Unlocking the Power of Entrepreneurship: Turning Ideas into Profitable Ventures

Episode Transcript
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(00:51):
Aloha. Welcome. Inspired Money maker. Thanks for tuning in.
If this is your first time with us, welcome. If you're
returning, welcome back. Today we're diving into one of my favorite
topics. Entrepreneurship. Why? Because we're
talking about making money. I personally need to
refocus my time on how to make more money rather than

(01:13):
just saving money. So we all have different
money personalities and for me, I need to
balance that a little bit. A little too keen on trying to
squeeze a few pennies out when I could be making a dollar more on the
other side. So at its simplest, entrepreneurship is
when an individual or a small group strikes out on an original

(01:35):
path to create a new business. But let's be honest, it's so much more
than that. Entrepreneurship is innovation. It's job
creation. It's wealth creation. It's an engine
of growth that fuels entire communities and industries.
And for many of us, it can be a pathway to freedom. To take an
idea, something you've been dreaming about, and turn it into something

(01:58):
real, profitable and impactful. Whether you've
got a spark of an idea or you're already on the journey and looking
for the next push of inspiration, you're in the right place.
Today we're going to cover everything from validating and planning your business
idea to building a brand that people love, to funding
your growth, overcoming the inevitable challenges,

(02:20):
and maybe most importantly, creating a business with purpose
that does good in the world. And we've got an incredible panel
of entrepreneurs who've done it at the highest levels.
They've launched companies, scaled them, raised capital and
disrupted industries. You're going to want to hear their
insights, their wins, their losses, and the lessons that they've learned along the

(02:43):
way. So stick around. This is going to be a powerful conversation
that might just spark your next big move. Before we dive
in, I want to thank today's sponsor, Seeking Alpha. If
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(03:05):
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(03:26):
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(03:46):
Again, the link is InspiredMoney/alpha.
Now let's bring in today's expert panelists.
Let's see who's here. We've got Ilana
Golan, a serial entrepreneur, investor
and international keynote speaker who's done it all from
scaling startups to $15 million in revenue

(04:09):
and contributing to a $300 million
exit to becoming the first woman to train all
F-16 pilots in the Israeli Air Force.
Ilana now leads Leap Academy, one of the fastest growing
education companies in America and she's here to talk about
reinvention, resilience and scaling with purpose.

(04:30):
Ilana, welcome. Thank you so much Andy. It's great to
be here with everybody here. We're also thrilled to welcome back
James "Jimmy the Pencil" Orsini back on the show. He's
president of startup operations at VaynerX where he works alongside
Gary Vaynerchuk to scale some of today's most exciting
ventures. With decades of leadership experience in finance,

(04:53):
operations and agency growth, James knows what
it takes to to turn big entrepreneurial visions into thriving sustainable
businesses. James, welcome back.
Good to be here with your audience and seeing you again, Andy.
Also on my panel, my good friend and fellow
LinkedIn Top Voice, Nikki Estes. She's a serial entrepreneur

(05:16):
who co founded fintech innovator iCGpay, later
acquired by CSG Forte and now leads Market Me
More, helping B2B and tech companies grow through smart marketing and
sales strategies. She's the founder of Top Voices
Unite where she's built a powerful platform for thought
leaders and change makers. And she's here to share how collaboration

(05:38):
fuels entrepreneurial success. Nikki, thanks for
joining us from the water park. I
mean I can't be at home to do any of these kind of things. Like
it just doesn't make sense. Movers and
shakers right here now she could start moving at
any moment and I don't know.

(06:00):
Miki Agarwal is not here yet.
I hope that she comes in. I'm going to do just a quick intro.
Miki is a true cultural disruptor, a social entrepreneur,
investor and best selling author. She's built
category defining companies like Wild Finks and
Tushy, collectively valued at over 200 million.

(06:23):
Recognized as one of fast company's most creative people and a young
global leader by the World Economic Forum, Mickey
shares bold ideas and how they can become movements.
So let's hope that Miki will join us if not, we'll have
more room to go a little bit deeper into each
segment. But let's jump right in and go into segment one.

(06:46):
A strong business starts with validation. Market research
identifies demand, customer needs, and competitor gaps.
Entrepreneurs can analyze industry reports, conduct surveys,
and engage with online communities to refine their ideas.
Social media and niche groups provide direct feedback on potential
products or services. Developing a minimum viable product

(07:08):
helps test a concept with minimal investment. The
MVP should include essential features to gauge customer interest.
Tracking key metrics such as customer acquisition costs and
engagement rates determines viability. The Business Model
Canvas offers a flexible framework for structuring a business strategy.
Unlike traditional plans, it allows quick iteration based on

(07:31):
feedback. Entrepreneurs should also address legal
considerations including intellectual property protection and business
structure selection. A step by step validation process,
market research, MVP testing, business model
refinement, and legal groundwork lays the foundation for a
scalable, sustainable venture.

