In this inspiring episode of the #WisdomOfWomen Show, I sit down with Sharon Gillenwater — co-founder and former CEO of Boardroom Insiders, a SaaS business intelligence platform she bootstrapped, scaled, and sold for $25 million — all without a single dollar of venture capital.

From waitress to exited tech entrepreneur, Sharon’s journey challenges Silicon Valley’s myth of what success must look like. She shares her three defining life moments, the heartbreak of a failed first startup, and the radical lessons that led her to build a profitable, purpose-driven company rooted in integrity, empathy, and courage.

You’ll learn how to trust your instincts over conventional wisdom, lead with heart, and grow your business without selling your soul. Sharon’s story is a masterclass in grit, grace, and grounded wisdom — and a roadmap for founders who want to do business differently.

Key Takeaways:

• Profitability and purpose aren’t opposites — they’re partners in sustainable growth.
• “Employee-first” leadership is the most effective customer strategy.
• Bootstrapping builds discipline, freedom, and true wealth.
• Founders must make every decision defensible — with clarity, not convention.
• Being someone’s first customer can forge partnerships that last for years.
• The best exits are built from day one: clean books, lean ops, clear leadership.
• Empathy and usefulness are a founder’s most underrated superpowers.
• Failure is not the end; it’s the foundation of your next great success.

Chapters:

00:00 – Welcome & Introduction

06:00 – Three Life Moments That Shaped Her Path

12:00 – The Dark Side of Venture Capital

15:00 – Rebuilding from the Ground Up

18:00 – Bootstrapping and Seed-Strapping

24:00 – Building the Tech Without a Tech Background

28:00 – The Art of the Exit

32:00 – Life After Exit & The Next Chapter

38:00 – Scaling with Soul Today

43:00 – Rapid Fire Round

Burning Questions Answered:

1.What really happens when you raise venture capital — and why might it kill your company?

2.Why is “employee-first” leadership the ultimate customer strategy?

3.How can founders recover from failure and rebuild stronger?

4.What does it really take to prepare for an exit that leaves you proud—and paid?

Favorite Quotes:

“You have to be in love with the problem, not the solution.”

“Put employees first—because they take care of your customers.”

“You can fail spectacularly—and still rise again.”

Guest Offers & Contact Information:

www.sharonkgillenwater.com

https://substack.com/@scalingwithsoul

https://www.tiktok.com/@sharonkgillenwater

https://www.linkedin.com/in/sharonkgillenwater/

https://www.youtube.com/@sharonkgillenwater/shorts

Buy Sharon’s book, Scaling with Soul:  How I Built and Sold a $25 Million Tech Company Without Being an A**hole

From Women-Owned Bookstore:  https://bookshop.org/p/books/scaling-with-soul-how-i-built-and-sold-a-25-million-tech-company-without-being-an-a-hole-sharon-k-gillenwater/21496638?ean=9781964377018&next=t

From Amazon:  https://a.co/d/9LTOM4u

Follow the #WisdomOfWomen show for more inspiring stories and insights from trailblazing women founders, investors, and experts in growth and prosperity.

YouTube: https://tinyurl.com/yja3w7nh

Spotify: https://tinyurl.com/4tak8ajk 

Amazon Prime: https://tinyurl.com/366syddj 

Apple Podcasts: https://tinyurl.com/bdhananz 

RSS Feed: https://feeds.captivate.fm/womengetfunded/ 

Coco Sellman, the host of #WisdomOfWomen, believes business is a force for good, especially with visionary women at the helm. With over 25 years of entrepreneurial experience, she has launched five companies and guided over 500 startups. As Founder & CEO of A Force for Good, Coco supports purpose-driven women founders in unlocking exponential growth and prosperity. Her recent venture, Allumé Home Care, reached eight-figure revenues and seven-figure profits in just four years before a successful exit in 2024. A venture investor and board director, Coco’s upcoming book, *A Force for Good*, reveals a roadmap for women to lead high-impact, high-growth companies.

Learn more about A Force for Good:

Website: https://aforceforgood.biz/ 

Are Your GROWING or PLATEAUING? https://aforceforgood.biz/quiz/

FFG Tool of the Week: https://aforceforgood.biz/weekly-tool/ 

The Book:  https://aforceforgood.biz/book/ 

Growth Accelerator: https://aforceforgood.biz/accelerator/

Welcome to the Wisdom of Women Show.

We are dedicated to amplifying the voice of women in business.

