September 11, 2025 • 31 mins
How do you build a tech company from scratch, scale it without venture capital, and sell it for $25 million? Sharon Gillenwater did exactly that—and today, she’s sharing the secrets, lessons, and mindset that made it happen. If you’re curious about entrepreneurship, bootstrapping, and making big impact, this is one conversation you can’t miss!💰 *Love The KAJ Masterclass? Now Profit With KAJ**Join The KAJ Inner Circle* → Premium, invitation-only access to my personal visibility strategies and insider guidance. https://www.linkedin.com/groups/14666045/*Explore The KAJ Hub* → Your complete gateway to connect, collaborate, feature, and access all KAJ Masterclass resources. https://www.thekajmasterclass.live/=================================👤 *EXPERT SPOTLIGHT*Sharon K. Gillenwater is a SaaS start-up adviser, Inc. 5000 entrepreneur, speaker and author. She is the co-founder of, respectively, Fidget.com and Boardroom Insiders—where she served as CEO. In 2022, Boardroom Insiders was acquired by Euromoney LLC, leading Gillenwater to a $25M exit. Gillenwater lives in the San Francisco Bay Area. Scaling with Soul is her first book.==================================🎙️ *ABOUT HOST KAJ*Khudania Ajay | 20+ years media experience (CNBC India, Reuters, PTI) | 2,000+ interviews conducted | Host of KAJ Masterclass LIVE — a top 1.5% globally ranked podcastWork with KAJ:📞 Book a Strategy Session — Media Training | Podcast Launch | Business Storytelling💼 Partnerships & Collaborations — kajmasterclass@gmail.com🎙️ Be a Guest — Get featured on a top ranked podcast📈 Speaking & Consulting — Build authority and monetize your expertiseConnect with KAJ:▶️ LinkedIn: https://www.linkedin.com/in/ajaykhudania/🌐 Website: https://www.thekajmasterclass.live/=================================📺 *EPISODE CHAPTERS*00:00 Startup Journey03:25 Venture Capital Warning06:26 Scaling Boardroom Insiders10:12 AI Perspective14:58 Demystifying Entrepreneurship18:34 Overcoming Challenges20:46 Scaling With Soul24:01 Company Culture28:20 Entrepreneur Insights================================🎁 *EXCLUSIVE OFFERS*👗 Ethnics Land: 20% OFF Premium Indian Handloom Sarees — Use code KAJ20 👉 https://www.ethnicsland.com🎙️ Be My Guest: FREE consultation when you join 👉 https://www.podmatch.com/hostdetailpreview/kaj=================================📱 *The KAJ ECOSYSTEM*▶️ Main Channel: https://www.youtube.com/@kajmasterclass📚 Author Focus: https://www.youtube.com/@kajmasterclassAuthors🎧 Audio Podcast: https://pod.link/thekajstudio📖 Blog & Resources: https://www.thekajmasterclass.live/blog===================================💬 *ENGAGE NOW*👍 LIKE if this added value🔔 SUBSCRIBE for daily success strategies💭 COMMENT: What’s your biggest takeaway?📤 SHARE with someone ready to level up❤️ SUPPORT KAJ MASTERCLASS:☕ https://ko-fi.com/kajmasterclass💸 https://www.paypal.com/paypalme/kajmasterclass======================================🎵 Audio Credit: "Misfits (Instrumental)" by RYYZNConversations that matter — connecting ideas, people, and stories.#kajexperts #kajmasterclass #khudaniaajay
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:24):
Welcome to this very special edition of The Cage a
masterclass live, the show which ensures that you profit from
your time spent here with experts, either through the industry insights,
information or simply learning from them. And today we have
Sharon gillen Waters. He's a tech startup founder and business
(00:45):
executive whose mission is to demystify entrepreneurship and make it
more accessible fit work for everyone. In twenty twenty twos,
Sharon showed Boardroom Insiders a business a build and skilled
with no venture fun and she showed it for twenty
five million dollars.
Speaker 2 (01:03):
Welcome to the show.
Speaker 3 (01:05):
Sharon, thank you so much for having me.
Speaker 1 (01:09):
You're welcome, Welcome to the show. Welcome to India in
this online form, Sharon, and I'm sure not just in India,
but a lot of people will benefit from what you are,
what you have done, what you are doing, and what
we'll be discussing right now. We'll be talking about how
one can build and sell a tech company with your experience.
(01:32):
So first to understand Sharon, you know, tell us a
bit about your journey.
Speaker 2 (01:36):
And in that.
Speaker 1 (01:37):
Journey when you talk about no venture funding, why no
venture funding?
Speaker 2 (01:42):
What the enemy with those guys.
Speaker 3 (01:44):
Well, part of the reality of my journey is I
did start another company back in two thousand, actually nineteen
ninety nine, way back in ninety nine, and at the
beginning of the dot com crash, which started in the
spring of twenty twenty, we were able to raise three
million in venture funding, but it killed the company. That's
(02:06):
a very long story which I tell on TikTok. But
when it came time to start my second startup in
two thousand and eight, I was very opposed to raising
venture capital for that reason because of the experience that
I had had. So what I ended up doing is
I did have some angel funding from an angel who
(02:29):
had sold his company the previous year for a lot
of money, and so I raised a total of about
two hundred thousand and gave away about thirteen percent of
the company to various shareholders for that amount, and we
sold for twenty five million in cash. So we did
pretty well, and I did pretty well personally, being able
(02:50):
to hold onto about fifty seven percent of the company.
Speaker 1 (02:55):
Absolutely absolutely, So from this venture capital part itself, what
is it that one should uh, you know, avoid taking?
Speaker 2 (03:07):
Why did you kill your company? I want to understand.
Speaker 1 (03:09):
Nowadays The thing is that people start a company to
sell it, and so that.
Speaker 2 (03:14):
Is first the angel investors.
Speaker 1 (03:16):
Then these sort of investors raise the value valuation, talk
about being a unicorn, and then so and the vcs
play a big role.
Speaker 2 (03:25):
So that could have helped. So why why do you
why how did they kill the company?
