Let's Go Tour 2026: Only The Beginning...

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The GTM bets that shouldn't have worked, and did

One grew revenue 50x after half his team quit over the strategy. One brought in 50K signups in a single day with no paid budget. One generated 100M+ views from a stunt that took 50 hours to conceive. One asked every prospect to demo the product themselves instead of demoing it for them.

None of them followed the safe playbook. They treated GTM like an experiment, moved before they had proof, and made bets most founders would never get approved.

HubSpot for Startups documented all 6 stories in the free Bold Bets Playbook. The risks they took, why it was risky, and what it returned.

Read the free Bold Bets Playbook

Let’s Go! So hyped you are here! I am pumping out 30 push ups & yelling “let’s go” as you read this newsletter!

Round 3: We're Running Again, May 28th. Run starts At 7:15 am sharp.

We pull up at 7:00 am at Prince Coffee on Killingsworth Street in Portland, Oregon. Come for the miles, stay for the coffee and the conversation.

Let's Go Tour 2026… Round 1 and Round 2 have been incredible. Prince Coffee is elite, got some miles in, the homies pulled up, and we discussed this article by Patrick O'Shaughnessy, Growth Without Goals. Check it out.

This is simple. I want to create opportunities and experiences for people to connect. An excuse — in the best way — for us to come together. Started with combining things I love: my friends, running, and coffee. Round 1 was for the grand (soft) opening of Prince, and Round 2 took full advantage of this sunny Portland morning! See you this Thursday!

Sharing What's In My Head.

Pete Carroll on Personal Philosophy… Write everything about who you are and who you want to become. Develop a personal philosophy you can stand on when things get tough. It's all a process of self-discovery, which is one of the most empowering things you can do. Truly understand yourself, then be you relentlessly.

This hit home because of what my friend Thomas told me about medical school. When applying, you had to write a Personal Statement, getting crystal clear on why you want to be a doctor and what it means for you. We pivoted to discussing that same exercise for dating and relationships. So I started writing it out. Sent him draft #1 already… (Lock in my guy! haha)

Write, rewrite, repeat. Writing is a forcing function for clarity.

Commitments over goals… I shared this framework with my women's basketball athletes heading home for the summer. Instead of vague goals like "be in shape" or "have fun" — focus on commitments.

• 2-2-2 for 20. Seven weeks at home. Twenty minutes of basketball, conditioning, and lifting. Simple.

• Basketball on court work. Fitness Monday/Wednesday. Lift Tuesday/Thursday.

• Can you go 12/14 in each activity?

• 36/42 on showing up for yourself? Instead of wanting to be the most prepared, you track one thing: did I do what I said I was going to do.

Podcasts I’ve Loved Recently.

1. David Senra & Dana White : the mindset of building the UFC from nothing. The part that stuck with me most was this Bruce Lee quote:

2. Zach Pogrob & The Running Effect Podcast.

   • Produce stuff violently! Keep creating value and putting it out into the world. Podcasts, writing, videos, twitter, art, etc.

   • DEDICATE YOUR LIFE TO EXTREME VOLUME.

   • “Running 10 miles a day solves everything”. There is no way your life won’t change if you wake up before sunrise and run a challenging distance every single day. Discover your uncomfortable threshold.

That's all for this week. Happy Memorial Day Weekend! Hope you're out there sending it on something you love with the people you love most.

Keep stacking those daily deposits and making every day the best day of the year, until tomorrow…

Ferate