A new model of leadership is emerging and we are here to amplify the voices of women leading the way.

I am your host Coco Selman, five time founder, impact investor and creator of the Force for Good System.

Thank you for joining us today as we illuminate the path to unlocking opportunities and prosperity for women led enterprises by amplifying the voice and wisdom of women.

Today we have a glass breaking trailblazer in our midst.

Sharon Gillenwater is the co founder and former CEO of Boardroom Insiders, a SaaS business intelligence company.

She bootstrapped, scaled and sold for 25 million without outside funding providing, proving that profitability and values can grow together.

Today she is the author of Scaling with Soul, How I Built and sold a $25 million tech company without Being an a Hole where she shares her journey from waitress to exited tech entrepreneur.

Offering both practical strategy and raw lessons in resilience.

Through her company Scaling With Soul, her book and fast growing TikTok platform, Sharon is on a mission to make entrepreneurship more accessible, humane and wildly successful for founders everywhere.

Welcome Sharon.

Thank you for having me Coco.

It's such a pleasure to have you and be with you.

I know we're together in the whisper group, right, which Carrie Kirpin has founded and I've gotten to know you through that community and it's been such a pleasure.

So what was a book written by a woman that has significantly influenced your life?

Now this is a little book that no one will probably have heard of, but if you are an entrepreneur, particularly a woman entrepreneur who was never part of the club in terms of being able to raise venture and you know, going to the right schools, I would highly recommend it.

It's called Lunch with Lucy by Sherry Stuart Deutschman.

I believe she self published this book.

Not only did the book have an impact on me, but Sherry was one of the first people I spoke with after I exited my company.

When I sold my company, I had no idea that it was a big deal what I did.

I thought, you know, because I live in the Bay Area and it just seems like everyone's doing this.

A friend introduced me to Sheri and we talked on the phone.

She said, you have no idea how rare your accomplishment is and you need to get out there and talk about it to help other people do the same Thing, it stunned me and I started looking into the statistics of exited entrepreneurs, particularly women exited entrepreneurs, particularly bootstrapped women.

I discovered she was right.

I bought her book and I read it in about eight hours or less.

I laughed, I cried.

There were a couple of takeaways from it.

The first was that she said, you know, everyone says put the customer first, but she said, that's not right.

What you do is you put the employees first because if you put the employees first, they are going to take care of your customers.

And I loved that and I think about that all the time.

And the second thing that she did, the title Lunch with Lucy comes from a thing that she did at her company.

She comes from nothing.

She was married off at 17 or something and had to leave her husband and had two kids on her own.

And she's a self made woman.

When she was running her company, she realized that as the CEO that people might not tell her the truth about certain things or she might become more removed about what's really going on and their problems might develop in the company that she doesn't know about.

And if she doesn't know about it, she can't address it.

And so she would pick one employee every week and take them to lunch.

She would explain to them, I'm not Sherry, the CEO while we're at lunch.

I'm your coworker, Lucy, and I want you to talk to me just like you talk to a coworker.

And I want to really hear what your experience is like.

And so that's where the title comes from.

And it's a wonderful book.

It has so much heart and shows as a CEO and a founder, what heart and integrity she had.

I found it very inspiring and I would recommend it to any entrepreneurs.

Oh my goodness, I can't wait to read it.

It sounds, you know, I fully agree with the idea, the notion of an employee first approach, right.

Like that's your first customer in my mind.

It's always been in my mind.

Thank you for that.

That's a wonderful recommendation and I'm sure we'll all go pick it up.

Some of the wisdom from Sherry in Lunch with Lucy.

I love that.

So, you know, I.

One of the, what I like to do at the beginning of every interview is hear about you and your life so that we understand you as a human.

First, I invite you to consider three moments in your life that create the arc of your story.

Three moments that have shaped who you are.

They can be personal moments, they can be family moments, they can be moments in in your business or your your development professionally.

But three bold moments that shaped your life.

What would those be?

Well, early on, in my first real job, I worked at a magazine, San Diego Magazine.

I worked there, and there were two women who were my mentors.

They were the two leading editors there, and they were fantastic and I respected them so much.

One of them, Ginny Butterfield, one day said, I'd like you to go to the local bookstore and buy a couple of books for our interns as departing gifts.

Just buy two of the same book, but find a good book about writing or editing.

So I went to the bookstore.

I got these books that looked interesting to me.

I came back and I put them on her desk so she could sign them for the interns.

She came into my office looking down at me over her glasses.

She said, did you happen to peruse these books at all?

