^{Featured Startup!}

Pangea

Last week week I met Matt a prolific traveler (he's been to 118 countries!) and founder of Pangea. 

They're launching a cool new social travel app which keeps track of your friends' travel plans, visualizes where everyone will be in the future on a map, and notifies you when your paths will cross.  

Their beta is free on the AppStore, and he's interested in getting feedback before they launch more widely next month. 

Check it out, send me a friend request, share it with a few friends, and let him know what you think! 

If you’re a startup, and want a (free) feature on this blog. Reply to this email.

^{Cuts x Habits}

Do you want Habits swag?

As many of you know, I’m constantly wearing Cuts Clothing. So much to the point where they proposed to hook our team up with gear for the Morningstar conference next month.

Which got me thinking? Should we raffle some off through a giveaway????

If we were to…I strongly suggest you:
→ Download the app and create a profile
→ Follow Habits on Instagram

^{Main Story:}

Most Conferences Are a Waste of Time

Let me start with this: most events and conferences are a massive waste of time, especially if you're a founder trying to grow your platform or sell your product.

It’s like raising capital. It gives you a temporary shot of adrenaline. A little high. A few people clap. But unless you’ve got a critical role, you’re just burning time and money to be another lanyard in a buffet line.

Want to know how many conferences I’ve actually paid to attend for Habits? Zero. Zilch. Nada. If I’m not speaking, pitching, or getting comped, I’m out. The math just doesn’t math.

Let me tell you about the three events that actually moved the needle for us:

Innovation Showcase – Indianapolis

Back when it was just Veera, Matt, and I. We were trying to figure out if Habits had legs…like real scalable legs.

We entered the pitch competition for a $10K prize. Didn't win it. But we did get a free booth, told our story to a bunch of strangers, and practiced our pitch in the wild. And bear in mind this is all pre-TikTok, pre-following, pre-anything.

It wasn’t glamorous, but it was honest. And that was the win.

If you’re early, forget winning. Just get in the room, tell your story, and sharpen your sword.

1871’s Fintech Showcase – Chicago

This one was huge. I literally moved back to Chicago for it. We were one of 47 companies, and yeah winning helped.

We announced our raise. We launched our mobile app. We spoke on stage.

We didn’t win any cash, but we got crazy visibility. A few LinkedIn posts hit over 200K impressions. One Instagram post crossed 300K views.

That’s what a win looks like. No fluff. Just ROI.

Visibility, momentum, and a spotlight > prize money.

Morningstar Conference – Happening This June

This one’s a no-brainer. Like 1871, it’s our target audience in one room. It’s a platform to speak, a chance to demo new produts, reinforce our value prop, and get our team together.

And it truly is the butterfly effect in action. Here’s what I mean…

• We apply to 1871’s Fintech Innovation Lab

• Habits gets accepted in September

• I move to Chicago for 6 months

• We close our largest VC investor in October

• 1871 sets up a Morningstar tour and we meet their C-suite

• They casually mention a conference. I ask for an intro to the SVP who runs it

• A couple months later, I’m in that SVP’s office

• Habits wins 1871’s People’s Choice Award out of 47 startups

• I send the SVP the win

It’s a lot easier to connect the dots looking back than forward. As always, just keep swimming.

But Why Do I Hate Conferences?

Why would I drop $500–$750 on a ticket, $800 on hotels, another $500 on food and transport (plus burn a few crucial workdays) just to be another dude in a blazer listening to a founder who raised $10M in 2022, probably has minimal capital left and quietly downsizing his whole staff but phrasing it as “we’re going all in on AI!”

All while getting pitched by mouth-breathing sales reps selling me:

• A no code workflow automation that I don’t need

• An AI sales agent I’ll never use

• Fractional CXOs who “10x’d” some SaaS startup in 2021

And I get the irony, I sell too. I pitch Habits every day. But at least I’ve lived this sh*t. There’s a difference between evangelizing and spray-and-praying in the expo hall.

Always Ask: What’s My Angle?

If I do go to a conference, I’m walking in with a plan. A real one.
Not “networking.” Not “good exposure.” A f***ing plan.

I’ll ask myself:

• What’s my wedge?

• Who are the 3–4 people I have to meet?

• How will I stand out?

Sometimes that means creating the event within the event.

I’ve literally considered printing a fake sign, sticking it by the JW Marriott elevator bank saying: “Habits Happy Hour: 4–6pm. No sales pitch. Just drinks.”

Hand out tickets. Rack up a $4K bar tab.
Show up. Make noise. Go home.

Is it scrappy? Yep.
Could it flop? For sure.
But at least it’s got teeth.

Create your own moment if no one’s giving you one.

The Harsh Truth

No one gave a sh*t about me or Habits until we had a following and a few checks cleared. Now? Everyone’s interested. Funny how that works.

Until we’ve got millions in the bank, I’m only showing up when:

• I know the room

• I have a reason to be there

• Or I’m invited and already have an edge

Otherwise? I’m staying home. And that might just be the best ROI of all.

Don’t beg to be in the room. Build so they need you there.

Feedback for Jack

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What’s Coming Next?

I figured next week would be fun to dive into how I cold DM, LinkedIn message, and email various audiences to get Habits off the ground, and keep us running.

But in the meantime, have a wonderful MDW!

Sharing Is Caring

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