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Bootstrapped Giants

This 1 tweet keeps bringing me customers

Published 24 days ago • 6 min read

In 2020, I left San Francisco and moved back to my hometown of St. Louis.

My friends felt like I moved to the middle of nowhere and suggested I get on social media to stay in touch. My first reaction was “YUCK.”

But then a friend said, “Jesse, you have a gift for storytelling and explaining things that will really help a lot of people. Imagine if you could inspire and help tons of entrepreneurs, especially around bootstrapping.”

That resonated and I had the time, so I said: WHY NOT?

My friend Henry Schuck bootstrapped ZoomInfo into a multi-billion dollar business. This week he changed the game by launching an AI that will become your sales team's best assistant: ZoomInfo Copilot.

ZoomInfo Copilot:

• Creates a list of likely buyers
• Researches each buyer's company & decision maker
• Knows the right next steps for closing sales
• Even writes customized messages that are actually good

If your business is selling anything, read about ZoomInfo Copilot, here.

So in April of 2021, I started Tweeting. I fell in love with the process of teaching the response I got from readers like you.

The next month, I tweeted about a business I launched and headed to dinner with my wife.

Later, when I looked at my phone, I saw that I got 10,000 new followers and the business got 400 new leads.

This is that post:

My partner & CEO, Adriane Schwager, said,

"What the hell did you do, Jesse? How am I going to call all these people back?"

The funniest part (and if you follow me on Twitter/X you know this): I recycled that same tweet 20 times! And I got over 2,000 more leads from it.

On the back of that strategy, I scaled my business to $13 million in annual revenue within 3 years.

Now Adriane tweets too. Her following is 13% as big as mine, but she has some bangers, which drive significant revenue for the business.

When I tell people that I want all my companies’ CEOs on social, they think I’m wasting their time with vanity projects. Now that you see the results we’ve gotten, it makes sense, doesn’t it?

And the quality of clients we get is remarkable. At my other company, Aux Insights, half our private equity clients came from social.

Social is also a recruiting tool, a platform for landing meetings, a virtual lounge to get to know future working partners, and a way to find “your people.”

But Jesse, I’m busy running a company, how do I master social too?

I got you.

Start with a single platform. Twitter/X and LinkedIn are the easiest because they’re text-first platforms, but pick anyone that you can create on consistently.

Get your profile page looking right. It’s the first (and often the only) thing people will see about you.

So make sure it clearly says what you do, why people should follow you, and where they can read more about you.

A good profile photo helps. If you don’t have photos you love, use an AI service, like Headshotpro.

Here’s mine:

Start by commenting on popular creators’ posts. It’ll get your profile attention, build your writing practice, and train you to look carefully at what’s working for other creators. I still comment on others’ work to learn.

You’re reading these words right now because I used this formula to get you here.

Not every topic needs this approach. If you’re just posting a question on Twitter, come out and ask. You don’t need a formula. But when you really want to drive results this is the approach to take.

Let’s break it down.

Hook

This is what stops someone who’s scrolling through social media and hooks them into what you have to say.

The best hooks:
1) pique curiosity and
2) promise a clear benefit.

Look at the hook from the post at the top of this newsletter:

100 days ago, I co-founded a business. Totally bootstrapped.
Today, it’s doing $50K in MRR growing 50% per month.
Here’s the story…

Notice all the curiosity gaps it creates?

  • How did Jesse do this in 100 days?
  • What’s he doing to get $50k per month?
  • How is it continuing to grow?
  • What is this company? He didn’t even say its name.

But it’s also offering benefits:

  • It promises a story. Stories are fun.
  • It’s going to reveal how to build a business in 100 days.

Give

Once you hook them in you need to give them value, or they’ll resent you for manipulating them.

Look at Adriane’s post above, about Peter Thiel being the “greatest recruiter of all time” and having questions that help him find 10/10 people.

If she only revealed Thiel’s questions it would have technically qualified as delivering on her hook’s promise.

But readers would have felt cheated. There’s not much value in it. So she added value by explaining why each question mattered to him.

1/ Tell me something which is true that almost nobody agrees with you on?
Litmus test of independent thinking + logic.
The combination can be deadly.
2/ How successful are you going to be?
Helps him understand the person's ambition, vision, and motivation.
As well as the detail and carefulness of their plan.
3/ Do they have Zen-like opposites?
When somebody embodies rare opposites, it shows absolute open-mindedness and quality of thinking.
He prizes this among new hires.

Drive

Here’s where most people miss out. They do the hard work of getting an audience to pay attention. They deliver value. And then they leave their readers to move on to the next piece of content.

You need to drive them to a destination. Have a call to action.

I come from the ad business where the goal of each creative is clear: page views, clicks, subscriptions, purchases, etc.

On social media, people post with no purpose.

When I started being intentional about social media, I ended with a CTA of following me for more. Might sound cringy but if you don’t ask, you don’t get.

Today I value my relationship with email subscribers more, so I follow my most popular posts with a link to this newsletter’s subscription page. Almost everyone reading this came from that form.

Stories

Your best content will come from your experience. It’s how people get to know you well enough to transition from browsers to customers. But it can be hard to start out by putting your story out there.

And even experienced writers struggle to come up with enough personal stories to fill a timeline.

One approach I take is to reach outside my personal experience for stories that highlight my approach to business. These stories can come from articles, books, etc.

Frameworks

My mind operates in terms of frameworks. I naturally break down how things work into steps. So this type of content comes naturally to me.

But you probably use frameworks more often than you realize:

  • When you do something consistently, you go through a set of steps.
  • When you teach a team member, you give them a process.
  • When you tell a client how to work with your company, you give them some guidance.

Those are all publishable frameworks.

Building in Public

In last week’s newsletter I told you about a setback in one of my businesses. Talking about challenges can be hard because it reveals vulnerability. Surprisingly, talking about accomplishments can be tough too because it feels too braggy.

So why do it?

As Nathan Barry, founder of ConvertKit, says, “The best way to be interesting on the internet is to be going on a quest.”

When you do it, people will follow your progress and help you reach your quest. Nathan bootstrapped to over $40 million in ARR by liveblogging every step he took to build his email marketing company.

Many readers have been following his progress for over a decade.

Personal

This topic isn’t for everybody. I understand that some people don’t want to post anything about their families or private lives online.

Hell, even Gary Vaynerchuk, the biggest evangelist for getting businesses to be active on social media doesn’t post his family photos.

But family is a major part of my life. I can’t tell you who I am without also telling you about my family. So I share our memorable moments.

Questions

The other day, one of our sponsors was in our Slack, asking Nak, our COO, how he could track the traffic he’s getting from this newsletter and other sources. I watched the frustration they had with analytics tools and wondered what we could get to solve it.

So I went on Twitter and asked. I got dozens of helpful responses.

Finally, don’t take it too seriously You’ll never believe what my top post is.

When I asked a GrowthAssistant to put together a spreadsheet with stats on the performance of all my posts, the biggest post was a reshare of a collection of Mark Zuckerberg memes.

Meanwhile, one of my CEOs spends hours writing a post and overthinks every word. Relax. It’s just social.

The best part of algorithms’ control of organic social is: If your post sucks, NO ONE will see it.

-jesse

Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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