I said, I looked at the dust jacket and she opens one of the chapters and it says, why your editor is an idiot.

It was just a little moment.

But one of the things that taught me is for every decision you make at work, it has to be defensible.

You have to be able to defend it and explain why you did that thing.

And I've learned that lesson a few times, but that's the first time I can remember doing it.

The principle of defensibility has been a common thread through all of the work that I've done since.

And at Boardroom Insiders, it was something that I preached to our editorial team because what we were doing was quite subjective and it was very high value for our customers, telling our customers what was most important to their C suite customers.

And I said, look, we're making choices.

We're curating content here.

And if we ever get a question from a customer, we have to be able to defend what why something is or is not in our profile.

And so that became a hallmark of Boardroom Insiders too.

Whatever I'm working on, I want to be able to go to the mat to defend it with my own experience, regarded incredible sources and all of the things.

So that was a big moment for me.

I think the second moment was I was floundering around in San Diego, not after that job.

I was freelance writing.

I wasn't making any money.

I went to grad school because I didn't know what else to do.

I came from a blue collar family and my parents didn't go to college, so I didn't understand how to navigate looking for an office type job.

I got married and I moved to San Francisco, which is a place I had always wanted to live.

When I went to San Francisco, I immediately started applying at all the big corporations there.

Gap, Levi's, Williams, Sonoma.

And they just were not interested in me.

I could not get past the first interview.

For whatever reason.

I was referred to a friend of a friend who had a startup, and she hired me on the spot to be in sales, which I had no experience doing.

But I think she could see that I was eager to learn and excited about their business.

And I was a Swiss army knife.

I could do a lot of different things.

Maybe that's why the corporates wouldn't want to hire me, because I wasn't focused enough in my experience.

And she saw me as somebody who could just get in there and do lots of different things.

It was a revelation to me.

And I got into the startup world and I never left.

That's what I love about startups, is it doesn't matter.

Given my background, I don't have the pedigree that a lot of people in business do, from neither the family pedigree nor the educational pedigree or the connections.

But if you go into a startup, they don't care.

They don't care where you came from, who you know, or where you went to school.

It's like, how can you get stuff done well and can you get it done fast?

And if you can do that, you will become a leader in the company in no time and you will just learn a ton.

And so that was probably the second major milestone for me, career wise.

And then I think the third one was a big failure that I had.

When I my first startup, I was in San Francisco in the middle of the whole dot com thing.

In the late 90s, I started a company and I listened to what, you know, conventional wisdom and experts said.

And the things they said is, you are not bona fide if you don't raise venture capital, so you have to raise venture capital.

I raised venture capital and it killed the company.

It literally killed the company.

Because when the NASDAQ crashed and everybody was panicking, including my investors, they fired their CEO, the firm that funded us, and they had all these content companies in their portfolio and they decided they were going to pivot to biotech.

And so they wanted out of our deal.

They couldn't legally get out of the deal because we had a deal.

But I always tell this to people, if they want out, they will get out.

And in our case, they filed a sham lawsuit.

They accused us of fraud, which we were not committing fraud.

But they had all the lawyers and all the money.

And so it forced us into a settlement and they got the majority of their money back.

And so that was the beginning.

For the rest of my life, I don't trust conventional wisdom.

I don't trust what the insiders say.

I think it's all bullshit.

It works for the people who are in the club, but it doesn't work for the rest of us.

For the most part, there's a lot of posturing and people not really being honest about what these funding situations look like and how it impacts your exit.

I'm trying to blow the whistle on all of that because the reality is most venture backed founders who exit walk away with an embarrassingly low amount of money, way less than I did, in fact, on a $25 million exit.

And I found this out when I started sharing my own numbers.

It has instilled in me a distrust of conventional wisdom of all kinds of.

And it has made me really value the perspective of outsiders.

It's given me the confidence to do things differently and follow my instincts and most importantly, always put my customers first and listen to them and not listen to all these so called Silicon Valley experts because they can really steer you in the wrong direction.

Wow, those are three really powerful moments.

This last one here, we'll get into more because I want to hear what happened next.

You decided to keep going.

What I find remarkable, and I'm sure our listeners are thinking the same thing, you could go through that and not just be like, I'm done, right?

You decided to keep going, which I think is the mark of a true entrepreneur.

You just, you just keep going.

Like you can't almost help yourself.

And so how did you move from that failure to continue on and eventually create this incredible tech company, Boardroom Insiders?

Well, there were a few more important events that happened.

