Who’s Going to Bet on You?

One year ago I put something out into the world. Something I'm still surprised I thought was a good idea. Based on the timestamp, I was probably on my third espresso of the day and was at a peak level of delusional self-confidence.

(Some say it's a negative attribute, I'd argue it's a necessary evil for the path I chose)

When I try new things in public, they fall into one of three categories:

1. Why the hell are you doing this?

2. Why the hell are you doing this? That's awesome!

3. Why the hell are you doing this? I would never do that, but I can't look away.

This falls into bucket 3... what did I do? I asked random people for money.

I was reading Million Dollar Weekend by Noah Kagan. There was a section about getting comfortable asking people for money. Heck, if I wanted to start a business, I was going to need to get comfortable asking for money and getting rejected hundreds of times before I got one yes.

I wanted to take some action on this. So I whipped out my phone and drafted this message:

I fired it off to 12 people within my close network.

Of the 12 people I texted, 10 immediately sent me money. One friend even sent me $100!

I was fired up. This was when things started to get fun. Being in the state of delusional self-confidence I was in, I decided to put this on Twitter (never calling it X). I wasn't expecting it to get as much attention as it did, but 18 more people decided it was a good idea to send me money. This list now ranges from founders, CTOs, and family members to a previous yoga instructor.

I had 30 people who were invested in me. Not an idea. Not a trend. Me. It may have seemed like a trivial sum of money to send to someone, but it meant a lot. I didn't want to let these people down.

I decided to take things one step further. I asked everyone for their emails so I could send them updates on how my business was going. At that time, I was starting a preventative health company with my good friend Stedman. Despite deciding to shut down that company. I still kept investors up to date.

Nobody asked me to do this, nor is it required—most people sent me the cost of one overpriced latte (before the tip) and could have forgotten about it. Yet sending out these updates has been one of the best decisions I've made.

This is a way to keep myself accountable. It forces me to stay focused and true to my word. The best part? Just like real investors, these people are now in my corner. They want to see me win. When I launched the preventative health company, many of them wanted to be my first customers. When I felt lost and directionless, they listened, offered guidance, and acted as a sounding board. When I left Dexcom and needed to find contract work, they offered to share my information with their personal networks to help keep me afloat financially.

As I've met people over the past year who have gone out of their way to help me, I ask to put them on my email list of people who have invested in me. This list has grown to almost 40 people.

Every month, these investors receive updates on:

• Wins, Losses, and Asks

• My personal finances and runway

• The successes, failures, and learnings of each business I start and operate

I got this idea from Tyler Denk, the founder of beehiiv—someone who I look up to for how to build brand and trust while building a multi-million dollar business. Because of those email updates, he was able to raise his Series A in 6 days.

Like I said—you don't need to do this. But I'm positive that this is a long game I'm playing, and by laying down these bricks of accountability, I am building a fortress of trust and commitment. Soon enough, I won't just have people in my corner; I'll have them in the arena fighting to help me. This will be my unfair advantage.

Despite it being early, I think this is one of the best things you can do as an entrepreneur:

1. Get comfortable asking people for money.

2. Relentlessly update people who invest in you on your progress and problems.

3. Vocalize asks to people who have a vested interest in your success and more likely to help.

This can be your unfair advantage. You'll have a whole team in your corner, and you'll find yourself moving faster than ever.

Now go find your investors. Everyone’s got some 🙌🏻

You’re Awesome,

Jared

Gentlemen’s Agreement 🤝🏻

I need a favor from you. Every week I spend several hours crafting this email to give you entirely for free. Banger, after banger. Except it’s not actually free.

I love doing this, but I also love seeing this grow (You might say I’m flawed. But you’re not my therapist). To keep this free it would mean the world to me, and my ego, if you shared this with just 1 person who you think would also like this.

They can subscribe using this link here 🙌🏻

I Dig So You Don’t Have To

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