We live in a world where “connecting” means staring into a 2-inch Zoom box while pretending you don’t look at yourself the whole time.

Like many of you reading this silly little newsletter, I have a new business idea every week.​ And when I say “new business idea,” I mean mostly bad ideas. Think “Uber for parrots” bad.

After selling WeHero and The Impact Job, I did the logical next thing: I jumped to the other side of the table. The buyer’s table.

At Pono, one of our core values is Operational Excellence, which sounds like something you’d find on a corporate mug, but I swear it actually means something around here.

Yup. Real ink. Real paper. Real people holding it in their hands.

There’s a lot that goes into building a business. Ideas, product-market fit, funding, growth… yada yada yada. But my favorite part?

Sometimes I think about how the founding of America was basically a startup.

I always forget how brutal the last 5% of a project is. ​It’s like the boss level you didn’t train for.

I think it’s so easy to let AI take over… well, everything. It’s kind of like the first time I discovered Bitchin’ Sauce.

I respect the endurance.​ Recently I’ve talked to a few founders who spent years in the startup desert. ​No product-market fit, no salary, no exit in sight. Just vibes and ramen.

What if we did it differently? That’s the question that keeps popping up in my head lately. Not “how do we scale faster?" Not “how do we raise a round?”

My wife works for Workday. ​If you don’t know Workday, it’s a giant publicly traded company that does HR, payroll, and finance software for companies that actually read their employee handbooks.

Alright everyone. This one’s a little different than my usual Friday email. I want your feedback on a new project I’ve been diving deep into called Luna.

Every now and then, life hands you a “boss level” challenge. Big workload. Big problems. Big dreams. Big uh-oh. When that happens, I try to go full beast mode.

“When do you throw in the towel?” Honestly… this is the question that haunts every founder more than their bank balance.

I don’t paint. I don’t write poetry. I believe that my form of art is really building businesses. ​Most of the businesses (especially the brands) are really just an extension of myself.

With the barriers to entry basically crumbling in most industries (like, your cousin Todd with a WiFi signal can prompt build a website and suddenly become a "tech bro”) you need to invest in moats.

Let me tell you what I hate. I hate pulling trains uphill. If you’ve ever tried to build a business in a shrinking market, you know what I mean.​

Marketing and sales are damn near everything. Over the last 12 months, I feel like I’ve been back in school except this time, it’s not some fancy college program.

I’d trade all of that in a heartbeat to build cool stuff with cool people I love spending time with.

I share this all to say: if marketing feels like you’re just setting cash on fire while whispering “please work” into the void, congrats, you’re normal. ​

This dude, Mufasa, is not just fired up for Friday.​ He’s got the greatest hype man of all time backing him up. And that got me thinking… Everyone needs a hype man.

We’re talking thousands of years old. Like... companies that were around before your ancestors figured out how to boil water.

There are a lot of great traits to look for in the people you surround yourself with. Integrity? Sure. Intelligence? Cool. But the stand out for me recently is a high bias for action.

If this is your first email, don’t worry, you’re only 99 behind. I thought a lot about what to write today.

Here's a weird phenomenon: when I'm running my own business, every decision feels like diffusing a bomb blindfolded.

AI is moving so fast it feels like I’m watching an avalanche, and my brain won’t stop spinning.

We went to visit Bob's Red Mill! Yup - the oatmeal and flour company.

Stair stepper businesses. Just like all of us unique flowers, businesses grow in lots of different patterns.

The Tipping Point Myth: It’s Not One Big Thing, It’s a Thousand Tiny Things

Alright, I’m kicking humility to the curb today. My wife and I crushed our 2024 goals!

I meet a lot of business owners. This month for example, I'll connect with over 30 founders and owners.And every now and again, I connect with someone that shakes my frame. Makes me rethink everything I'm working on.

I had 8 sales meetings this week. 50% were belly to belly which I love. But I don't think of them as sales meetings.

This little side project is actually a decent business with a huge following raking in 700,000 visitors a day to the site with an audience of over 1 million people.

I LOVE building teams. It's one of the big reasons I love starting companies.

I’m in Bentonville this week meeting with clients, spending time in person with the Pono Ventures team, and riding bikes. Since we’re in the land of Walmart’s HQ, I did a little dive on the Waltons.

Purple cows are one of the greatest business/marketing strategies ever. So today I thought I would share 9 of my favorite purple cows.

This simple business has been right under my nose for years quietly bringing in $6,160 / day.

