Turns Out, My Own Advice Is Really Hard to Take

Welcome back to Scaling With Soul!

We’re here to demystify entrepreneurship and make it more accessible to all.

Today we're talking about something I probably should have seen coming: the humbling experience of having to follow my own advice. For four years, I've been the person on the stage telling founders exactly what to do. Now I'm building again — my fourth company — and it turns out knowing the right thing to do and actually doing it are two completely different skills.

Before we dive into today’s topic, my next live office hours/AMA is Wednesday, March 25th at 10am PT. This is free and open to all! Join us using this link.

For the last four years, I have been that person.

The founder who sold her company, wrote the book, got on the stage, and started dispensing wisdom. Don’t raise venture money. Talk to your customers. Know your ICP. Price for value. Promote yourself. And for the love of all that is holy, do not spray and pray.

I believed every word of it. I still believe every word of it.

And now I’m building again — my fourth company, ExecutiveIQ — and I want to call my past self on the phone and say: Honey. You had absolutely no idea.

Here’s the thing about giving advice: it is infinitely easier than taking it. When I’m coaching a founder who is struggling, I can see their situation clearly. The answer is obvious to me. I say the thing with confidence and conviction, because from the outside, it is obvious.

From the inside? It is a completely different experience.

So this week, I’m pulling back the curtain. Because if I’m going to ask you to be honest about the hard stuff, I need to be honest about mine.

Here goes.

I have told founders many times, confidently: you are probably underpricing. Charge more. Price for the value you deliver, not for what you think people will pay.

NO FREE PILOTS.

Fortunately, I have a co-founder who owns pricing and can discuss it in his sleep. So ExecutiveIQ’s pricing is, in fact, appropriately confident.

But me talking about it? That’s another story.

An industry consultant approached me recently and said she wanted to propose us to some of her clients. All she needed was our pricing methodology.

Reader, I hemmed. I hawed. I was so vague I barely said anything useful at all. I wanted her engagement. I didn’t want to scare anyone off. And somewhere in the middle of my non-answer, I thought: where did the bold, confident advisor go? The one who tells founders to own their pricing? She had, apparently, left the building.

The advice is right. I just needed my co-founder to actually live it for me.

“Get out from behind your desk and talk to people.” I have written extensively about this. It is, genuinely, the single best investment of a founder’s time, and not just for customer conversations. I mean everyone. Peers. Advisors. Vendors. Other founders. People who can open a door to a game-changing vendor or refer you to a co-founder you didn’t even know you needed.

And yet, talking to people requires stepping away from your to-do list. And your to-do list, when you are building a company from scratch, is a living, breathing, multiplying organism that will consume every waking hour if you let it.

I know what I’m supposed to do. I also know how many Slack messages are waiting for me right now. These two things are in constant conflict.

I can walk any founder through ICP definition in twenty minutes.

I am genuinely better at this than I used to be. I know my ICP. I can describe them clearly.

And yet. A thought will float through my brain like a lovely balloon: what if we launched a one-seat retail model? Wouldn’t that scale beautifully? And suddenly I am mentally redesigning the entire go-to-market because the shiny object is right there and it is so…shiny.

This is where, once again, I am deeply grateful for a co-founder who has more experience at this stage than I do, who looks at me with patience and love and essentially says: put the balloon down, Sharon.

He is correct every time. That is mildly annoying and also a huge gift.

Promoting Yourself: I Am My Own Worst Case Study.

I will be honest with you. I have never been good at this. I am self-deprecating by nature. I am unpolished. I probably share truths that I shouldn’t. And I tend to understate my accomplishments. I have 80,000+ followers across platforms and I still sit on content I know is good because something in my brain says who do you think you are?

There’s more to it than that, though, and I’m going to be honest about it: I am sensitive about my age, and about the fact that I was out of the industry for four years while the world I’m re-entering kept moving. That’s pure internalized misogyny on my part. I know that, I own it, but it’s real. I feel like I’m playing catch-up. Like I have to prove I still belong, even while I’m standing on a stage telling other founders they absolutely belong.

The good news is that this one I’m working on. The bad news is it’s a work in progress.

BUT HERE IS THE BIG ONE. Some Of The Hardest Advice I Have Had To Take

The thing my entire company is built on. The principle I preach to every sales team that will listen: know your customer before you approach them. Research them. Understand what they care about. Personalize your outreach. Do not, under any circumstances, spray and pray.

ExecutiveIQ exists because we believe generic outreach is not just ineffective — it’s a waste of everyone’s time and a missed opportunity to actually connect.

So. I committed to hosting an event in New York City next month. My ICP in the room: senior leaders in corporate executive engagement — sales leaders, marketing leaders, GTM executives. Real decision-makers. The kind of people who will either become customers, refer customers, or both.

The audience quality has to be stellar. I need the right people in those seats. And here’s the catch: I don’t know a lot of these people. Not yet.

I woke up in a panic this morning and my very first instinct — my reptilian instinct — was to blast LinkedIn. Just send a message to everyone who might qualify and hope for the best. Spray and pray, baby. The very thing I have told a hundred sales teams never to do.

I almost did it. I’m not going to pretend I wasn’t tempted.

Instead, I took a breath. And then I did the thing I always tell everyone else to do.

I researched every single person individually. I wrote thoughtful, personalized messages. I referenced things that were actually true about them — one company had just posted that they were hiring an Executive Engagement lead, so I acknowledged that this was clearly a priority for them, and that perhaps they’d benefit from being in a room full of other executive engagement leaders and experts. I treated every message like it mattered. Because it did.

Did it take longer? Obviously. Did it feel overwhelming when I had fifty more names on my list and a bunch of notifications from my team that needed to be addressed? Yes. Did I understand, viscerally, why founders and sales teams reach for the spray bottle instead? Absolutely.

But that’s exactly what I’m asking my customers to let us do for them. And the moment I almost didn’t do it myself, I understood and empathized with every founder I’ve ever coached in a completely new way.

Here’s what I’ve figured out.

Giving advice activates your brain. Taking it activates your nervous system. They are not the same organ.

When I’m coaching a founder, I have no skin in the game. I have distance, pattern recognition, and zero fear of being wrong about their business. I can think clearly because nothing I say puts my own livelihood, identity, or reputation at risk.

When it’s my company? Every decision carries weight. Fear creeps in. The very human impulse to protect yourself from rejection, from failure, from looking like you don’t know what you’re doing, it kicks in hard.

I have newfound empathy for every founder I have ever advised. Not because I forgot what this felt like, but because I am living it again, right now, in real time. And I think that in the long run, having to eat my own cooking is going to make me a better, more empathetic advisor.

The advice is still good. It's just a lot easier to give than to live.

Ask me how I know.

Follow My Journey Building My Fourth Company

I have created a playlist on TikTok to document my latest startup journey. Tune in to follow along.

Sharon K. Gillenwater is a four-time founder who sold her previous company, Boardroom Insiders, for $25 million in 2022. She’s the Co-Founder and CEO of ExecutiveIQ, an executive engagement platform for go-to-market teams. Follow her journey on TikTok and LinkedIn, and subscribe to her newsletter Scaling With Soul.

Ask Me Anything: Got a burning question about building or scaling your business? Drop me a line at sharon@sharonkgillenwater.com. I personally read every email and respond to as many as possible. The most interesting questions might be featured in future issues (with your permission, of course). No question is too basic or too complex—I'm here to help you succeed!