Speaker 1 (03:29):
Means in a in a way wherever you can share,
not too much of details if you don't want to,
but the learning part of it. How do they operate?
Which you do do not like like as a founder
or co founder.
Speaker 3 (03:43):
Well, there's different types of venture capital and in my
case in that company that I started in ninety nine,
we raised three three million, but they were an incubator
as well. And what that means is they take a
majority stake in the company, so I think they had
like FI fifty one or fifty five percent for something
like that. And they take a majority of seats on
(04:05):
your board, so they do have control and they offer services.
You turn over all of your HR, your finance, you're legal,
your accounting to them. They have all of those resources
in house. And as an entrepreneur who's been bootstrapping, it
sounds very attractive because I was doing all the accounting
and the know all of that, and I really don't
(04:26):
have the skills or expertise.
Speaker 2 (04:27):
To do it.
Speaker 3 (04:28):
So I was excited to turn all of that over
to them. But when they turned on us because of
the dot com crash and they decided they wanted to
renege on our funding, it made it that much easier
for them to do so because one of the things
they did that we found out about later is they
never put that three million in our dedicated bank account.
(04:48):
They only put one million in, so we were missing out,
for example, on all the interest that would have been accruing,
and so they never really fully funded us, which we
didn't know about at the time. But we start sarted
scaling up because when you raise venture capital that in
those days, that's what is expected, is you start to
spend it. You get a bigger office, you hire people,
(05:11):
you sign long term agreements for things like, you know,
having your website hosted on in a server farm. And
so we incurred a lot of expenses that I then
had to unwind when they renegged on the funding, and
they actually tried to sue us for fraud. So it
was just a huge mess. And what I realized after
(05:33):
the fact is that I took that money because I
was tired, because being an entrepreneur and wearing so many
hats and doing everything, including things that you really don't
know how to do, is exhausting. And I realized that
if I had just kept bootstrapping that company, I could
have kept it going throughout a prolonged crash because the
(05:55):
costs originally were quite low and we were bringing in
ad revenue. So that was my lesson learned and why
the second time around I decided to avoid all.
Speaker 1 (06:06):
Of that.
Speaker 2 (06:08):
Absolutely. So how did you scale up you know, Boardroom Insiders?
Speaker 1 (06:12):
What did what? What does this company do? And and
it was acquired by uh, you know, no less than
euro euro money, So that's that's it.
Speaker 2 (06:21):
That's it.
Speaker 1 (06:22):
So tell us a bit about the company and how
did you scale it up and and and so that
you know, a lot of people can have that sort
of a learning from your story.
Speaker 3 (06:32):
Yeah, well it was. It's called Boardroom Insiders, and the
brand still exists and it's in what euro Money calls
the people Intelligence business. So I was doing consulting in
tech marketing with all the biggie's in Silicon Valley, Cisco, VMware, Dell, EMC, Oracle,
(06:54):
and they all had the same challenge, which was they
were starting to have to sell their deals into the
C suite because the deals were getting so huge, and
also technology was starting to affect every single part of
the organization, so c suite they wanted to know what
these deals were about and what the business value was
(07:14):
that was being delivered. So the conversation is very different
when you're talking to the CFO versus like a VP
of infrastructure. You're not talking about products, You're talking about
business impact. And so I created a database of Fortune
five hundred executives that gave insight into their business initiatives,
their backgrounds, their hobbies so that sales and marketers could
(07:38):
have a hook to get their foot in the door
and have conversations with those key influencers and decision makers.
So I started out with the database of profiles, and
later I built a software over the top of it
that would allow you to create groups of executives, real
executives and discover what they all have in common and
(08:00):
what they care about most commonly. And that was important
for people like event marketers who were planning high level
chief information officer events. It helped them figure out what
their content strategy should be their audience acquisition strategy and
how to engage between their executives and the customer executives.
(08:22):
So the content that we produced was quite labor intensive.
It was done mainly by human beings. There was very
little data scraping. We had a large team in South
India that helped support that through a vendor and using
things like the outsourced team or fractional CFO or having
(08:44):
a stable of contractors when we to handle production spikes.
Those were some of our secrets that we used for
bootstrapping while still scaling the business, because when you're bootstrapping,
you're trying to be as capital efficient as possible. You're
trying to spend as little money as possible on essential
(09:07):
resources like the fractional CFO. For example, we didn't need
a full time CFO, but we certainly needed one to
help us forecast our growth based on our existing sales
pipeline and also give us permission to spend. He gave
us permission to pull the trigger on key investments, and
(09:29):
if we didn't have that, we were not sure whether
we could sustain those new expenses long term. And that
also helped us get our financials ready for due diligence,
So that was critical.
Speaker 2 (09:44):
Absolutely. And what is prigio dot com?
Speaker 1 (09:47):
Is it the same model as euro money or something different?
Speaker 3 (09:52):
Ohfidget dot com was my first startup that imploded when
we had the dispute over the VC funding.
Speaker 1 (10:00):
Right right now, Sharon, if you were to you sold
this boardroom insider, if I understand in twenty twenty two,
and immediately after that, a.
Speaker 2 (10:10):
Few months later on this whole artificial intelligence thing came
in in it in full force and it's now you know,
opening up.
Speaker 1 (10:19):
So if you were to look into the tech sector
today and look at you know, creating something, would you
look at it from an artificial intelligence sort of an
outlook that this is the area I would look at?
Speaker 2 (10:32):
Or are there other opportunity? Why I asked this that
a lot of people are so focused just.
Speaker 1 (10:38):
On AI itself, and AI also dependent on several just
a few companies like chad Gpity or or Perplexity or
any of the things.
Speaker 2 (10:50):
Cloud can take any name, and they're built around that.
Speaker 1 (10:55):
I see, as a person who does not understand too
much of these things, it's too much risk on other
companies rather than your own strength.
Speaker 2 (11:04):
How do you see this would you.
Speaker 1 (11:07):
Think differently when you are creating something or is it
like okay, create something, sell past and move out and
make your money.
Speaker 2 (11:15):
How do you look at it?
