Three Ways to Approach Your Startup Like a Pro (Encore)

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Why This Episode Exists + Nerdy Stuff Not In The Pod 💡

I love the series of episodes we’ve done on the things our best founders do that average founders don’t. No exception here, and some good, nerdy, behavioral science at the core of their actions (as usual).

• 🎯 The Specificity Paradox: Behavioral research shows that narrow claims (like "730 to 800 GMAT") are perceived as more credible than broad ones, even when they promise bigger results. This taps into what psychologists call the "precision-credibility effect."

• ❌ There’s fascinating research on "anti-marketing" from behavioral economics - when companies explicitly say who they're NOT for, it triggers what's called "reactance theory," where excluded people often want the product more. The GMAT tutor unknowingly tapped into this by requiring 720+ scores.

• 📈 The Uber driver comedian story is an example of what Andy Grove (who wrote the classic, High Output Management) called "high-leverage activities" - actions where the potential upside vastly outweighs the downtime. Each passenger was both practice audience AND potential industry connection, a 2-for-1 leverage point.

• 🎄Category Velocity: Frank Sinatra's Christmas strategy illustrates "temporal bundling" - when products draft off predictable behavioral patterns. The best founders don't just pick categories, they pick ones with built-in purchase velocity (like holiday music's annual spike).

And that’ll do it 🤓 

Have a great week!

Pod References

• XLR8 Dev

• Tacklebox

• Hey Jealousy

• Put Your Ass Where Your Heart Wants To Be

Timestamps

• 00:30 - Listener Child Therapist Idea Email

• 05:42 - XLR8 Dev

• 06:50 - Live in Reality, and Choose Where You Compete

• 10:45 - Categories

• 12:57 - Anti-Marketing

• 17:11 - Put Your Ass Where Your Heart Is

• 19:45 - Bonus - Value First

• 21:00 - The End

Transcript - Feel Free to Read it Like a Long-form Article:

Today, we’re going to piggyback on the episode from two weeks ago.

That one was called Two Ways to Approach your startup idea like a pro. This week, we’re going to do what 7 minute abs did to 8 minute abs and do you one better. We’ve got three more ways to approach your startup like a pro.

Here’s why.

The episode from two weeks ago did really well. Lots of people reached out, lots more people than normal listened, and lots of emails came in asking follow-up questions. There was a bit of a buzz, or as much of a buzz a niche podcast about starting businesses while you’ve got full-time jobs can have. Maybe like a low hum, like when somethings wrong with your furnace.

Anyway most of these emails asked for a deep dive on systems thinking - specifically, on the processes entrepreneurs should systematize and the tools to do it. I love the idea, but it’ll take some work on my end to flesh it out. And, it’s probably better as a written post anyway, so it can be referenced and have links and all of that. I’ll get it out soon-ish, so if that’s of interest to you and you aren’t already on the newsletter list, head to gettacklebox.com and sign up when you get accosted by the pop up.

A handful of other emails asked for the other things pros do that amateurs don’t. The low hanging fruit - either mentally or tactically. The counterintuitive stuff someone who hadn’t started a business before would miss.

That sounded like a wonderful Sunday to me. Spending 12 hours looking through old notes and founders deep diving on what, exactly, separated the best founders we’ve worked with. I’ve come up for air on the other side with three favorites.

And that’s what we’ll talk through today. Foundational stuff. Mindset stuff. Tactical, mental, and maybe a touch of emotional. There will be a Gin Blossoms song. It’ll make sense later.

The goal is to make the most of this opportunity you’ve got with your idea. The stuff today should help with that.

But first, an email that warmed my heart and will hopefully light a fire under your butt from someone who listened to that episode two weeks ago and put it into action.

Here it is.

“Hey!

Love the podcast (editors note - I could’ve cut that, but you know how much I love flattery).

I’m working on an idea that’s going to help support child therapists. There’s a massive child therapist shortage, which is, obviously, not good. I am not a child therapist myself, but I work in an adjacent space and have seen the problem, and the toll it takes, first hand. I have some ideas on how it might work - I think maybe a marketplace where a therapist with availability in a different school district could take overflow appointments from a therapist that was overbooked or something - but I know I need to speak with way more therapists first.

I’d planned time to write and send cold emails to ask people to chat but after sending 10 and getting no replys, I lost steam. It felt like I was screaming into the void.