I was right.

When fidget.com failed, that's the first company.

I was in the middle of that crazy period where you're starting to have babies.

I had a baby when I created Fidget and then I had another baby after it failed.

That's all kind of a blur that whole period.

And then 911 happened after the dot bomb happened, you know, a year, a year and a half apart.

And in San Francisco, things just weren't coming back.

And so I had to take a job.

That was the worst job I ever had.

It was just horrendous.

And I write about it in the book, like unbelievably so.

And I worked there for six months and then I decided I am never going to work for anyone again.

And that pushed me back into entrepreneurship.

When you make a decision like that, the first thing that you do is you contact everyone you know and say, I'm going out on my own to do what.

Here are the things that I can do that I'm good at.

If there's any way I can help you with any projects in the short term, let me know.

I made private label pasta sauce in my kitchen.

I did PR for an aircraft carrier museum.

I did all kinds of crazy things.

A friend of mine who I had worked with before, he actually was my assistant when I was at that first startup.

And while I was having babies, he was climbing the ladder in tech marketing.

He called me and he said, you got to come work with me on this project for Intel.

I said, I don't know anything about intel or tech.

He said, no, you're going to be great.

I know you can do it.

That kicked off nearly a decade of consulting with tech marketers.

The more I saw of tech marketing, the more I realized they had in big tech the same problem, which was these deals were getting bigger and bigger.

Eight figures, nine figures.

And pretty soon the CEOs of big enterprises are saying, what the heck is this technology we're buying and what is it going to do for us?

Because it's very expensive and it's going to be touching every corner of our organization, and we want to understand what it is.

So the big tech sales reps were being called into C suites at their customers, and they were shaking in their boots.

I didn't know how to shift from talking about hardware and software and features to business impact.

So I created these dossiers on these Fortune 500 execs for sales prep.

And I did them bespoke for a long time for a lot of my customers, and they would pay a lot for them.

They had relationship maps like, how are we as a company connected to this executive?

Then I thought, I should just put all these in a database and create a subscription database product.

And so that was the genesis of boardroom insiders.

I spent a number of years weaning my clients off of my consulting services and moving them over to a SaaS product.

And so that took quite a while, but it worked.

It worked.

It was a slow ramp.

We were ahead of the market because just because Cisco, VMware, sun and Oracle are doing this kind of approach, it doesn't mean that the next level of companies down are clued into it yet.

And so you built us, as you said before, and you talk about in your book, you built this bootstrapped, right?

So you did the consulting and used that revenue.

Tell us about how you funded it and when you got advice from others and how you got tech people, how.

You learned about that.

I wasn't very disciplined in the beginning about keeping track of what money I was putting into the product.

I kind of thought of it as one big thing.

I operated the two of them side by side, and everything was bespoke for a number of years, even though I was putting everything in a database.

But the customers weren't really using the database that much at all.

They would come to me.

The first customer, essentially, you were using.

I was using it for my own consulting, and it was clunky and ugly, but I eventually got a few customers in there using it.

They would ask, do you have this profile?

No, but I'll create it for you.

I was populating the database almost like if you think of a staircase and you're putting each stair down as the customer's going up.

There were times when I was very transparent about that, and then there were times that I just completely lied.

Somebody would call me, a net new person who I didn't know, and they'd say, oh, I found your product on the Internet and this looks amazing.

Do you have a profile of X person?

And I'd be like, yeah, we do have that.

It hasn't been refreshed in a couple of months, so if you wouldn't mind, give my team just overnight and I'll get it to you in the morning.

And then I would create it from scratch overnight.

My husband and I would stay up all night creating these profiles and then they would love them.

And so it gave me a way to test the market and see do people find these useful?

What are they using it for?

There were use cases that had never occurred to me.

Kind of ancient, outside of my ideal customer profile.

But I learned a lot, and that's with.

With the funding.

So I would use that funding to keep enhancing the product.

But at a certain point, I knew I've got to separate these two things.

And I really hadn't kept track of how much money I put in, but I put down on the.

On the financials.

It was like 42k I put in, and guess what?

That 42k was still on our financials when we sold.

And the buyer Was like, what is this?

And it's really the only thing on there that wasn't completely buttoned up.

And I had to explain, well, you know, I just kind of paid for stuff in the beginning.

Beginning.

And so this was on our.

What is it?

A balance sheet.

My balance sheet.

What the buyer did is they wrote me a separate check for that amount.

That's amazing, right?

I did.