Speaker 1 (11:16):
What is your advice to youngsters who especially would want
to get into entrepreneurship on this line?
Speaker 3 (11:23):
Well, that's those are big questions, and I think what
you ask two main questions, you know what, how do
I view AI? And then how to build a business,
a viable business that you can then sell? And I
see a common thread there, and that's hype. You know,
(11:44):
AI is indisputably a huge game changer, and like a
technology that is the equivalent of you know, the game changer.
I think the last one was mobile, And but it's
a tool. I don't think it's a thing in and
of itself unless you're actually developing and refining you know,
(12:08):
the AI and the language models. But it's a tool
to do other things. So, for example, if I were
still running Boardroom Insiders, I would be leveraging AI as
a tool to make the editorial team more productive. But
the editorial team wouldn't go away. I've used AI tools
(12:30):
enough to know that they do not produce content that
is customer ready, as we would say, you know, in
our market, we were delivering content on Fortune five hundred
executives that sales and marketing teams were going to use
to engage those people. So it had to be one
(12:51):
hundred percent accurate, and it had to be one hundred
percent current, and you cannot rely on AI to deliver
that right now with out some human intervention and human verification.
So if I were running boardroom Insiders, I would be
looking at how we can leverage AI for that first
(13:13):
pass of our content and then have our editors check
it and verify it. So we would be using it
to be more productive, but not to replace human beings.
And I believe that that's going to be critical, at
least in the next few years as these models get refined.
On the side of you know, building a company, there's
(13:34):
lots of hype and building of businesses to scale them
quickly and sell them and get your money and get out,
regardless of whether that's going to be a good product
or a good business for the long term. I always
recommend building a product that customers love, providing excellent customer service,
and that's how you build a sustainable business, and I
(13:57):
think it takes the risk out of it for entrepreneur
to focus that way, because if for some reason they're
not able to sell it, at least they've got a
great lifestyle business. You can create a great what we
call lifestyle business which gets to the point where it's
generating lots of cash, so you can pay yourself well,
(14:17):
you can pay your employees well, you can build a
great team that, you can build a great place to work,
a company that customers love. And that's all a very
good thing. And you can still get a lot of
value out of that even if you don't sell it.
But all of those things will also help you get
to a point where you are a viable to acquisition target.
Speaker 1 (14:39):
Absolutely absolutely well put shadow. Now, let's talk about entrepreneurship.
Your mission is to demystify entrepreneurship and make it more
accessible to all.
Speaker 2 (14:51):
Do you think it's not.
Speaker 1 (14:52):
Accessible to all? What is the hurdle that people think?
Is it mental block? What is it that you actually
want to de mystify in entrepreneurs.
Speaker 3 (15:04):
It's there are so many hurdles. Yes, one of them
could be mindset. And that's why I put that word
demystify in there, because especially if you're in the in
Silicon Valley area, and maybe it's the same in certain
parts of India. We hear all these stories about the
(15:26):
unicorn entrepreneurs and the entrepreneurs that have, you know, high
profile exits and for hundreds of millions of dollars, and
the average person, even if they think they might have
a great idea, they can't picture themselves operating in that
at that level or succeeding at that level because of
perhaps mindset issues or perhaps access to networks like the
(15:50):
Ivy League to Silicon Valley pipeline, where you have access
to all these who could fund your company with just
a phone call, right. I didn't have that. I grew
up in a working class family with parents who didn't
go to college. I didn't discover business until age thirty.
I didn't work at my startup until age thirty and
(16:12):
then I got really into it. But before that I
had no idea, so I've been having to learn as
I go along. I did not get you know, I
did not go to school and learn about entrepreneurship, finance,
or technology. So I was a little bit of a
fish out of water. And for that reason, I came
across a lot of naysayers or people who dismissed me
(16:34):
because I didn't have the right connections or the right capital.
And I think it it makes it so people quit
before they even get started, even if they have a
great idea, because there's a whole group of people out
there who work in a field and they start to
(16:55):
see a problem. The same problem comes up over and
over again, and they might have an idea for how
to fix that, and maybe that idea is, you know,
a simple app, or maybe you can build a whole
company around it like I did. And I know those
people are out there because I've met them and they
don't come from that Ivy League pipeline. They've come from
(17:17):
working in the trenches in a space where they want
to solve a problem. And those are viable entrepreneurs. That's
how I started and I had a very good exit,
and I want to encourage people like me who are
in that same situation to go for it and you know,
build their company. And there are ways you could do
(17:39):
it as a bootstrapper because the barriers to entry have
never been lower. It's there are low code, no code
tools you can use to build your app. There are
really easy to use tools that you can build to
use to build your first website, and there are hundreds,
if not thousands of tools out there that you can
(18:00):
use to run your whole business digitally. And so that's
what I mean when I say, you know, the barriers
to entry have never been lower, and we are really
in a golden age for bootstrapping and entrepreneurship.
Speaker 1 (18:15):
Absolutely, So some of the challenges that you paced during
your building up the company that Boatroom insiders today, do
you think those challenges have gone away with the with
the coming of artificial intelligence or more technology, or those
challenges still remain. What are some of the challenges that
(18:36):
still remain and which you want other, you know, budding
entrepreneurs to be aware of.
Speaker 3 (18:44):
I think all the challenges still remain. Our challenges were
not so much around technology or issues that AI might solve.
AI might alleviate some things and make the company more productive,
allow us to do more with less, But I think
(19:06):
the challenges remain the same, and some of those are financing.
How can you sustain yourself while you get to profitability
and get to the point of profitability where you have
enough to pay yourself. So that's one issue and how
I dealt with that as I stayed. I kept consulting
for six years. The first six years of Boardroom Insiders,
(19:27):
I had one foot in Boardroom Insiders and one foot
in the consulting world because that was very well paid work,
and it also was working directly with the customers I
was targeting with Boardroom Insiders, so it allowed me to
really understand all of their issues. I sat in meetings
with them every single day, so I understood what they
(19:47):
wanted and what they were dealing with. A second big
challenge for us for years was getting our offer right.