Then, I heard the episode and thought I could automate this. So, I hired someone off fiverr to find 1,000 email addresses for child therapists at high schools in the surrounding states and put them into an excel doc. Then, I had a different freelancer off fiverr set up a cold email drip campaign where the therapists each got 2 emails - one asking for a call, the second asking for a call again but with a three question survey attached in case they didn’t have time to speak. I set up a quick landing page describing the problem I was solving, a calendly for people to reach out and schedule time with me through, and three different versions of the first email to test to see what resonated.

The whole thing cost under $200, and I’ve done 10 calls and have 35 more scheduled. I’ve learned more in the past week than in the past 6 months. I have a dashboard where I watch people open emails and fill out surveys and schedule time. Systems are awesome. It feels like I have a team. This is so cool. ”

Woooo boy does it feel good to get that email.

I always think of systems thinking as binary. Most people don’t know it’s an option. Once they do, the light switches on. There’s opportunity for systems everywhere that repetitive tasks or tasks with no potential differentiation or uncomfortable tasks exist.

If I had one piece of advice for someone who wants to be a systems thinker but isn’t yet, it’d be to pick something with zero stakes and build a system for it this week. Use Zapier to create a chore list that sends an email to you and your roommate on Sundays. Create a Zap that sends you an email each morning to remind you to bring an umbrella if there’s over a 10% chance of rain that day. Peruse fiverr and hire someone to scrape the internet for something, or compile something, or send something for you.

Fluency in the tools that build the system is critical. If you’ve never used them there’s no way you’ll be able to see the potential. The barrier for systems thinking is always comfort - you’ve probably never done anything like this before and it’s odd to prioritize time over money. But that’s the game.

Last week was about using systems thinking, and becoming fluent in the tools that’ll facilitate it, so that you can focus on the few things that’ll truly differentiate you.

This week is about those differentiators.

Three ways to lean into them. To get the most out of them. To identify them. And we’ll dig in with a little help from Frank Sinatra, a GMAT course, and a comedian who drives an uber. And we’ll do it… after…. a little smooooth jazz.

Live in Reality and Choose Where you Compete

Do you know what Frank Sinatras most popular and fastest growing song on Spotify is?

Maybe it’s My Way? That’s life?

Nope. It’s Let it Snow. Also in his top 5 songs are jingle bells and have yourself a merry little Christmas.

Are those great songs? Originals? The things we think about when we think Frank Sinatra?

Of course not. They’re all covers.

So why are they his most popular songs?

Because they have jobs. During the holidays, people play Christmas music. Every year, with no exception, the conditions exist for them to choose Christmas music from November through the end of the year. And, while it seems like there are tons of options for holiday music, there actually aren’t. There are fewer than 10k holiday songs listed on Spotify. There are 80 million total songs. They hire Frank Sinatra’s holiday music to do a specific job, and they do it year after year.

Humans tend to create infrastructure and stick to that infrastructure. Most of the time, people do the same thing this week as they did last week. They listen to holiday music each year which means that the Christmas songs Frank Sinatra writes get played over and over and will eventually tower over all the rest of his music in terms of play count.

There are no other hard and fast scenarios where you must play a Frank Sinatra song 15 times in 30 days. So, the Christmas songs will eventually rule the catalog.

So what’s this got to do with our professional founders?

Two things.

First, they understand that they cannot change people. Ever. People will do today what they did yesterday, and no amount of cajoling or marketing or data will change that. In fact, it often hurts it.

If Frank Sinatras grandson came out next year and spent a ton of money to create ad campaigns to get people to play New York, New York during the holidays instead of Let it Snow because it’s objectively a way better song and a better tribute to his late grandfather, it would make absolutely no difference. And, you instinctively know how silly that sounds.

But entrepreneurs do the Frank Sinatra grandson pitch all the time. They say hey - I know you currently use excel to track all your potential hires, but you should really use this dashboard I created. And instead of hiring aggressively only when you need someone, you should hiring passively at all times to fill your funnel. It’s better for you. Trust me. Wanna buy?

Amateurs want their customers to change to fit what’s best for the entrepreneur. They build SaaS businesses because they love getting subscription payments. They build dashboards and platforms because they think that’ll make it easier for them to raise VC funding.

Pro’s know they’ll never change their first customers. They need to find people that already believe what they believe and are already trying to change. I use the analogy with our startups all the time and it can’t be repeated enough - You’ll never get your first customer to leave their house to go buy an iced coffee, but you might be able to get someone who’s already going to get an iced coffee to try yours instead.

Your job, as a pro, is to be a student of your customer’s process. To know exactly what they do, what they want, and how they’re going about it. If they don’t prioritize the problem you’re solving, they aren’t your first customer. If they do, how are they solving it? How can you work within those confines to help them solve it 3-5x better?