To your point, we were bootstrapped.

However, I think technically the term that we would use now is seed strapped.

Very different.

Yeah, yeah.

And it was just convertible notes.

They converted after 10 years right before we sold.

It was very clean.

They were hands off angels.

But they all are seasoned entrepreneurs themselves.

So they offered advice from time to time, became personal friends and respected colleagues.

So that's what I always recommend.

Bootstrapping.

Unless you can get to profitability very, very quickly and you have a high margin, low cost, it's difficult.

Or you have a spouse who's supporting the family.

I didn't have that.

My husband was the stay at home parent.

He worked a little bit, but I needed to bring in income.

We did get to profitability quickly, but I didn't pay myself from that business for four years.

I kept consulting on the side to support my family, you know, whatever it takes.

And given the experience I had, not only with my first startup and venture capital kind of putting the kibosh on it, plus that terrible job I had that I never wanted to work for anyone again, I was very determined to make it work.

It all worked out.

We kept everything very lean.

And then at a certain point we were paying ourselves quite well and we could have just kept going like that, but we decided to sell for a number of different reasons.

So it was a tech company you worked with, you found some developers and kind of figured it out that way.

Just as the jack of all trades.

What was the term you used before the utility knife.

You were able to sort of figure this out, right?

Well, I'm a non technical founder and my partner was also a non technical founder.

I guess a risky decision to bring on another non technical founder, but he was very strong in sales, customer relationships and finance and I needed all of those things.

And so we limped along for quite a few years with a series of Developers.

I mean, it was very basic.

It didn't even have a good admin where you could manage customers and see what customers were doing.

None of that.

It was just the database and logins and the ability to input new content.

And that was developed in India and that was a terrible experience.

One of my content vendors found me a guy in Texas who did new php.

Really cool guy.

He had a full time job, so he moonlighted on the side for years.

That's all we needed.

But then when we had some real users, we outgrew him.

I tell founders this is a normal thing to happen when you're bootstrapping.

You don't want to over lawyer yourself.

You don't want to over index on C level people in your own company.

You don't want to overspend on a big web development firm.

You can't do that.

You just, you're going to waste too much money too early before you even really know who your ICP is, what customers really are looking for.

You have to hold back and be shitty, have your product be shitty while you learn.

And then at a certain point we outgrow the single guy in Austin, right?

And then we went looking for.

I remember we were going to redo a filtered search.

We had all these ideas for new filters and customers were requesting.

So we found a firm in Charlotte that redid our filtered search and it was a nightmare.

They sold us the A team and gave us the D team.

Like people who were literally learning on the job.

My partner and I had to test every round.

Every time they pushed out a new version, we had to do the testing and there would be bugs everywhere.

And I mean, I'm not that, I'm not a detail person like that to sit and comb through a piece of software, test every feature and write down what's happening.

It was a nightmare for me.

In the end it worked out.

We got a vastly improved filtered search and they only charged us $13,000 because they screwed it up so bad.

And then we finally found our development firm that we stayed with for years and we just loved.

They're called Dual Boot Partners and we were their first customer.

I realized when I was writing my book and starting to tell my story, I realized that twice I was the first customer of two different firms.

And not only did it work out amazing because you get all kinds of special attention from the founders, they are determined that you are going to have a killer experience and you grow as they grow and you grow as founders together and you have this special relationship.

The other firm was our research firm out of India and they were amazing.

We were their first customer too.

I always tell people, don't be afraid to be someone's first customer.

There are a lot of advantages to it.

You're going to get a lot of extra stuff for free because they are going to work like hell to make sure that you have a good experience and a good outcome.

They need that to succeed.

That's amazing.

I agree with you.

There's a lot of value in finding those right people.

I found that when picking different partners, a lot of times the bigger, more reputable ones just don't care about you as a tiny entity getting started.

And I found so much more positive experience or it was just so out of touch expensive that I couldn't get really what I needed.

I would take the tiniest option available and I really needed more, but I couldn't afford it.

So I love this.

So tell us about your so you exited and what was that like?

It was a lot of fun.

It was exciting.

It was new.

I've never done anything like that before and I had to learn it as I was doing was stressful, but I thought it was very exciting and I learned so much.

I thought, well, it's too bad I'm not going to do this again because there are some things that I would do differently.

There's some things that I know and I'm a lot more confident around now that I've done it once.

That's why I like to talk about it.

I was on a webinar yesterday.

In fact, I'm doing two webinars within a week about how to exit and what my experience was like.

