Deeper Business

Build your business - and your business-building intuition with foundational frameworks and practical application.

May 17 • 5 min read

The canine-inspired strategy I used to meet new people


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When I leapt out into business full-time in 2021, you’d think I’d have a ready-made network of clients.

I worked at McKinsey and Nike! I went to Harvard Business School!

That “strong network” was absolutely perfect for being a high-powered fractional marketer or brand strategist for venture-funded organizations...

...and terrible for Fractional Operations consulting for the smaller, expert-led organizations I actually wanted to work with.

I knew no one in the space.

My local networks? They were filled with other beginning soloists or businesses not in a position to hire someone like me. And the larger organizations I found through entrepreneurial funding worlds and pitch groups actually laughed at me because I hadn’t previously scaled or sold a funded business.

(I remember that super awkward networking attempt very clearly.)

Let’s recap: I had no ready-made network, even with spotless credentials. I didn't have great access to the people I need.

Most of us respond to this by trying to "network harder".

More events. More coffee chats. More cold outreach. More LinkedIn scrolling.

But the problem often isn’t effort. It’s trying to build a network from scratch.

That’s when I enacted my very favorite network expansion strategy: the puppy dog strategy.

Through my ex-McKinsey connections, I was introduced to Paul Millerd, author of the Pathless Path (at the time, it was still Boundless).

Paul was the exact kind of person I was: highly credentialed, highly uninterested in spending the rest of his life inside corporate structures.

So, like a puppy dog with an older dog sibling, I followed Paul figuratively (not literally) around the internet.

Who he followed on Twitter? Interesting.

Which guests he had on his podcast? Entirely new worlds.

The communities he talked about? Music to my ears.

And then I repeated the process with the people he introduced me to.

I “met” Khe Hy of Rad Reads, Tom Critchlow, and Tiago Forte of Building a Second Brain. Through those worlds I discovered people like Anne-Laure Le Cunff of Ness Labs and Corey Wilks — who I’m actually meeting in Minneapolis next week for a mastermind event.

Paul had already done some of the work for me.

He had already curated people he respected, communities he valued, and ideas he cared about.

Instead of trying to randomly find “my people,” I borrowed his map.

Paul wasn’t the only person I followed around the internet.

Through more wandering, I found a Fractional CFO/Ops person who seemed to be doing the kind of work I wanted to do — someone a few years ahead of me.

So what did I do?

I joined the same communities she joined.

That’s how I found places like The Upside, Jay Clouse’s The Lab, and Jay Acunzo’s Creator Kitchen — communities that shaped my client roster, reputation, and skillset.

I’d literally see her face on a sales page or LinkedIn post and think:

“Well… if she’s there, I probably belong there too.”

This isn’t just a strategy for creators or online business owners.

Want to get on the speaking circuit? The easiest path is often through someone already speaking who can make introductions for you and pull you along where they go. It’s a little like opening for a main-stage act and joining the tour.

Want to find local networks? Find someone a few steps ahead of you and look at where they spend time.

Someone else has often already spent years figuring out which rooms are valuable, which communities are generous, and which spaces actually fit.

Why start from zero if you don’t have to?

And AI is surprisingly useful for this. Find a peer, a “competitor” or someone a few years ahead of you and ask AI to pull together:

  • podcasts they’ve guested on
  • communities they belong to
  • conferences they speak at
  • collaborators they appear with

You’re essentially reverse-engineering the network map.

This approach is just one “Expand” approach in the Relationship Rhythms program.

Because relationship building shouldn’t feel random.

Over 9 weeks, you’ll work through challenges designed to help you intentionally build the relationships that build your pipeline.

In the first three weeks, you’ll map your network, understand how strangers become clients and champions, and build a simple system for staying on top of it all.

For the final six weeks, you’ll receive prompts and outreach ideas so you know exactly who to reach out to and what to say.

Plus: over 50 email templates and all the supporting resources you’ll need.

Join before June 1 and you’ll also receive live bonuses: monthly Q&A sessions during the summer and CRM office hours to help you build the Relationship Rhythms approach into your own system — or use the one I provide. (Members, check the Circle community for your 10% discount).

NEW EPISODES

Build it or buy it? Vibecoding with Joe Casabona

In this episode, we’re joined by Joe Casabona. He’s been deep in the vibe coding world—building iOS apps, beta reader tools, and more—and has strong opinions about what’s worth your time and what isn’t.

We get into what vibe coding actually is, which tools people are using, and how code goes from running in a sandbox to something real people can access. This isn’t a “vibe coding is the future” episode. It’s an honest look at the tradeoffs—security, cost, opportunity cost, and the sneaky way tinkering can start to parade as productivity.

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Loved talking with Anna from Strange Birds about Leaving the Casino!

We get into:

  • Why and how the casino targets the most vulnerable entrepreneurs, MLM-style
  • The zone of enoughness: how to define your minimum and maximum across money, time, schedule flexibility, and creative autonomy
  • Why “just raise your prices” might be the most misplaced advice in the industry, and what to actually do instead
  • The difference between slowing down your activity and slowing down your expectations
  • Why if your marketing isn’t working, it’s probably your market, not your mindset

Community and Reads

Seven Weeks Where Decades Happened (The Story of How My Business Nearly Went Under) | Louis Grenier

An in-depth look at someone I admire and how they 1. re-focused their business and 2. used AI to power not content, but administrative workflows.


40 Buyers and Nothing to Sell - What 9 Months of Vibe Coding Taught Me About Building With AI | Lisa Kostova

Three services doing the same job - that’s what Replit’s AI assistant had built behind the scenes. Every time I asked it to fix a broken integration, it created a new service instead of repairing the existing one. The app randomly called whichever service it reached first - like having three doors to the same room. The connection worked sometimes and failed others, for no visible reason.
There were no logs and no error messages I could see. The system broke before my debugging tools could reach it.
That’s what vibe coding at scale felt like. The system looked functional on the surface. But underneath, it was structurally broken - in ways you couldn’t see, using tools that couldn’t tell you.

Jessica Lackey

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Build your business - and your business-building intuition with foundational frameworks and practical application.


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