381: The One Strategy That Helped Me Make My First Million Dollars

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Finding the right peer group means identifying people who already have the life you want, meeting them in person rather than only following them online, and forming a small mastermind group that meets regularly. Your peers shape what you want and not just what you do, which is why the wrong group quietly redirects your goals without you noticing.

In this solo episode I explain how it took me over a decade to realize my Stanford friend group was the wrong fit for building a small business, and what changed once I found the right one.

Below is the full argument: how peers reshape your desires, why my hanky business almost died from social pressure, the conference that changed everything, and the four steps to fixing your own peer group.

Key takeaways

• Your peer group shapes your wants, not just your habits. We adopt what our friends want because it signals success in that community.
• Wrong peer group means quiet drift. My wife and I nearly shut down Bumblebee Linens because handkerchiefs were not cool to our friends.
• It took me 20 years to recognize the mismatch. Great friends can still be the wrong peers for a specific goal.
• FinCon changed everything. One conference turned both businesses into seven-figure companies.
• In-person beats following online. Virtual is a start and events are where real peer groups form.
• Mastermind groups break artificial limits. Seeing someone do it proves it is possible.
• The right group creates a new trap. You start competing on goals that are not yours.
• Make two lists. People living the life you want, and people draining your energy.

How your peer group shapes what you want

Peers change your desires rather than only your behavior, which is what makes the effect so hard to notice.

The pattern in my own life is consistent. Around someone who goes out constantly, I go out constantly, and around someone out of shape, I get out of shape.

Around someone fiercely driven to succeed, I get driven too.

The version that matters more is what I wanted after college. I wanted to work at a hot startup, drive an Audi A4 Turbo, buy a big house in Palo Alto, and own every new gadget.

None of those originated with me. Startups were what my friends were doing, the Audi was the dream car of a girl I liked, Palo Alto was where my friends wanted to live, and the gadgets came from friends who were geeks.

The mechanism is imitation as a status signal. We adopt what our peers want because those things function as markers of success inside that group, and sometimes we need someone else to want a thing before we want it.

The pandemic gave me a clean example. Every one of my friends remodeled their house, and every one of them owns a Tesla.

Why the wrong peer group stalls your business

The wrong group produces slow motivational drift rather than direct opposition, which makes it easy to miss.

When my wife and I started our handkerchief business, none of our friends thought much of it. Several questioned whether it was worth our time.

The reason is context. My Stanford friends were raising venture money to build billion-dollar companies, and a lifestyle business built around spending more time with family did not register as interesting.

The conversations sounded like this: I just raised $10 million at a $50 million post. I am pulling 80-hour weeks and we are close to a huge payout.

We considered shutting the business down several times, and the underlying reason was that a hanky business was not cool within our peer group. Sticking with it worked out, and the process was extremely lonely with nobody to share wins or failures with.

My Wife Quit Her Job hit the same wall in 2009. Nobody believed blogging could make money, so it read as a hobby and a passing fad.

The conference that changed my trajectory

FinCon is where I met the people who fundamentally changed how I thought about both businesses.

My blog was struggling for traffic and I was close to quitting. Attending my first in-person conference reversed that within days.

Three things came out of it: motivation, people to share successes and failures with, and new strategies to apply.

That peer group is directly responsible for turning Bumblebee Linens and My Wife Quit Her Job into the seven-figure businesses they are today.

The 4 steps to building the right peer group

Here is the process I would follow to fix your peer group: recognize that you have outgrown your current one, find people living the life you want, meet them in person at events, and form a mastermind group with the ones who fit.

Step 1: Recognize you have outgrown your peer group

The hardest part is admitting the mismatch, because it means accepting that people you like are not the right people for this particular goal.

It took me over a decade to see it. My friends were not bad friends, they were simply pointed somewhere I was not going.

The diagnostic signals: friends and family who are unsupportive, or who constantly question what you are doing.

The fitness version makes it concrete. If you are serious about getting in shape, stop spending your time with the friends who invite you out for dessert and boba every week.