I wrote a substack newsletter yesterday which was published last night about exiting and the things you need to think about, what buyers care about.

There's just so much that I learned that founders need to know.

Yes.

I felt the same way going through my exit.

Things that I wish I'd known from the beginning I would have established earlier on.

They don't want to hear that you're the most important thing in the business.

That's not what they want to hear.

They don't want to hear that you work so hard and everything revolves around you.

They don't, you know, they do not.

Right.

They want to know that the business can function beautifully without you.

And you know, and then that due diligence I know you went through a lot with the due diligence process.

How long did that take you?

The whole deal from start to finish was about four months, which is very quick.

That's fast.

I think the fact that our cap table was just so simple and that felt great.

Also.

We didn't have any skeletons in the closet.

No lawsuits, security breaches or privacy problems.

Everything was very clean.

I remember that because I. I was like, okay, they're.

I thought the lawyers would start after Thanksgiving.

They literally started like Thanksgiving Day.

I was getting emails from employers.

And then we closed Due diligence right up until the very last day.

We were still providing documents and things.

And we closed, I think January 20th or 21st of the following year.

So due diligence was about two months.

That's actually amazing.

It sounds like you came through it pretty unscathed.

Did you sell everything all at once or did you stay involved with the company or did you sell and you were done?

We sold and then did some consulting for like three weeks.

They gave me and my partner three month consulting agreements, but we were done in three weeks.

They weren't asking us for anything more.

I remember because it was my birthday, February 25th.

That was kind of the last time I went on a meeting.

And that was it.

Right.

How do you feel now, now that it's passed?

I'm glad that I did it.

I'm astonished at how well it went and how well we did with the terms of the deal.

Based on what I know now, we were lucky.

And we also had an amazing team helping us on due diligence.

Dual Boots supported us throughout due diligence, as did our fractional cfo.

They were on our due diligence team and leading those conversations about infosecurity, our tech stack, or our financial model.

They talked the buyer through those things, so I would definitely do it that way again.

I shared with you before we started recording that there's been a new development in the last few weeks.

A few weeks ago, I learned from people who used to work for me that the private equity firm that owns the company now, the first company that bought it, packaged it up with some other products and sold it to private equity.

A few weeks ago, they just without any warning, announced they were shutting down Boardroom Insiders, the product and the company, and they laid off more than half the team that day.

They've kept on a skeleton crew to keep servicing customers and they did not tell any customers.

So I offered to buy the company back.

I made a couple of different offers and I met with the private equity firm and they do not seem interested in selling it to me or anybody else.

That tells me there's something going on that.

More missing some information.

They might be in the process of divesting assets themselves and they might want to write this off.

I don't really understand how private equity works, but now I am considering whether I should rebuild the product as a native AI product.

The product, as good as it was, had some scalability issues.

Something that deep and with that much information per record is hard to scale, and it was highly curated by experienced business analysts.

But now with AI, that scalability problem could go away.

It could be a product for a much broader audience, not just enterprise.

And it could run with a much smaller team and have enhanced features like AI agents that help the customer configure their data exports in a way that matches up with a piece of data they have internally.

That's one of the things I've talked to customers about.

I've made a TikTok about this, and I've gotten incredible feedback from people who have ideas for how I could do this.

I'm considering it, but I'm 60 years old and I'm like, man, you know, is this.

Do I want to do this?

Why am I doing this?

Am I doing this because someone's trying to kill my baby?

Am I doing this because I like making TikTok videos and sharing what I'm doing?

Am I doing it for the content?

Am I doing it to rescue the team that I love so much that used to work for me?

You have to think of all these things, and what I've learned from writing a book is you don't know what's happening when you're in it.

You don't realize why you're doing what you're doing until later, until you can reflect back?

So I'm under no illusions that I have clarity about where my head is at right now.

I'm proceeding with caution and talking to a lot of people.

I'm talking to customers, industry experts, AI experts and product experts.

I have a quote from Dual Boot, who built the first product.

And the world has changed so much.

One of the things that I've proposed to them is I've built this huge following on TikTok.

Now let's do a building in public.

Let's talk about.

We're getting the band back together.

We're rebuilding the same product with AI.

And, you know, and.

And one thing I want to talk about is I was the first customer of Dual Boot.

Now they're like a 16, 20 million dollars company.

And is it going to be the same experience working with them as it was the first time I'm getting the same team?

I mean, it's like so real synergy.

And fun in that.

