needed to tell your story to investors, friends, business partners, or your team, I think Figma is a great way to do this. Why? Because it blends both the capabilities of a high-fidelity design program with the collaboration and accessibility you get with Google Slides.
☕️ The top link in last week’s letter was the electric kettle. You all sure love your coffee! (I regularly make my own cold brew using the OXO Good Grips)
Good morning from Los Angeles!
Everywhere I look, it seems like someone is working on a big idea. It’s an attractive thought, and something I wanted to do myself for a long time.
Boostrap a product, find product-market fit, raise some capital, work with investors, hire an excellent team, exit, celebrate, then who knows?
But that, “who knows,” is a critical point. What does that mean exactly? What was I actually looking for?
I don’t think I had a great answer back then. Building a company takes 5-10+ years, and incubating an idea into a fully formed product with sustainable revenue, selling it successfully, and living that sweet sweet life, is not a linear path.
You could say I failed at that, never quite figuring out product-market fit for some of the projects I was involved with.
Up until about 18 months ago, I avoided making small bets because it was difficult to see how it could blossom into something big enough to be sustainable. Selling a font or an icon for $5-10? How would that make a dent in my living expenses? And maybe more importantly, would I want to be the guy known for selling digital doodads vs building something bigger?
Hidden in that chaos, was a very important flaw.
The unpredictable nature of placing bets
Very few of us truly like unpredictability. It’s why so many people opt for a W-2, even though it can be unpredictable as billing as a 1099 contractor.
My flaw was not embracing the upside and random unpredictability.
A $5-10 digital doodad would have taken me less than a day’s work. On its own, it’s small, unpredictable, and volatile. But that’s exactly what making a small bet should look and feel like. Unpredictable, but with unlimited upside.
Then make as many of these unpredictable, small bets.
This isn’t an uncommon practice when you think about bets placed by venture capitalists, music labels, or film studios. The entire strategy is to spread out their capital across a number of investments, hoping one or two hit big.
At the creator level, small bets can feel extremely small. Sahil Lavingia built Gumroad on the back of an icon he created, but couldn’t find a way to sell it online very easily. His small bet turned into something much greater, and that’s the unique unpredictability of making small bets. The risk is low, but the upside isn’t.
Building my portfolio of small bets
However resistant I was, it was a total mistake.
When I invest in stocks or crypto, I have placed a number of small bets across a gamut of tokens, hoping that this stochastic process rewards me down the road, randomly.
Like investing in art, musicians, or companies, I plan to build my portfolio of small bets starting with Slide Decks with Style. It took me a couple of days to shoot and edit the first few videos, and another day to put together a landing page.
Just like I don’t place too much money in one stock, I don't plan to run everything I have at these two courses, but I do plan to build out a number of small products as a way to start placing many small bets going forward.
What’s the smallest bet you could make on yourself?
⚡️ Two creative hits for next week
Gumroad just launched a beautiful brand refresh and all-around redesign of their site. Big fan of the personality and style being displayed, and the unique 100% width logo at the top. What do you think?
A new font by Dan Cederholm called Cartridge
Inspired by old video games, Cartridge is a display typeface (meant for H1s or large headers) that conjures up 1980’s nostalgia. I love the additional characters he has included here.
👋 See you next Sunday
If you’ve forgotten who I am, here’s a little bit about me. As always, my calendar is open to chat about your next adventure, crazy idea, or if you’re feeling creatively stuck.
Have a great week,
p.s. If you enjoyed this letter, would you please let me know by tapping on the heart below?