What are we delivering, how are we delivering it, and
what are we charging our customers. That is surprisingly difficult
to get right, and I've heard this from other entrepreneurs
(20:07):
as well. So that's something we struggled with for quite
a few years. And I thought I had one more
in mind, you know, when it did come to technology,
Mike founder and I were both non technical founders, and
so one of the biggest challenges we had was finding
(20:28):
the right development partner, and we struggled with that, but
eventually we did find the right partner, and once we
did that, there was really no stopping us.
Speaker 1 (20:40):
Right right, Sharon, Now, let's come to learn a bit
more from your books. Scaling with Soul. It's a nice name.
How how did you get down to this name? And
where did this soul coming into the picture?
Speaker 3 (20:55):
Well, we did use AI as a first pass for
coming up with titles, so that's one way that AI helped,
and I think they I think the AI brought up
scale and soul and we ended up putting them together.
But Scaling with Soul really refers to building and selling
(21:17):
a company, having a life changing exit without losing your
humanity when it comes to how you treat your customers
and your team. We built a phenomenal team, a happy,
productive team, and still had great business outcomes. And I
(21:39):
think that the whole title. And you know there's a
curse word in the sub head which you didn't mention,
and I won't mention here. But I'm in the Bay Area,
in the San Francisco Bay Area, in the center of
the entrepreneurial universe, at least in the United States, and
there's a lot of really bad behavior here. There's a
(22:02):
stereotype of the tech bro and people in the city
who are not in tech, they don't have a good reputation,
and there's a lot of bad behavior online by very
high profile entrepreneurs. And the latest example of that is
there was some proposed legislation in California called the Right
(22:23):
to Disconnect and it had to do with employees having
the right to unplug after five PM and on the weekends,
and some of the tech leaders here just went crazy
over that, and they were very hyperbolic about it. They're
going to legislate us into poverty, They're going to ruin innovation,
(22:44):
and blah blah blah. You know, you don't have to
put unreasonable demands on your employees to build a healthy,
profitable company. Our employees knew they were expected to unplug
after or five expected to take their time off, their vacations,
their weekends, their holidays, and we still were incredibly successful.
(23:09):
So I don't think it's one or the other. My
story proves that. And by the way, you don't want
to burn out your employees and lose them. We had
over a ninety percent retention rate. So I'm trying to
convey to entrepreneurs that they don't have to be jerks
or be adversaries to their own team to be successful financially.
(23:31):
It's just not an either or situation.
Speaker 1 (23:36):
Absolutely, Sharon, absolutely you said it right, And this thing,
this sort of empathy or understanding your employees better worklife
balance is so much needed in today's time, especially in
the backdrop of the great resignation and quite witting and
if they are not understanding, I don't know what sort
(23:56):
of a example it will set because it will create
hurdles rather than creating. Already the world is talking about
four de week, then that will be much more. Perhaps
those discussions happening. But in terms of you see a
lot of UH founders nowadays, especially in tech, they create
this company for you know, with the intention of selling it,
(24:19):
you know, so that there's nothing wrong with that with
a good, good exit. But as a founder, when you
are building a company and going for customer service, customer
value for the customer, and then there is a company
which comes in and takes your company and wants to
close it because it is competing with what they are doing,
(24:41):
and several of these these things as almost become a
non for for especially the big companies. How do you
see it? It means you have dealt You talked about
customer service. Initially you talk about the customer UH, and
there is UH and and then suddenly all that customer
is gone, uh for for the money, and then the
(25:02):
whole ecosystem is gone back to the same thing. The
big company does not worry about your customers, and.
Speaker 2 (25:09):
It is God.
Speaker 1 (25:09):
How do you see this sort of a culture almost
developing in especially in the tech tech industry. It is
happening also in the parma sector, but with a lot
of acquisitions happening in that and then the prices increases.
And I talk it because I see it more from
a India perspective, where people have limited amount of money
(25:33):
to pay for any particular product.
Speaker 2 (25:35):
But it gives.
Speaker 1 (25:37):
Undew advantage to some companies, make them so big that
they can rule over people's life. So how do you
see this part in tech? How do you look at
it from someone who talks about the customers?
Speaker 3 (25:51):
Well, that's a big question. And companies that are doing that,
they're just in a much different league than mine was.
That's you know. One thing that I heard recently is
that I don't remember the exact figure, but the amount
of venture capital that ends up with Meta, Google, Amazon
(26:16):
is astonishing. I think it was something like thirty to
forty percent of all venture capital just goes straight to
those companies because you have. The startups are all advertising, right,
and that is a problem. That is a big problem.
I feel like that's stifling growth in innovation itself. But
(26:38):
that's those companies are enormous and I would never claim
to know or play in those spaces, right. But with
my company that I built, when it came time to sell,
it was very important to me that the technology that
we that we built and the tool that we've bill
(27:00):
live on not only to continue to serve our customers,
but to have a place for our team to land
that would be a good place for them. And so
we had lots of conversations about that. If a company
had come to us and offered to buy us but
(27:22):
said we're going to just shut it down after that,
I don't know if we would have done that. I mean,
we clearly, my founder and I needed to exit for
our you know, financial freedom and future. We needed to
exit eventually, but we probably would have held out for
a different kind of opportunity because it was very important
(27:45):
to us to keep serving our customers and our team.
And fortunately, you know, euro money, it's now no longer
euro money. They've spun it off and the whole company
is called ultrata, But I'm hearing great things from both
our customers and our team in terms of what that
experience has been like for them. So that makes me happy.
Speaker 2 (28:10):
Absolutely.
Speaker 1 (28:10):
So when you talk about demastifying entrepreneurship, how do you
want the new age entrepreneur to look at this whole
entrepreneurship business as is it only about money or is
it about you know, some bigger motivation for some bigger purpose.
How do you how would you like to help them
(28:31):
understand how their entrepreneurship journey can be or should be.