Step 2: Find and follow people living the life you want

Identify people who already have what you are after, then break down what they actually do day to day to get it.

The internet makes this easier than it has ever been. Google, Instagram, TikTok, and YouTube all work for finding people who inspire you in a specific direction.

My own example is tennis. I follow TPA Tennis on YouTube specifically to learn the techniques professionals use.

The audience side of this is worth stating plainly. People read My Wife Quit Her Job because they want more time with family, and they have no interest in building the next billion-dollar company at the expense of the people around them. They want enough money to do what they want, when they want.

Step 3: Meet your people at in-person events

Following people online is a starting point, and in-person events are where actual peer groups form.

Nearly all of my close friends came through conferences: the Seller Summit, FinCon, Social Media Marketing World, and eCommerceFuel among others.

Most people do not know this, but I started this podcast specifically to meet people. An interview show forces me into an hour-long conversation with someone new every single week.

Step 4: Form a mastermind group

A mastermind is three to six people meeting regularly to hold each other accountable, test ideas, and push each other toward calculated risks.

Everyone in the group should want roughly the same things, since that shared direction is what makes the psychological pressure useful instead of distorting.

The real benefit is removing imagined limits. I never believed a seven-figure business was possible without a large team until I watched friends do it, and then it was obviously achievable with the right systems.

The shortcut it provides: talking to someone who has already done the thing is the fastest way to grow.

The trap of finding the right peer group

A strong peer group creates a new problem, because you start wanting what they want even when it conflicts with why you started.

Several of my ecommerce colleagues are performing exceptionally. They set ambitious goals, work relentlessly, and are rewarded accordingly.

They also do not have kids or the same priorities I have. My businesses exist so I can spend more time with my family.

I have been guilty of chasing their numbers anyway, at the cost of my health and my friendships.

No perfect peer group exists, so the work is separating your true needs from your wants. I have to remind myself regularly that I already earn more than I spend, that more money will not make me happier, and that outearning my peers is a poor use of my time and attention.

How to audit your current relationships

Open a document and build two lists: people living a life you want, and people holding you back or feeding you negativity about what you are doing.

You do not have to cut everyone on the second list. Distance yourself from the excessive negativity.

Then find where the first list gathers, meet as many of them in person as you can, and form a mastermind out of the ones who fit.

Jim Rohn’s line is the compressed version: you are the average of the five people you spend the most time with. We want what our friends want, own what they own, and chase what they have achieved.

Frequently asked questions

How does your peer group affect your success?

Peers shape what you want, not only how you behave. We adopt our friends’ goals because those goals signal success within the group. My post-college desire for a startup, an Audi, and a Palo Alto house all originated with people around me rather than with me.

How do you know if you have the wrong peer group?

Look for unsupportive reactions and constant questioning of what you are doing. The wrong group rarely opposes you directly and instead produces slow motivational drift. My wife and I nearly shut down our business because handkerchiefs were not cool to our friends.

How do you find a better peer group?

Identify people already living the life you want through Google, YouTube, Instagram, or TikTok, then meet them in person at conferences. Online following is a starting point, and events are where real relationships form.

What is a mastermind group?

Three to six people with similar goals meeting regularly to hold each other accountable, test ideas, and encourage calculated risks. The main benefit is removing imagined limits, since watching a peer accomplish something proves it is achievable.

Why are in-person events better than online communities?

Real peer relationships form face to face. Nearly all of my close friends came from conferences including the Seller Summit, FinCon, and eCommerceFuel, and those relationships turned into the mastermind groups that changed both of my businesses.

What is the downside of a highly ambitious peer group?

You start competing on goals that are not yours. Several of my ecommerce colleagues outperform me and have no kids and different priorities, and chasing their numbers has cost me health and friendships despite my businesses existing to give me family time.

How do you audit your current relationships?

Make two lists: people living a life you want, and people holding you back or giving you negative energy. You do not need to cut the second group entirely, just create distance from the excessive negativity while actively seeking out the first.