They listen to Let it Snow because it’s christmas and let it snow fits in alongside chestnuts and gifts and family. And it’s on the christmas playlist spotify puts out.

What’s that for your customer?

I mentioned that there were two important things that pros did with the existing infrastructure insight.

Here’s the second.

They take advantage of categories. Let it Snow is a holiday song, so it gets played at holidays. And never any other time of year.

These categories exist everywhere, and your customer has them. Your customer will drop you in a category and assign all the characteristics of that category to you if you don’t purposefully choose it.

Here’s an example.

At some point a few years ago, people started making the case that Die Hard was a Christmas movie. I searched on Google Trends and I can tell you exactly when that conversation started in earnest - 2016. Searches in December spiked. And, now, every year, around the holidays, the movies’ popularity explodes, and it’s actually doubled every year since 2016. The rest of the year, and before 2016, interest was low, and flat.

Someone changed the category of the movie Die Hard from an 80s movie that some people liked and watched nostalgically once in a while for unpredictable reasons to a Christmas movie people watch every year for predictable reasons. New category, massive increase in revenue, same product.

If you’re selling to a customer, what category will they naturally put you in? How can you actively choose a different category that’s more helpful for you?

My favorite example is the perfect bars I eat for breakfast. They’re peanut butter and delicious. And they’re refrigerated. They sit next to the yogurt at the grocery store. So, I put them in the category of yogurt. Healthy. Fresh. Perishable.

Except… that when you read the label, they aren’t perishable. They don’t even need to be refrigerated. It’s a brilliant choice by the manufacturer to change the category. Next to a bunch of other protein bars, they wouldn’t stand out. Next to yogurt, with no other bars in sight, they do.

Knowing existing infrastructure and categories lets you choose where you compete. The exact moment. That’s a choice pros make and amateurs leave to chance.

Who Won’t You Help? The Value of Anti-Marketing

Amateurs try to build stuff for everyone. If you listen to this podcast, you know this already and are actively trying to avoid the mistake.

Pro’s have a secret to make sure they avoid it. They use anti-marketing.

When you don’t have much of a brand or any social proof, it’s hard to build trust in the 6 seconds of attention you’ll get from customers in your cold emails or social ads or mailers or whatever.

Often, the fastest way to build fast trust is to describe who you aren’t for and what you don't do, rather than who you're for and what you do.

This is hard, because we’re entrepreneurs - our instincts are always that we can help everyone. Isn’t that the point?

But anti-marketing, calling out exactly who or what you’re against, can usually build a brand faster.

During the early days of Tacklebox our strongest ads, by far, were the ones that said we were anti-vc. This pained me to say, because I knew in the middle and long run I wasn’t going to be completely anti-vc. I think it has it’s place. But, I was great for and aligned with the people who were building businesses and didn’t want VC early on. So, calling them out let them know something serious about me. It’s usually more likely you align strongly on what you’re against vs what you’ve built, during the early days.

If you have something controversial and state it clearly, the people who also believe it will gravitate towards you and you’ll create trust.

It’s the extension to seth godins people like us do things like this. People like us don’t do things like this. And it’s powerful.

A company came through Tacklebox a while back helping people on the GMAT. The guy running it had a system and it worked extraordinarily well. For people scoring a 600 out of 800, he could get you to a 700 out of 800. But where it really shined was for the people that were scoring 730 or 740 and had hit a wall. The ones who needed an 800 to get into harvard or stanford or the best of them all, unc chapel hill.

He realized this during the program and pivoted his messaging from “we’ll help improve your score by 60-150 points, with all sorts of detail on his methods and timelines and cost, to:

“We help people who consistently score 730 - 750 get over the hump and finally get that perfect 800 that’ll get them into Harvard.”

Below it, he said “to work with us, you must show proof that you can score above 720 already.”

Pre-orders exploded. There was no talk of the method - that didn’t matter. The act of choosing who it was for was the most powerful marketing technique. And the hardest. He said he had to drink three beers before he got the courage to hit go on the ads. That’s how you should feel. Maybe the beers are a kombucha or a long run, but this shouldn’t feel comfortable. And pros know that’s the feeling to chase.

Also, he got a ton of emails saying “I can’t score 720 yet, but can I please get into the course?”

And now, it’s time to shoehorn in that Gin Blossoms quote I promised. I’ve been listening to 90s rock radio on spotify and I’ll tell you what, Hey Jealousy still gets the blood flowing. What a tune. And there’s a line in it that I thought belonged here:

“If you don’t expect too much from me, you might not be let down.”