Speaker 3 (28:38):
Yeah, it's about money and financial freedom, of course, but
it's also about the experience and what they can learn
and do along the way, and how surprising and rewarding
it other aspects of the journey can be apart from
(28:58):
making the money, you know, for me, one of the
unexpected joys of running the company was building the team
and watching especially young people just right out of college
or a couple of years out of college, find their
footing and start to contribute and start to grow into leaders.
(29:18):
That was wonderful for me to experience, and it's also
a great journey in terms of developing your own self
confidence and your own leadership skills, and just the knowledge
starts to become second hand. You don't have to think
(29:41):
so hard when it's time to make a decision. You
start to know what the right decision is based on
the way that you've been operating the company, what your
culture looks like that you've developed, and your own learnings.
You know, I made a lot of mistakes along the way,
but I learned from those mistakes and then I would
(30:02):
incorporate that into my leadership style moving forward.
Speaker 1 (30:08):
Absolutely, there is so much to learn from you, Sharton,
and a lot of people would like to connect with you,
want to learn from you, you know, want to read
your book. So what is the best way for them
to connect with you?
Speaker 3 (30:22):
Well, I have various ways. I do have a website
Sharon Ka middle initial kgillanwater dot com, and from there
they can find all my social media and my blog
and my newsletter and book announcements. The platform that I
use the most where I post not only everything I
post everywhere else, but I also get a little bit
(30:45):
more personal on is TikTok and my handle there is
Sharon Ka Gillan Water with two l's. And you have
to be careful because unfortunately I have a lot of
impersonators on TikTok so just look for the version of
me that has over twenty one thousand followers, and that's me.
Speaker 2 (31:07):
Wonderful, wonderful.
Speaker 1 (31:08):
With this, it's a wrap on this very special edition
of the KG Masterclass Life.
Speaker 2 (31:13):
Thank you so much, indeed for joining us.
Speaker 3 (31:16):
Thank you,
Welcome to this very special edition of The Cage a
masterclass live, the show which ensures that you profit from
your time spent here with experts, either through the industry insights,
information or simply learning from them. And today we have
Sharon gillen Waters. He's a tech startup founder and business
(00:45):
executive whose mission is to demystify entrepreneurship and make it
more accessible fit work for everyone. In twenty twenty twos,
Sharon showed Boardroom Insiders a business a build and skilled
with no venture fun and she showed it for twenty
five million dollars.
Speaker 2 (01:03):
Welcome to the show.
Speaker 3 (01:05):
Sharon, thank you so much for having me.
Speaker 1 (01:09):
You're welcome, Welcome to the show. Welcome to India in
this online form, Sharon, and I'm sure not just in India,
but a lot of people will benefit from what you are,
what you have done, what you are doing, and what
we'll be discussing right now. We'll be talking about how
one can build and sell a tech company with your experience.
(01:32):
So first to understand Sharon, you know, tell us a
bit about your journey.
Speaker 2 (01:36):
And in that.
Speaker 1 (01:37):
Journey when you talk about no venture funding, why no
venture funding?
Speaker 2 (01:42):
What the enemy with those guys.
Speaker 3 (01:44):
Well, part of the reality of my journey is I
did start another company back in two thousand, actually nineteen
ninety nine, way back in ninety nine, and at the
beginning of the dot com crash, which started in the
spring of twenty twenty, we were able to raise three
million in venture funding, but it killed the company. That's
(02:06):
a very long story which I tell on TikTok. But
when it came time to start my second startup in
two thousand and eight, I was very opposed to raising
venture capital for that reason because of the experience that
I had had. So what I ended up doing is
I did have some angel funding from an angel who
(02:29):
had sold his company the previous year for a lot
of money, and so I raised a total of about
two hundred thousand and gave away about thirteen percent of
the company to various shareholders for that amount, and we
sold for twenty five million in cash. So we did
pretty well, and I did pretty well personally, being able
(02:50):
to hold onto about fifty seven percent of the company.
Speaker 1 (02:55):
Absolutely absolutely, So from this venture capital part itself, what
is it that one should uh, you know, avoid taking?
Speaker 2 (03:07):
Why did you kill your company? I want to understand.
Speaker 1 (03:09):
Nowadays The thing is that people start a company to
sell it, and so that.
Speaker 2 (03:14):
Is first the angel investors.
Speaker 1 (03:16):
Then these sort of investors raise the value valuation, talk
about being a unicorn, and then so and the vcs
play a big role.
Speaker 2 (03:25):
So that could have helped. So why why do you
why how did they kill the company?
Speaker 1 (03:29):
Means in a in a way wherever you can share,
not too much of details if you don't want to,
but the learning part of it. How do they operate?
Which you do do not like like as a founder
or co founder.
Speaker 3 (03:43):
Well, there's different types of venture capital and in my
case in that company that I started in ninety nine,
we raised three three million, but they were an incubator
as well. And what that means is they take a
majority stake in the company, so I think they had
like FI fifty one or fifty five percent for something
like that. And they take a majority of seats on
(04:05):
your board, so they do have control and they offer services.
You turn over all of your HR, your finance, you're legal,
your accounting to them. They have all of those resources
in house. And as an entrepreneur who's been bootstrapping, it
sounds very attractive because I was doing all the accounting
and the know all of that, and I really don't
(04:26):
have the skills or expertise.
Speaker 2 (04:27):
To do it.
Speaker 3 (04:28):
So I was excited to turn all of that over
to them. But when they turned on us because of
the dot com crash and they decided they wanted to
renege on our funding, it made it that much easier
for them to do so because one of the things
they did that we found out about later is they
never put that three million in our dedicated bank account.
(04:48):
They only put one million in, so we were missing out,
for example, on all the interest that would have been accruing,
and so they never really fully funded us, which we
didn't know about at the time. But we start sarted
scaling up because when you raise venture capital that in
those days, that's what is expected, is you start to
spend it. You get a bigger office, you hire people,
(05:11):
you sign long term agreements for things like, you know,
having your website hosted on in a server farm. And
so we incurred a lot of expenses that I then
had to unwind when they renegged on the funding, and
they actually tried to sue us for fraud. So it
was just a huge mess. And what I realized after
(05:33):
the fact is that I took that money because I
was tired, because being an entrepreneur and wearing so many
hats and doing everything, including things that you really don't
know how to do, is exhausting. And I realized that
if I had just kept bootstrapping that company, I could
have kept it going throughout a prolonged crash because the
(05:55):
costs originally were quite low and we were bringing in
ad revenue. So that was my lesson learned and why
the second time around I decided to avoid all.