And I think also I've watched you, right, since I've gotten to know you.

I've been watching you on your socials and on your Substack channel.

I would say you are embracing your journey and sharing your wisdom.

And from what I can see, you're having fun.

Oh, yeah.

I love being you.

Other people, to me, it's so satisfying that you can help other people.

That's why I mentioned Sherry Deutschman in the beginning, because she's the first one who told me.

She's like, girl, this is a big deal.

You have stuff that people need to know and they don't know.

And I said, are you sure?

Doesn't everybody know all this stuff?

And she's like, no, you need to get out and talk about it.

It's going to help so many people.

And it wasn't until I started talking to other entrepreneurs that I realized, oh, this does seem to be helping people.

Yeah.

Well, I'm excited to see how this all unfolds and tell us a little bit more about your current business.

You have your book and.

Tell us.

About that endeavor, that business, and how can people learn more about that?

Well, the book, it all started with the book and telling that story.

I enjoy writing.

I started my career at magazine writing and have expanded the Scaling with Soul brand into a Scaling with Soul substack newsletter.

It's more of a how to for entrepreneurs, supported by stories from my own experience or the experiences of people I know.

For example, this week the article is all about how to exit like a boss and all the things you need to think about from the start when you start your business to have a smoother exit.

One of the things I write about in this article is a simple thing you can do.

Just listen to the side conversations that are happening.

When you're in a due diligence meeting or a meeting with your banker or buyer, people are talking and having side conversations and you can get a lot out of those side conversations.

Stuff that I heard inside conversations allowed me to go back and ask for 50% more money.

I didn't get the 50%, but I got 33% more than the original offer.

And it was all because my wheels started turning based on what I heard when people Were just talking on a zoom before the meeting started.

So the substack is supported by other Stories and it's a free newsletter.

If you subscribe and pay 10 bucks a month, you can come to my office hours, which happen two to four times a month.

And that is a great little community that the same people, core people, tend to show up.

And there are some very smart entrepreneurs who show up.

And so it's become more of a peer coaching kind of situation.

It's not just me because I don't know everything.

And so there are other people on there who everybody's helping each other, and so I enjoy that a lot.

The other thing I'm working on is developing a keynote.

I do a lot of speaking.

I do fireside chats and everything.

I'm developing a keynote with a training organization called Heroic Public Speaking.

I'm seeing if I can turn myself into a keynote speaker and make money doing that.

Everything I'm doing now, you know, it's.

It's.

I have little revenue.

I have.

It's.

It's really funny.

People who do what I do have seven or eight different revenue streams.

And at any given time, you may not be sure exactly what they are, but you just see these checks come in through your bank account.

You're like, is that my book revenue or is that my substack revenue, or is that my TikTok revenue or my YouTube revenue?

It doesn't add up to a lot, but I'm having fun doing what I'm doing and I'm learning.

I would love to build a bigger business out of what I'm doing, but if I don't, that's okay too.

I'm just enjoying it.

I'm trying to crack that code.

I understand standing at the 50,000 foot level and seeing your whole story as you've just sort of peppered your life and told us about you.

There could be this wonderful alignment where you continue to serve the same audience that you're serving right now and build another tech platform, do it publicly and allow people to see you make those decisions.

And, you know, because it's.

It's hard.

I always say to everybody, like, you know, that I.

All the founders I talk to.

Every time you build a new company, yes, you get better at understanding the mechanics of what makes the flywheel spin.

But you still have to crack the code.

You still have to understand your market.

You still have to understand the product.

You have to still understand what the problem is you're solving.

And it's a unique experience every time.

Starting A new business every time.

Very different.

That's what I think about when I think about counseling entrepreneurs.

I remember talking to my husband, and I said, this whole thing I'm doing, I figure it has a shelf life of about three years.

If I'm not building anything, my advice is going to lose relevance.

I had a boss at that first startup.

She left the company when I started my company.

I would go to her for advice about three to four years in from when she left.

I was talking to her, and I realized she doesn't really know how things are working now, what's going on.

And I thought, that's gonna happen to me.

If I dive back in, I'll have that going for me.

But there's a lot of fear with doing this.

First of all, I'm not as hungry as I was, so I'm like, will I work as hard?

Will I push myself as hard?

Maybe I don't need to, because I was doing it on my own before, and now I would have a team.

And then the other fear is like, well, I'm gonna be doing this in public.

What if I fail spectacularly?

And then everyone's gonna know and see it.

I'm 60 years old.

Like, I'm kind of beyond.