Choosing helps you narrow in on the value you need to provide. The GMAT person no longer has customers expecting to go from a 600 to a 710, or 550 to 650. Customers of all types with all different goals and work ethics and base levels of competence. All he has to do is work with the best of the best and get them over the hump. Far fewer expectations.

There’s a great quote by Jerry Seinfeld about this:

• “It’s one thing to create,” he says “it’s another to have to choose. ‘What are we going to do, and what are we not going to do?’ This is a gigantic aspect of [artistic] survival. It’s kind of unseen—what’s picked and what is discarded—but mastering that is how you stay alive.”

So… who won’t you help?

And how will that help you position yourself to the people you will?

—

Put your Ass where your Heart is

There’s a book by Steven Pressfield called Put your Ass where your heart is and I didn’t think it made sense to create a title from scratch when the absolute perfect one already existed.

It’s self-explanatory.

It’s also criminally underused.

A friend of mine lived in Minnesota for years with a roommate who I believe was in pharmaceutical sales. But, he always wanted to be a comedian. There wasn’t much of a standup scene in Minnesota, but apparently he’d grind it out, doing shows when he could, coming up with new material, putting it all online.

Then, one day, for no real reason - or at least no reason that I know - he quit his job and moved to LA. He took a job as an uber driver and focused on comedy shows at night. He’d try to have a show every night of the week. During the day, driving his Uber, he’d give each guests a half-joking option - either listen to my standup and you don’t have to give me a tip, or don’t listen to my standup but you better tip me. He practiced bits all day, focused on the rear view mirror, seeing what landed. He’d take that feedback to his shows at night.

One day, the person he was driving had a friend who ran one of the bigger comedy clubs in the city. He introduced them. Now, the comedian is a regular at that club. Apparently, he’s filming a pilot for a show as well.

I’m not saying you should move to LA or NYC or SF. I am saying that the way most people are successful is through serendipity. Through increasing the number of potential interactions with people that could potentially help them.

If you’re building software for nurses, you damn well better be in a hospital.

Wherever your people congregate - whether in-person or virtual - be there. All the time.

In hindsight pro’s always talk about luck. I was lucky to meet this person or to be in this room or be introduced here or there. A huge portion of that luck is having their ass where their heart is.

Amateurs try to average their way to success. Sure, the comedy clubs are in LA. But I’m in Minnesota. Maybe I’ll go out there every month or two. They get 85% of the way there… they create great content, they put up great videos, but… they don’t take the real step to give it all a chance. Being surrounded by the people that can help you make the leap is a cheat code. If luck plays such a big factor… optimize for it. Increase your chances.

Pro’s take that seriously.

And, one 30 second bonus, because it’s top of mind.

I get about 30-50 emails a day from PR agents looking to get their client featured on Idea to Startup as a guest. It’s infuriating. We almost never have guests - though we’ll likely have one next week. And the guests I pick are so purposeful, and the guests these PR folks suggest are so random.

Everyone from Paris Hilton, actually, to random mid-level employees at banks to people with new music coming out.

Sifting through these each day - because I’m worried if I batch filter or delete I’ll miss Jeff Bezos or something - is the bane of my existence.

Until yesterday. I got an email with the subject line “just gave idea to startup 5 stars and a review on itunes.”

And on the inside was a screenshot of the 5 star review. Then, the PR person went on to pitch their client like everyone else, but I paid way more attention. I might actually have her on - she was interesting.

Pro’s recognize that they need to create value in the first interaction with anyone that they want to become a client or talk on the phone or get anything useful from. You can’t just take. You have to give. And pro’s figure out how to create that value.

49 emails from lazy PR people yesterday.

1 email from a pro.

The End

This stuff is all hard. It’s uncomfortable to choose where you’ll compete or choose a category or try to create value within someone else’s system rather in one you own.

It’s hard to move to LA and it’s hard to think about how you can create value to a complete stranger in an email.

But that’s the good news. It means most people won’t do it. But you will, because you’re a pro.

And then you’ll figure out how to automate it and systematize it and then you’ll scale those systems and you’ll have a business.

And when that business grows and grows you’ll reach back out and we’ll go have three beers to celebrate. And we’ll listen to the gin blossoms. And all will be right in the world.

—

This was the idea to startup podcast brought to you by Tacklebox. If you’ve got a startup idea and a full time job, head to gettacklebox.com and join the membership. We’ll help you start your business right.

And if you made it this far, a 5 star rating and review on itunes or spotify or whatever is a huge help.

And… have a great week.