Speaker 1 (06:06):
Of that.
Speaker 2 (06:08):
Absolutely. So how did you scale up you know, Boardroom Insiders?
Speaker 1 (06:12):
What did what? What does this company do? And and
it was acquired by uh, you know, no less than
euro euro money, So that's that's it.
Speaker 2 (06:21):
That's it.
Speaker 1 (06:22):
So tell us a bit about the company and how
did you scale it up and and and so that
you know, a lot of people can have that sort
of a learning from your story.
Speaker 3 (06:32):
Yeah, well it was. It's called Boardroom Insiders, and the
brand still exists and it's in what euro Money calls
the people Intelligence business. So I was doing consulting in
tech marketing with all the biggie's in Silicon Valley, Cisco, VMware, Dell, EMC, Oracle,
(06:54):
and they all had the same challenge, which was they
were starting to have to sell their deals into the
C suite because the deals were getting so huge, and
also technology was starting to affect every single part of
the organization, so c suite they wanted to know what
these deals were about and what the business value was
(07:14):
that was being delivered. So the conversation is very different
when you're talking to the CFO versus like a VP
of infrastructure. You're not talking about products, You're talking about
business impact. And so I created a database of Fortune
five hundred executives that gave insight into their business initiatives,
their backgrounds, their hobbies so that sales and marketers could
(07:38):
have a hook to get their foot in the door
and have conversations with those key influencers and decision makers.
So I started out with the database of profiles, and
later I built a software over the top of it
that would allow you to create groups of executives, real
executives and discover what they all have in common and
(08:00):
what they care about most commonly. And that was important
for people like event marketers who were planning high level
chief information officer events. It helped them figure out what
their content strategy should be their audience acquisition strategy and
how to engage between their executives and the customer executives.
(08:22):
So the content that we produced was quite labor intensive.
It was done mainly by human beings. There was very
little data scraping. We had a large team in South
India that helped support that through a vendor and using
things like the outsourced team or fractional CFO or having
(08:44):
a stable of contractors when we to handle production spikes.
Those were some of our secrets that we used for
bootstrapping while still scaling the business, because when you're bootstrapping,
you're trying to be as capital efficient as possible. You're
trying to spend as little money as possible on essential
(09:07):
resources like the fractional CFO. For example, we didn't need
a full time CFO, but we certainly needed one to
help us forecast our growth based on our existing sales
pipeline and also give us permission to spend. He gave
us permission to pull the trigger on key investments, and
(09:29):
if we didn't have that, we were not sure whether
we could sustain those new expenses long term. And that
also helped us get our financials ready for due diligence,
So that was critical.
Speaker 2 (09:44):
Absolutely. And what is prigio dot com?
Speaker 1 (09:47):
Is it the same model as euro money or something different?
Speaker 3 (09:52):
Ohfidget dot com was my first startup that imploded when
we had the dispute over the VC funding.
Speaker 1 (10:00):
Right right now, Sharon, if you were to you sold
this boardroom insider, if I understand in twenty twenty two,
and immediately after that, a.
Speaker 2 (10:10):
Few months later on this whole artificial intelligence thing came
in in it in full force and it's now you know,
opening up.
Speaker 1 (10:19):
So if you were to look into the tech sector
today and look at you know, creating something, would you
look at it from an artificial intelligence sort of an
outlook that this is the area I would look at?
Speaker 2 (10:32):
Or are there other opportunity? Why I asked this that
a lot of people are so focused just.
Speaker 1 (10:38):
On AI itself, and AI also dependent on several just
a few companies like chad Gpity or or Perplexity or
any of the things.
Speaker 2 (10:50):
Cloud can take any name, and they're built around that.
Speaker 1 (10:55):
I see, as a person who does not understand too
much of these things, it's too much risk on other
companies rather than your own strength.
Speaker 2 (11:04):
How do you see this would you.
Speaker 1 (11:07):
Think differently when you are creating something or is it
like okay, create something, sell past and move out and
make your money.
Speaker 2 (11:15):
How do you look at it?
Speaker 1 (11:16):
What is your advice to youngsters who especially would want
to get into entrepreneurship on this line?
Speaker 3 (11:23):
Well, that's those are big questions, and I think what
you ask two main questions, you know what, how do
I view AI? And then how to build a business,
a viable business that you can then sell? And I
see a common thread there, and that's hype. You know,
(11:44):
AI is indisputably a huge game changer, and like a
technology that is the equivalent of you know, the game changer.
I think the last one was mobile, And but it's
a tool. I don't think it's a thing in and
of itself unless you're actually developing and refining you know,
(12:08):
the AI and the language models. But it's a tool
to do other things. So, for example, if I were
still running Boardroom Insiders, I would be leveraging AI as
a tool to make the editorial team more productive. But
the editorial team wouldn't go away. I've used AI tools
(12:30):
enough to know that they do not produce content that
is customer ready, as we would say, you know, in
our market, we were delivering content on Fortune five hundred
executives that sales and marketing teams were going to use
to engage those people. So it had to be one
(12:51):
hundred percent accurate, and it had to be one hundred
percent current, and you cannot rely on AI to deliver
that right now with out some human intervention and human verification.
So if I were running boardroom Insiders, I would be
looking at how we can leverage AI for that first
(13:13):
pass of our content and then have our editors check
it and verify it. So we would be using it
to be more productive, but not to replace human beings.
And I believe that that's going to be critical, at
least in the next few years as these models get refined.