I'm too old to care really that much about it.

I care, but I'm not as prideful as I was earlier.

I'm more humble because I've failed and I've succeeded, and I'll fail and succeed again with what I'm doing over the past three years.

I was going to launch this course, and then halfway through it, I'm like, I don't enjoy this at all.

I like the exchange with people.

I don't like sitting, talking to a camera.

And so I just scrapped it.

Just because you've succeeded with your startup doesn't mean that you know exactly what to do with the next one, which you were talking about earlier.

You have to crack the code, as you said.

And it's a process of trial and error and talking to a lot of people and figuring out what.

What do they.

What do they respond to and what do they need?

And what kind of problems can you solve that are so big for them that they're willing to pay you to do it?

Exactly.

Exactly.

All right, Sharon.

Fast fire Round Five questions in five words or less.

One word that describes your leadership style.

Empathetic.

Biggest myth about entrepreneurship you want to bust once and for all.

You don't need venture capital.

Exit Day one word to capture the feeling.

Disbelief.

If founders only focused on one thing in their first year, what would it be?

Customers.

Most underrated skill a founder can cultivate.

Oh, that's the hardest one.

Most underrated skill a founder can cultivate.

Is this a skill?

Resilience.

Resilience.

I agree with you.

It's hard being a founder.

It's harder than most things.

Right.

It's not for most people, but for those who are signed up for it and who have it as a calling, like you and me, it's just what we do.

So how can our listeners find you?

I know you have Sharon K. Gillenwater.com.

You have a substack called Scaling Soul.

Yep.

And you have a dealing with Joel.

And my main platform is TikTok.

And that's where I'm pretty unfiltered about entrepreneurship, managing a team and what's going on with me with this crazy new ride of figuring out if I'm going to build this company back.

I love it when you have a huge following on TikTok.

How did you do that?

You don't just mind my asking?

There were three entrepreneur to another right re inflection points and I'll tell you what I learned.

The first inflection point was I went on there and I shared all of my numbers for my exit.

I shared what we sold for, what I paid the lawyers, bankers and accountants, what we paid out to employees, how much I got, how much I paid in taxes and what I walked away with.

And that was my first real spike on TikTok.

The second big spike was this past July.

I went to a place in New York called Chautauqua and I had the craziest experience there, the rantiest TikTok about it.

And it is up to about 8.4 million views right now.

People are still watching it.

And it turned into a little series.

Has nothing to do with entrepreneurship and what I normally talk about, but what it taught me is people want the unfiltered me.

People like the unfiltered me.

I got some haters, but I got way more.

People are like, I love the way you tell stories.

So I realized I need to merge that Sharon that ranted on that TikTok and it was a nine minute video and people watched it all the way through.

I need to merge that style of delivery and storytelling with my entrepreneurial stuff.

So I've stopped scripting my videos.

I just talk.

And so that was the second inflection and then the third has been my story about Boardroom insiders being shut down and that's up to over 700,000 views and it's only been up for about a week.

And so yeah, I'm just, I'm still learning, I'm still learning how to do TikTok.

But people don't want shiny, polished, scripted.

They want unfiltered truth.

And I've also picked up quite a few editing hacks that I think make my videos more appealing.

The first is just really edit it down to the core of the story and speed up your audio just a little bit.

You speed it up a little bit.

Sometimes I speed it up to 1.3, sometimes that's a little fast.

But people say that they really like that.

They actually usually listen at a higher speed.

Speeding it up was appreciated.

It allows me to get more content in that 10 minute limit because both of those, and here's what I learned too is everyone's like, it has to be three minutes.

Surrender.

Those conventions and rules about TikTok are not altogether true.

What I've learned about social is if you chase what's working, the hooks or formats, by the time you do it, it's past.

So stop chasing and just do what's authentic to you.

Once I started doing that, it really took off.

The other thing is to engage with the people who comment.

Sometimes it's overwhelming.

On my Spencer Hotel and Spa video about the vacation, I think I'm up to over 10,000 comments, but I read every single one.

So there you have a real following, people listening who want to learn from you and that says something.

The path for you is reaching out to you and I am excited to have you back on the show and hear how things are in a year or two and watch as your story continues to unfold.

Thank you so much for being here today on the Wisdom of Women Show.

You have given us a lot to digest and such good stuff for all of the founders to all of our listeners.

Be sure to follow like and share the Wisdom of Women show on whatever your favorite listening platform and be sure to infuse more of your wisdom into your business.

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