Stepping into your most formidable self (Ricky Weekly #29)

This is where I share 3 things every week with my friends and anyone else interested.

Announcement: David and I are building again. For now, we want to help you improve your relationships. If that’s a goal of yours this new year, take our Stronger Relationships 2020 Pledge to make it official. We’ll keep you accountable and share with you something we built that could help when we’re ready.

A picture from my life:

Happy new year 🎉! I celebrated with some friends I haven’t seen in a while. Here’s us doing the Asian squat together.

Thing on my mind:

Two week ago, I went on a train ride with Wefunder to visit entrepreneurs in various cities across America. On the trip, I noticed that there were lots of city-based, themed accelerators, fellowships, competitions and diversity-oriented entrepreneurship programs. This feels like a good development for the world. Just ten years ago when I was in school, the only game in town was Y Combinator.

But coming from Silicon Valley, it’s hard not to see these programs as trying too hard to replicate the magic of Silicon Valley. For entrepreneurs participating in these programs, it’s hard not to notice the gap in quality or see that the good ones are being taken advantage of because the only game in their towns want an arm and a leg in return. It begs the question, “Wouldn’t the best entrepreneurs simply find a way to get to the valley?” or “Why would the best entrepreneurs bucket themselves as only a diversity or a local candidate or participate in any program at all?”

The answer is probably that even if you’re the Lebron James of whatever you’re doing, it takes time to develop the confidence to step fully into yourself.

What do these local accelerators, fellowships, competitions, diversity programs provide?

1) The right kind of community. Even though on the internet you can find almost all the knowledge you need and even people to talk to, a community of peers in the real-world is better. The programs are self-selecting mechanisms to make the same kind of people come together. “Kind” could mean whatever is meaningful to that entrepreneur: shared city, school, ethnic background, socioeconomic class, company stage, industry, etc. Being able to see someone who looks like you or sounds like you or share the same values as you on the same journey builds camaraderie and helps you draw strength from them. When someone who shares your attributes succeeds beyond your wildest dreams, it makes you think you can do it too. This is why it’s easier for Stanford kids like me to think they can be the next Instagram or Snapchat because it seems like they were just getting drunk on campus with Evan Spiegel or Kevin Systrom like, yesterday.

2) Validation. While you need to pass a certain confidence threshold or have a certain disposition to start up, once you’ve started, your confidence continues to swing up and down almost by the hour and that feeling is unbearable. Having seemingly credible people put a stamp on you to tell you they believe in you helps smooth out the ups and downs for a while, and once you buy into the credibility of the group you’re now in, your baseline confidence increases. The bigger the brand, the stronger the effect, but smaller programs looking for founders like you also means you have a higher shot at getting in, and that’s useful because often times the best programs in the Silicon Valley seems too unattainable.

3) Resources. Even though there’s money in Silicon Valley, it feels daunting to go and get it because it’s far and it requires resources and time to break into the network. “Paying a visit” to the valley is not nearly enough because it takes many more visits, and that’s untenable for most. So yes, if you need resources, even if you know what you get from investors locally is a bad deal, you take it and you’d count that as a win.

The most important thing here is probably still confidence because confidence gives people a chance to grow into their most formidable selves, and from there they can figure out the other stuff.

I led an entrepreneurship club when I was a student at Stanford. It was one of the biggest clubs on campus with the most resources so we did a lot of things. Too many things, I thought. But I understood the role every program played. To bring it all together, I used to talk about how our job was to nudge every student along the entrepreneurial journey, regardless of where they are on the journey. We had programs targeting students who have never heard of startups (I was one of them), programs teaching them the ins-and-outs of venture, programs to get students to hack on something over a weekend, programs to give funding to people who need a final nudge to go get it, etc. Virtually any student at Stanford would’ve been able to find a program that spoke to them, and when they participate in it, they’d be nudged forward a bit with a little more inspiration, knowledge, confidence, community, funding, etc. We even visualized it like a progression.

Imagine an arrow pointing down from Inspire —> Create —> Fund.

So to sum it up, “programs” help increase baseline confidence and tamp down the self-doubt that you feel on a daily basis as an entrepreneur. Something like this.

Fortunately for me, I was able to get into two of the “programs” in the world that create the biggest delta in terms of confidence: Stanford and Y Combinator. My confidence level still swings up and down, but my baseline is much higher, and with experience I feel much closer to my most formidable self.

Piece of content I recommend:

Terrace House: Tokyo 2019-2020 on Netflix

I’ve been a fan of the entire Terrace House franchise and have watched every single episode ever. I’ve even been watching the latest episodes from Japan that are not available on Netflix USA yet.

If you haven’t seen it before, the latest season is “Tokyo 2019-2020” and it’s very good, but it’s still going so you’d be left with a cliff hanger. If you want to watch seasons that have ended, I recommend “Opening New Doors” and “Boys and Girls in The City.”

The reason why I love it is because it’s the most wholesome reality show. Imagine a group of people living in a house, but the drama is that the guy who wants to be a chef isn’t working hard enough towards becoming a chef and the housemates stage an intervention. Yeah, I know right. It’s also hilarious because there are commentators who watch it with you and they always say exactly what you’re thinking.

Here’s a trailer I found for Opening New Doors that has English subs

As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My latest essay is called Single-serving friends