Behind the Scenes at Craft + Commerce 2026: What Changed Since My First Conference

Behind the Scenes at Craft + Commerce

I stepped out onto my balcony overlooking Boise’s state capitol to take a deep inhale, exhale. It was something between “holy sh*t I can’t believe I get to do this stuff,” and “I need to breathe before I meet one more new person.”

I’d just hung out with James Clear (who was delightful, by the way). Walked into a room full of 50+ entrepreneurs I admire, but didn’t all know. Did a photoshoot for Kit. Got chosen by my mastermind tablemates to share my best recent strategy in a room full of my business idols.

And it was only the day before Craft + Commerce actually started.

How Different This Year Felt From My First Time

In 2019, I went to Craft + Commerce alone.

I didn’t know anyone and definitely nobody knew me. I remember finding out about the private mastermind they held, the one I didn’t get invited to, and thinking, “I’m really bummed I didn’t get invited, but one day I’m going to.” No one told me about any happy hours. I definitely didn’t get to go to the speaker dinner. My online business life couldn’t have looked any more different.

I’d sort of ignored the whole networking thing considering I was coming off of brain surgery and taking care of my newly terminally diagnosed dad, Norm. I went on to have my first 7 figure year that year.

A lot has changed since 2019. My business kept growing. My parents both died. I started a podcast. I came out with my first book. And then last year, I spoke at Craft + Commerce. Honestly, between that and my book, everything changed.

Walking into Craft + Commerce in 2026 couldn’t have been any different than 2019. Now, managing my energy has more to do with overwhelm from talking to so many people, and losing my voice from all that talking, instead of the overwhelm of walking into a room full of strangers.

This year was the first time I had to manage my energy much differently. I ducked back to my room, and onto that beautiful balcony, to take a beat before someone asked me another question. I skipped some of the genuinely valuable sessions to grab coffee one on one with a friend instead. I had dinner one night with my team and my friends, Chelsea and Chenell, instead of attending yet another big function.

How “Sammy on the Street” Was Born

Giving myself a moment to breathe gave me the spaciousness to come up with a fun idea on the fly. I told my podcast producer, Michelle, “Why don’t I try to grab creators I love off the street for quick interviews? Then I can include them in my Craft + Commerce recap episode.”

I sent Michelle to the sessions I wanted notes on, and I stood outside the venue to conduct what we started calling my “Sammy on the Street” interviews. You can hear them all in this week’s Craft + Commerce recap episode.

If you want to hear everything I learned, my biggest takeaways, and what I’m doing (and not doing anymore) after talking to some of the biggest names in the industry, you can listen to this week’s episode of my podcast, On Your Terms®, where I share a full behind the scenes recap of Craft + Commerce.

A Day by Day Look at Craft + Commerce 2026

Day 0: I drove two hours from eastern Long Island to JFK, flew to Boise, checked into my hotel, and went to dinner with Liz Wilcox, Pat Flynn, Matt Gartland, Steve Kamb, Shawn Blanc, Barrett Brooks, Jay Papasan, and friends.

Day 1: Mastermind and Photoshoot. The day before the conference started, I got to attend Kit’s private mastermind with a handful of creators and James Clear. So much of what I shared in this recap episode came from what I took away from his talk. Kit’s marketing team also asked me to take part in a photoshoot with a few other amazing creators, which was such an honor.

Day 2: Conference Day, Happy Hour and Speaker Dinner. Thursday was a full day of talks and workshops. I felt so much less pressure this year to attend everything. I spent more time having one on one conversations with people I know or wanted to get to know better, rather than trying to do it all. In between sessions, I grabbed people I admire off the street and asked them what they’d learned so far, why they keep coming back each year, and what’s going on in their business. Afterward, I headed to my friends Shawn Blanc and Barrett Brooks’ happy hour and then to Kit’s speaker dinner.

Day 3: Conference Day, Happy Hour, Podcast and Closing Party. The last full day was packed. I watched the talks on the main stage, which always leaves me inspired and itching to run back to my laptop to implement everything I just learned. After the conference, I went to my friend Jay Papasan and Chenell Basilio’s happy hour, recorded a podcast episode with Beth Nydick, Tarzan Kay, and Courtney Spritzer, then headed to Kit’s closing party to dance the night away. I brought Lindsey and Michelle from my team with me to Boise, and it was so much fun introducing them to the people I love in this business. It was also the first time I could send them to a workshop so I could go do something else I needed to do. It was like having three of me there.

Days 4 to 5: Aspen Buddies, Rest and Travel Home. After so many days of outward energy, I was ready to come down a bit. I like staying in Boise one extra day now, and it turns out most conference goers do too, to catch up with people I didn’t get to see during all the craziness. I spent Saturday with a bunch of my mastermind friends eating, shopping, seeing a movie, and getting dinner. It was the perfect wind down, especially since I’d lost my voice by that point. On Sunday, I went to one of my favorite Boise coffee spots, Form + Function, jotted down notes for my recap episode so I wouldn’t forget anything, and ran into a few friends who hadn’t left yet either. Then it was time to head to the airport, fly back to New York City, and drive two hours home to Long Island.

Listen to the Full Recap

Want the full story, including my “Sammy on the Street” interviews and my biggest takeaways from this year’s conference? Listen to this week’s episode of On Your Terms® for the complete behind the scenes recap of Craft + Commerce.

Links You’ll Love

Listen to my interview with DEATS with Deanna: Can You Actually Say That Online? FTC Rules Every Dietitian Should Know with Sam Vander Wielen → Listen on Apple, Spotify, Website ← link those to the episodes.

I chatted with Holly Haynes about how I’ve pulled back a bit on social media and doubled down on email marketing in our interview on her Crush The Rush podcast→ Listen on Apple, Spotify, YouTube​