On the side of you know, building a company, there's
(13:34):
lots of hype and building of businesses to scale them
quickly and sell them and get your money and get out,
regardless of whether that's going to be a good product
or a good business for the long term. I always
recommend building a product that customers love, providing excellent customer service,
and that's how you build a sustainable business, and I
(13:57):
think it takes the risk out of it for entrepreneur
to focus that way, because if for some reason they're
not able to sell it, at least they've got a
great lifestyle business. You can create a great what we
call lifestyle business which gets to the point where it's
generating lots of cash, so you can pay yourself well,
(14:17):
you can pay your employees well, you can build a
great team that, you can build a great place to work,
a company that customers love. And that's all a very
good thing. And you can still get a lot of
value out of that even if you don't sell it.
But all of those things will also help you get
to a point where you are a viable to acquisition target.
Speaker 1 (14:39):
Absolutely absolutely well put shadow. Now, let's talk about entrepreneurship.
Your mission is to demystify entrepreneurship and make it more
accessible to all.
Speaker 2 (14:51):
Do you think it's not.
Speaker 1 (14:52):
Accessible to all? What is the hurdle that people think?
Is it mental block? What is it that you actually
want to de mystify in entrepreneurs.
Speaker 3 (15:04):
It's there are so many hurdles. Yes, one of them
could be mindset. And that's why I put that word
demystify in there, because especially if you're in the in
Silicon Valley area, and maybe it's the same in certain
parts of India. We hear all these stories about the
(15:26):
unicorn entrepreneurs and the entrepreneurs that have, you know, high
profile exits and for hundreds of millions of dollars, and
the average person, even if they think they might have
a great idea, they can't picture themselves operating in that
at that level or succeeding at that level because of
perhaps mindset issues or perhaps access to networks like the
(15:50):
Ivy League to Silicon Valley pipeline, where you have access
to all these who could fund your company with just
a phone call, right. I didn't have that. I grew
up in a working class family with parents who didn't
go to college. I didn't discover business until age thirty.
I didn't work at my startup until age thirty and
(16:12):
then I got really into it. But before that I
had no idea, so I've been having to learn as
I go along. I did not get you know, I
did not go to school and learn about entrepreneurship, finance,
or technology. So I was a little bit of a
fish out of water. And for that reason, I came
across a lot of naysayers or people who dismissed me
(16:34):
because I didn't have the right connections or the right capital.
And I think it it makes it so people quit
before they even get started, even if they have a
great idea, because there's a whole group of people out
there who work in a field and they start to
(16:55):
see a problem. The same problem comes up over and
over again, and they might have an idea for how
to fix that, and maybe that idea is, you know,
a simple app, or maybe you can build a whole
company around it like I did. And I know those
people are out there because I've met them and they
don't come from that Ivy League pipeline. They've come from
(17:17):
working in the trenches in a space where they want
to solve a problem. And those are viable entrepreneurs. That's
how I started and I had a very good exit,
and I want to encourage people like me who are
in that same situation to go for it and you know,
build their company. And there are ways you could do
(17:39):
it as a bootstrapper because the barriers to entry have
never been lower. It's there are low code, no code
tools you can use to build your app. There are
really easy to use tools that you can build to
use to build your first website, and there are hundreds,
if not thousands of tools out there that you can
(18:00):
use to run your whole business digitally. And so that's
what I mean when I say, you know, the barriers
to entry have never been lower, and we are really
in a golden age for bootstrapping and entrepreneurship.
Speaker 1 (18:15):
Absolutely, So some of the challenges that you paced during
your building up the company that Boatroom insiders today, do
you think those challenges have gone away with the with
the coming of artificial intelligence or more technology, or those
challenges still remain. What are some of the challenges that
(18:36):
still remain and which you want other, you know, budding
entrepreneurs to be aware of.
Speaker 3 (18:44):
I think all the challenges still remain. Our challenges were
not so much around technology or issues that AI might solve.
AI might alleviate some things and make the company more productive,
allow us to do more with less, But I think
(19:06):
the challenges remain the same, and some of those are financing.
How can you sustain yourself while you get to profitability
and get to the point of profitability where you have
enough to pay yourself. So that's one issue and how
I dealt with that as I stayed. I kept consulting
for six years. The first six years of Boardroom Insiders,
(19:27):
I had one foot in Boardroom Insiders and one foot
in the consulting world because that was very well paid work,
and it also was working directly with the customers I
was targeting with Boardroom Insiders, so it allowed me to
really understand all of their issues. I sat in meetings
with them every single day, so I understood what they
(19:47):
wanted and what they were dealing with. A second big
challenge for us for years was getting our offer right.
What are we delivering, how are we delivering it, and
what are we charging our customers. That is surprisingly difficult
to get right, and I've heard this from other entrepreneurs
(20:07):
as well. So that's something we struggled with for quite
a few years. And I thought I had one more
in mind, you know, when it did come to technology,
Mike founder and I were both non technical founders, and
so one of the biggest challenges we had was finding
(20:28):
the right development partner, and we struggled with that, but
eventually we did find the right partner, and once we
did that, there was really no stopping us.
Speaker 1 (20:40):
Right right, Sharon, Now, let's come to learn a bit
more from your books. Scaling with Soul. It's a nice name.
How how did you get down to this name? And
where did this soul coming into the picture?
Speaker 3 (20:55):
Well, we did use AI as a first pass for
coming up with titles, so that's one way that AI helped,
and I think they I think the AI brought up
scale and soul and we ended up putting them together.
But Scaling with Soul really refers to building and selling
(21:17):
a company, having a life changing exit without losing your
humanity when it comes to how you treat your customers
and your team. We built a phenomenal team, a happy,
productive team, and still had great business outcomes. And I
(21:39):
think that the whole title. And you know there's a
curse word in the sub head which you didn't mention,
and I won't mention here. But I'm in the Bay Area,
in the San Francisco Bay Area, in the center of
the entrepreneurial universe, at least in the United States, and
there's a lot of really bad behavior here. There's a
(22:02):
stereotype of the tech bro and people in the city
who are not in tech, they don't have a good reputation,
and there's a lot of bad behavior online by very
high profile entrepreneurs. And the latest example of that is
there was some proposed legislation in California called the Right
(22:23):
to Disconnect and it had to do with employees having
the right to unplug after five PM and on the weekends,
and some of the tech leaders here just went crazy
over that, and they were very hyperbolic about it. They're
going to legislate us into poverty, They're going to ruin innovation,
(22:44):
and blah blah blah. You know, you don't have to
put unreasonable demands on your employees to build a healthy,
profitable company. Our employees knew they were expected to unplug
after or five expected to take their time off, their vacations,
their weekends, their holidays, and we still were incredibly successful.
