The most common question I get: HOW are you starting and running so many businesses simultaneously?!

The short answer is: I’m not. I’ve partnered with a bunch of incredible people to bring these organizations to life.

The next question is: “Fine, but how does it all actually work? How do you interact and lead these people?”

“Well…uhhh…where do I start?”

I finally have a good answer and it's in this email.

Today, I’m doing something very different.

I invited my friend Andrew Warner to write this email. He interviewed all my partners and wrote up their stories about how I lead.

Here’s what he learned:

I insist that my companies’ leaders use Superhuman for their email because: Built for speed: Fast search. Keyboard shortcuts. Well-placed buttons. AI responses: It uses YOUR writing style to suggest AI responses to inbound emails. Summaries: With one keypress, it summarizes long emails into short bullet points. Exclusive offer to my readers: First 200 readers to click here get 1 free month

Jesse doesn't do your work.

On a flight to meet one of our first clients, I opened the 100-page presentation my team and I put together and saw Jesse's notes.

The whole thing was marked up with questions and suggestions, like these:

And on and on.

He seemed to have over 200 suggestions. It probably took him longer to make those comments than to just fix the deck.

Honestly, I was frustrated with Jesse. He's a former McKinsey consultant. Why didn't he just make the changes himself?

That night, I spent 4 hours reworking the presentation based on his notes.

Then, I got up at 4:30am the next day and continued working on it.

I spent 8 hours making changes he could have made in 1, but his feedback was right.

The presentation went well because of the changes he recommended.

Looking back, I understand why he leads this way. After doing all that work on that project, I never look at a presentation deck the same way again.

Now I immediately think "How do I turn this slide into 1 clear point?" and "Where's the 'so what?'"

Doing it myself really mattered.

Jesse is very candid.

Three months after working with him, Jesse looked at me and said, “You have a confidence problem.”

He wasn't being cruel.

He also told me that I'm one of the most talented people he worked with. But what he said about my confidence struck a chord.

It’s something I wrestled with in my life and career. I’m an organizer. I excel at marshaling processes and people.

What accompanies that is my peacemaking personality. When I build consensus, I tend to lose my own voice.

At my last company, I was on the leadership team when I was told to push a new, aggressive pricing structure on our clients.

I disagreed with it, but I avoided conflict and didn’t speak up. Instead, I did what I always do: I got the job done. I made it work.

Even though I disagreed with the decision. It was one of many small "cuts" that led me to break from the company.

By speaking candidly about my confidence, Jesse was encouraging me to notice and break my pattern.

He didn’t want me to shut up and get the job done at Gateway X. He wanted me to be a better person through Gateway X.

Sometime after he challenged me, I helped make a key hire at one of our portfolio companies.

She was someone I deeply respected and had a personal relationship with. Unfortunately, we had to close down the company and part ways.

Left to my old ways, I wouldn’t have had the confidence to speak up and say that I wanted her to be treated well on the way out and to participate in deciding how to do that.

I might have grown resentful and been reluctant to bring other people who mattered to me into the company.

Instead, when we closed down the company, I helped create as supportive an exit for her as possible.

Jesse leads by coaching the "whole person."

I was in a planning session with one of our CEOs. I could tell the CEO wasn't fully on board with the plan he was setting for us.

But I thought to myself, This is the plan. Ok. Time to execute.

While Shonak, our COO, and I started talking about how to execute, Jesse was just listening.

Then Jesse started doing some of the coaching work you read about in previous editions of this newsletter (like checking for alignment between the CEO's head and heart) and some of the Conscious Leadership Group techniques we use to guide our companies (e.g., was the CEO "above the line or below the line").

This was new to me. In a previous company I worked for there was someone in management who was full of misalignments.

He was leading projects he wasn't right for.

As new people discovered it, they kept leaving his department, but he stayed, costing the company money and wasting resources.

All because nobody took the time to consider him, the person behind the job title.

Needless to say, after Jesse's coaching session, CEO's plan was scrapped. We didn't burn time on it.

When I started working at Gateway X, I knew that personal development was important here.

I'd been given a coach that I could talk through anything with. The more I work here the more I see the impact of that on the company.

We're all aligned. We work together more cohesively than any team I've been on.

Jesse leads through mentorship.

Before leading Unbloat, I was doing part-time contract work at Gateway X for three months.

Jesse called me every single day.

He asked about the work I did, or told me about what was going on at one of the Gateway X companies, or just checked in on my life.

Then he surprised me by asking me to join Gateway X, full-time.

I called my sister for advice. I told her that I was planning on taking time off after closing my previous company.

When she heard how supportive Jesse was over my 3-month engagement, she said, "Carolyn, the best thing you can do is find a mentor who really cares about you and wants to see you grow."

I joined Gateway X and became CEO of Unbloat.

That November, Jesse and I were looking at our Facebook ad performance.

He could tell I didn't understand the metrics, how they influenced sales, or how the contractor we worked with organized everything.

But Jesse looked at me and said, "Starting December 1, you're going to take over our Facebook account."

Within days I was in charge of a $40,000 monthly budget.

I never even launched an ad before, but Jesse believed I could do it, so I prepared. I watched YouTube videos.

I asked experienced advertisers to audit our account. I got friends to show me how to set up audiences.

I did everything I could to get up to speed.

I ran the Unbloat Facebook account for 5 months. I improved our ads' performance.

It wasn't the most efficient growth, but by the time I hired a Facebook ad manager, I understood exactly what to look for, what questions to ask, and how to run a profitable ad campaign.

What gave me the confidence to figure it out was knowing that Jesse understood me and wouldn't have put this responsibility in my lap if he didn't know I could figure it out.

This is what my sister was referring to when she advised me to work with a mentor who cared about me and wanted to see me grow.

​

Jesse leads with culture.

My relationship with Jesse goes way back. In high school we were both on an executive board, working on a school float.

If I'm honest, at the time I was bothered by his attitude on that project.

I was the coordinator, making sure everything was getting done, meanwhile he was just chatting and having fun with everyone.

Later, I realized that Jesse was creating an engaging atmosphere that volunteers wanted to be in.

Fast forward to our work at GrowthAssistant where we planned an offsite after we staffed up.

I told him I was preparing to talk about all the initiatives we were going to run, and expected inputs and output.

I went down my prep list with him, Jesse slowed down and said, "How about values?" It's a "very Jesse" topic to think about.

He ended up leading a workshop on that at the retreat.

Today, values are a key part of how we all work together at GrowthAssistant. For example, a while back, one of our salespeople was on a call with a major prospect.

He sensed that the deal wasn't going to get wrapped up unless he did something outside of our normal offering.

He could have stopped and sought approval for his idea, which might have stopped the deal's momentum.

Instead, the salesperson knew that one of our key values is to "move fast, move forward, learn things."

So he offered the prospect a discount and closed the deal. What's important to notice is that he didn't just move fast and move forward with the deal, he also made sure the organization learned from his experience.

Today that type of temporary discount is part of how we close big deals.

We have a #kudos channel in our Slack where anyone can compliment team members who live our values.

It's how we create an environment that's as rewarding as building the high school float was.