So you want to start a job board? Great idea. I’ve built one myself, sold it, and can tell you firsthand—this business works.

Last week, I did something a little different—I went on a solo retreat. Yup, just me, myself, and I.

I'm doing the thing. I'm making wine! And no, this isn’t some new business venture (even though my brain is screaming to turn it into one).

I was thinking recently about the people who’ve had the biggest impact on my life. The ones who shaped where I am today. One of those people is Skip Miller. Skip was an absolute legend in Silicon Valley sales.

Look, I love a good business idea as much as the next guy. It’s like caffeine for my brain — gets me hyped and grinding. But here’s the trap I used to fall into: I’d get so fired up by the idea that I’d lose sight of what...

Learn how to start an event planning business with this comprehensive step-by-step guide. From legal requirements to marketing strategies, we cover everything you need to build a successful event planning company.

I love it when you can find little levers in a business that drive meaningful changes. One of our businesses Pono Ventures has been on a growth tear this year creating good (and some bad) results.

5 Sales Hacks: How to Flip the Script, Listen More, and Close Deals Like a Pro

OMG OMG! Our local ski park Mt. Bachelor just went up for sale. This is super interesting to me. I mean, how cool would it be to own your local ski park with the right investor group/partner?!

Losing mindsets are as toxic as the hot pocket I consumed yesterday. Maybe the olympics are wearing off on me, but I have been obsessed with the idea of winning mindsets recently.

I looked at 38 businesses this week for potential acquisition targets. Many have a business that is dramatically different than the business they set out to start.

I looked at 38 businesses this week for potential acquisition targets. Many have a business that is dramatically different than the business they set out to start.

My business partner and I have a lot of weaknesses. But amidst our graveyard of weaknesses, I think we have a few strengths. One of our greatest strengths - we take a lot of shots on goal.

The fact that my cousin is 29 and has this thriving business is not what was inspirational. The inspiration, was that he is 29 and is already aggressively giving back.

Rejection sucks. Or at least it did for me for a long time.

As entrepreneurs, we all dream of the blue ocean. Not the blue ocean that you can see from your vacation villa in Tahiti (maybe next year Ben). We dream of the blue ocean for business that has few to no competitors.

I've been thinking a lot about legacy businesses recently. Basically the business equivalent of a family heirloom that doesn't gather dust.

Once upon a time, I was terrible at firing. I would drag it out with the hope that the team member would improve, or maybe even quit before it came to a firing decision. This was a massive waste of time and money.

The hardest thing for me to say - No.I'm a yes man. Being a yes man can be beneficial, mainly for opening doors and making new connections. Also makes me happy to make people happy.

Getting your dog groomed isn't the only thing that's expensive these days. Businesses are expensive!

You lose 36% of your investment in GameStop. "Expected." Then, your dog somehow got into the neighbors yard and ate one of their chickens. "WTF?!" Then you get a flat tire on your way to work. "Classic."

Our Super Power - Speed In Testing 🐇 This mindset has probably saved us millions of $ in time and money.

This is what matters when it comes to hiring. There are so many things that make up a good hire. I try to keep my hiring methodology simple.I look for these traits in every candidate:

Shifting my mindset for better performance. Sometimes I feel like a race car driver that's building his car when the race is already 20 laps in. I'm in the wrong mindset in the wrong phase of the race.

I think a lot more about risk than I have in the past. For the bulk of my professional life, I've been "risk-on" (god that was a fun decade) but now I analyze investments, deals, clients, and most importantly, my time, through a n

I think a lot more about risk than I have in the past. For the bulk of my professional life, I've been "risk-on" (god that was a fun decade) but now I analyze investments, deals, clients, and most importantly, my time, through a n

Can I give you a check for $50,000 today? Yes please! Sometimes I get attracted to a B2C business but remind myself that B2B businesses are the best for so many reasons. Here is one from a few years ago:

An investment opportunity came across my desk this week that is much riskier than what I typically consider putting time and money into.

As more and more of our friends have kids, our Saint Patrick's Day celebrations have really changed for the better 🍀.

Finding the one metric that matters. It's easy to get overwhelmed with data. Number of leads, top line revenue, how many beers are left in the office fridge. The list goes on and on.

For those of you that are new here, every week I send what I call a 1x1x1.​ One learning or interesting item from my week. One interesting item/tool of the week. One image from my life. Let's dive in 👇

For those of you that are new here, every week I send what I call a 1x1x1.​ One learning or interesting item from my week. One link to something I found interesting on the internet. One image from my life. Let's dive in 👇