(23:09):
So I don't think it's one or the other. My
story proves that. And by the way, you don't want
to burn out your employees and lose them. We had
over a ninety percent retention rate. So I'm trying to
convey to entrepreneurs that they don't have to be jerks
or be adversaries to their own team to be successful financially.
(23:31):
It's just not an either or situation.
Speaker 1 (23:36):
Absolutely, Sharon, absolutely you said it right, And this thing,
this sort of empathy or understanding your employees better worklife
balance is so much needed in today's time, especially in
the backdrop of the great resignation and quite witting and
if they are not understanding, I don't know what sort
(23:56):
of a example it will set because it will create
hurdles rather than creating. Already the world is talking about
four de week, then that will be much more. Perhaps
those discussions happening. But in terms of you see a
lot of UH founders nowadays, especially in tech, they create
this company for you know, with the intention of selling it,
(24:19):
you know, so that there's nothing wrong with that with
a good, good exit. But as a founder, when you
are building a company and going for customer service, customer
value for the customer, and then there is a company
which comes in and takes your company and wants to
close it because it is competing with what they are doing,
(24:41):
and several of these these things as almost become a
non for for especially the big companies. How do you
see it? It means you have dealt You talked about
customer service. Initially you talk about the customer UH, and
there is UH and and then suddenly all that customer
is gone, uh for for the money, and then the
(25:02):
whole ecosystem is gone back to the same thing. The
big company does not worry about your customers, and.
Speaker 2 (25:09):
It is God.
Speaker 1 (25:09):
How do you see this sort of a culture almost
developing in especially in the tech tech industry. It is
happening also in the parma sector, but with a lot
of acquisitions happening in that and then the prices increases.
And I talk it because I see it more from
a India perspective, where people have limited amount of money
(25:33):
to pay for any particular product.
Speaker 2 (25:35):
But it gives.
Speaker 1 (25:37):
Undew advantage to some companies, make them so big that
they can rule over people's life. So how do you
see this part in tech? How do you look at
it from someone who talks about the customers?
Speaker 3 (25:51):
Well, that's a big question. And companies that are doing that,
they're just in a much different league than mine was.
That's you know. One thing that I heard recently is
that I don't remember the exact figure, but the amount
of venture capital that ends up with Meta, Google, Amazon
(26:16):
is astonishing. I think it was something like thirty to
forty percent of all venture capital just goes straight to
those companies because you have. The startups are all advertising, right,
and that is a problem. That is a big problem.
I feel like that's stifling growth in innovation itself. But
(26:38):
that's those companies are enormous and I would never claim
to know or play in those spaces, right. But with
my company that I built, when it came time to sell,
it was very important to me that the technology that
we that we built and the tool that we've bill
(27:00):
live on not only to continue to serve our customers,
but to have a place for our team to land
that would be a good place for them. And so
we had lots of conversations about that. If a company
had come to us and offered to buy us but
(27:22):
said we're going to just shut it down after that,
I don't know if we would have done that. I mean,
we clearly, my founder and I needed to exit for
our you know, financial freedom and future. We needed to
exit eventually, but we probably would have held out for
a different kind of opportunity because it was very important
(27:45):
to us to keep serving our customers and our team.
And fortunately, you know, euro money, it's now no longer
euro money. They've spun it off and the whole company
is called ultrata, But I'm hearing great things from both
our customers and our team in terms of what that
experience has been like for them. So that makes me happy.
Speaker 2 (28:10):
Absolutely.
Speaker 1 (28:10):
So when you talk about demastifying entrepreneurship, how do you
want the new age entrepreneur to look at this whole
entrepreneurship business as is it only about money or is
it about you know, some bigger motivation for some bigger purpose.
How do you how would you like to help them
(28:31):
understand how their entrepreneurship journey can be or should be.
Speaker 3 (28:38):
Yeah, it's about money and financial freedom, of course, but
it's also about the experience and what they can learn
and do along the way, and how surprising and rewarding
it other aspects of the journey can be apart from
(28:58):
making the money, you know, for me, one of the
unexpected joys of running the company was building the team
and watching especially young people just right out of college
or a couple of years out of college, find their
footing and start to contribute and start to grow into leaders.
(29:18):
That was wonderful for me to experience, and it's also
a great journey in terms of developing your own self
confidence and your own leadership skills, and just the knowledge
starts to become second hand. You don't have to think
(29:41):
so hard when it's time to make a decision. You
start to know what the right decision is based on
the way that you've been operating the company, what your
culture looks like that you've developed, and your own learnings.
You know, I made a lot of mistakes along the way,
but I learned from those mistakes and then I would
(30:02):
incorporate that into my leadership style moving forward.
Speaker 1 (30:08):
Absolutely, there is so much to learn from you, Sharton,
and a lot of people would like to connect with you,
want to learn from you, you know, want to read
your book. So what is the best way for them
to connect with you?
Speaker 3 (30:22):
Well, I have various ways. I do have a website
Sharon Ka middle initial kgillanwater dot com, and from there
they can find all my social media and my blog
and my newsletter and book announcements. The platform that I
use the most where I post not only everything I
post everywhere else, but I also get a little bit
(30:45):
more personal on is TikTok and my handle there is
Sharon Ka Gillan Water with two l's. And you have
to be careful because unfortunately I have a lot of
impersonators on TikTok so just look for the version of
me that has over twenty one thousand followers, and that's me.
Speaker 2 (31:07):
Wonderful, wonderful.
Speaker 1 (31:08):
With this, it's a wrap on this very special edition
of the KG Masterclass Life.
Speaker 2 (31:13):
Thank you so much, indeed for joining us.
Speaker 3 (31:16):
Thank you,
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