Bootstrapped founders have 3 problems

I don’t usually email on Saturdays but I was too excited not to share this with you…

I just had amazing conversations with readers doing $0, $10k, up to $100k per month with their businesses.

Here’s what I learned that will make you a better bootstrapper.

First, some context…

A few weeks ago, we hosted a live session with Sam Parr (founder of The Hustle and Hampton) to talk all things bootstrapping.

I emailed 300 attendees asking if any of them were B2B SaaS or Services founders who’d be willing to jam with me on how I could help them.

Over 50 people responded and I ended up having week-long conversations with a bunch of them.

There were VERY common themes across what people were stuck on.

Are you feeling any of these?

1. Unscalable wins: You’re afraid you haven’t built a true system for customer acquisition… wins feel one-off and you can’t scale what you can’t control

I can promise you that in B2B, there is only ONE KPI that matters if you’re below $50k/month:

Meetings booked. 

People (incorrectly) think you need to be some type of smooth-talking magician to close sales.

That bar is not that high - as long as you have a pleasant attitude and a remotely good product/service, you will close 20%+ of your sales meetings.

This means you are only 5 meetings away from your next customer.

So how do you get 5 meetings every week? 

You become religious about outreach. 

To get to $50k/month at GrowthAssistant, Adriane and I obsessed over a system of templates, warm intros, and follow-up tracking.

It worked. 5-10% of the people we messaged got on the phone with us. 

For every 50-100 messages we were nabbing another customer. 

2. Marketing analysis paralysis: You don’t know which channel to begin with (what if you spend time/money on the wrong choice?)

You have a few primary choices for customer acquisition:

1. Paid ads

2. Content / personal brand

3. Email/DM

There is no ‘set rule’ for what works. ANYTHING, executed well, can scale.

But if you’re bootstrapping right now, here’s how I’d think about it:

Ad prices (CPMs) will only continue to go up as we get closer to election day.

And you probably don’t have an infinite budget for ads.

How about content?

Well, content / personal branding are amazing ways to nurture existing leads…

…But it’s very hard to grow a company and audience from scratch at the same time.

Plus, LinkedIn / X aren’t making it any easier - it’s tougher than ever to link out to your website without the algorithms killing your content’s reach. 

This is why I am a HUGE fan of email + LinkedIn DM outreach. 

Do you have a keyboard, fingers, and some time?

Great! You can hit $50k MRR or more with just this channel.

3. You’re afraid to sell: You don’t know what to say to get people on the phone with you and live sales calls feel awkward

You need to understand how to treat your calls less like a pitch and more like a conversation.

Do you ever notice how weird it is that we change our tone so much in email vs. text?

So many people I know who are concise, amazing givers of advice become robotic “formal” versions of themselves in email.

That’s exactly what happens to you in your first sales calls.

Squashing your inner robot requires understanding + practicing setting the call’s tone, doing discovery, and only pitching when you’ve understood your prospect’s problem. 

Understanding exactly how to solve these issues for readers is the backbone of the B2B Blueprint we’re launching in a few weeks.

If you’re feeling any of the things above, you’re going to love it:

1. I’ll give you everything you need to do outreach - the tech stack, frameworks, and opening lines/scripts - things working right now.

2. I’ll show you exactly how I break down my sales calls and teach my process to the CEOs of my companies. 

3. You’ll get recordings of our actual sales calls - completely unedited. Ones I took. Ones our team took - and not just the wins, you’ll see us mess up, too.

Tap here if you want a heads-up when it’s ready.