(07:56):
Ilana, you've reinvented your own career from fighter pilot
to tech entrepreneur to education founder. What's the
first thing you advise someone to do when they're trying to
validate a completely new idea? Oh, I
love this question. And thank you, Andy. So first of all,
I love the idea of this show because we are first of all

(08:19):
living in an era of portfolio careers and people
will have multiple streams of income, multiple ventures, and
you don't have to know everything. You just need to try
as fast as possible and
validate as close as possible to your clients. But it's. If I may,
Andy, I do have a funny story because sometimes we're so

(08:40):
attached to our MVP and to
the demo that we created or the idea that we had that we don't really
listen to what the audience says. And if I,
you know, a short story about it, we actually had a
company that my previous startup actually
that was supposed to be kind of a memory in your pocket and I was

(09:02):
really excited about the vision of it and suddenly somebody on
Facebook says, hey, I actually sold a house thanks to you. And I'm like,
you have a typo. Like there's like no
way with this app to sell a house. And you
know, and it took some time to, to actually listen and to understand that
there's, you know, there's medicine and there's vitamin and I

(09:25):
was creating a vitamin for others, but I was actually creating a
medicine for a certain group that later by the way
was acquired. So, so I think this is also like you
want to create MVP, but don't attach to it, like write it in pencil
as they say, because you might erase it
and kind of latch onto what the clients are audience is actually telling

(09:47):
you. Ilana, how do you know when to pivot
quickly based on that feedback or sticking to your
guns? Test, test, test, test, test. I can't stress it
enough. Like entrepreneurs, we have to be
relentless in testing and it is so
fundamental to work fast, hustle,

(10:09):
have a lot of chutzpah as I call it. In my case, I
actually found an incredible lady that was a real estate. I don't
understand anything about real estate. So for me this was a very, no
unknown area, but she was
leading a 30,000 people real estate
group on Facebook and I'm like, if I can get in front of her

(10:31):
so she can help me test this, if this is valuable.
And actually, you know, and I found a way to again, not pitch
but actually attract her to want to test
this with me. And again, it's all about how do you
create these connections and create this trust and you
know, short, you know, short story, you know, she created like

(10:53):
hundreds of people within minutes of, you know, that want to test this out.
And I was invited as a public speaker. This will,
you know, plan really well with your branding thing. But I was basically
invited as a public speaker in Inman Connect, which is one of the
biggest real estate conferences in the world. I don't know anything
about real estate, but I was in the keynote right in front of the

(11:16):
founder of Zillow and right after the CEO of Docuign.
And it looked like I actually know what I'm doing. So we were acquired. It
was funny. Nikki, what's your view
on testing an idea? Can you
leverage online communities and social media to help you do that?
Absolutely. So you need your beta testers. A lot of the technology

(11:38):
companies, they want to test this feature or that feature. My job was
to always break it. And so you can break
it so many times with the things you may think of. But reach out to
one of your community partners and ask them. So I'll send a dm, hey, will
you go to the site and will you try to break it? And by breaking
it, like test this link, test that link, go log in here. And so I

(11:58):
think that, and I would recommend to find those
people that know this is what you're doing. You're going to, you're going to
try to break it. That's, that's the goal. And then work around that, work
backwards so that you end up having this product that's a little bit more solid
before you go out to publish it to the real world.
James, the Customers or the clients that you work with, are they

(12:20):
testing those MVPs or do they already have that when they come
to you? You know, we try to tell them that
a dream without a plan is nothing more than a wish. So we do ask
that they have some form of business
plan direction that they're trying to move into.
We use a simple one page sort of summary format that's

(12:43):
generally accepted as a plan without being too
Draconian or inflexible.
You know, there's no shortage of ideas with the entrepreneurs that I work with,
the shortages in the execution. So, you know, we try
to just deliver tools that they can use like an
Eisenhower Matrix and helping them to prioritize and separate the

(13:06):
importance to just kind of keep them
on track with of those ideas.
Yeah. And give us some insight when you work with
those clients, how do you approach building operational
systems that can support rapid experimentation and

(13:26):
pivoting? It's what we call scalable
organization. We don't put the process in
because those keep breaking the process at each inflation
inflection point as a business grows, you know, 10 million, 20 million,
50 million. So we just trying to bring to them some scalable
organization that helps them

(13:48):
begin to scale the business and to
recognize also that their ability to
execute on what it is that they are
feeling, sensing and hearing from their audience.

(14:10):
Ilana, have there been times when
you had to pivot like 180 degrees?
All the time, I feel so, yeah. I mean,
first of all, I mean, entrepreneurship, it's going to happen all the time, but
honestly, in your career, you're going to pivot all the time. So I feel like
moving from Air Force to executive to

(14:33):
entrepreneurship to, you know, I studied electric engineering.
I am now running an education platform
which is one of the fastest growing private companies in America. It's like
all my life I feel it was one big 180 degrees. And I think
it's all about really tapping into what do you want,
what can you serve. That amazing combination, it's true for

(14:56):
entrepreneurship, it's true for your career, but what is that incredible
combinations of your skills, what you're excited about, what makes you happy,
fulfilled, what people are inspired by you. People are already intrigued
by you, what is it for, by your app or by your company, whatever it
is, people are already intrigued by something, what draws their attention.
And if you can pull all of these together, it's just incredible. I think the

(15:18):
hardest thing for us is to be honest with ourselves, honestly, Andy,
and, and to really look in the mirror and say, what Do
I actually want to do next? What is the true thing? Not because
society expects. Because
I sold my company way too early. And the truth is I was sick
and tired of it. Like, it sounds horrible to say it, but I

(15:40):
wasn't inspired. And on the other hand, Leap Academy right now is
my life. It's my dream. It's like I can't envision doing
anything else in my life. And it's just incredible to see thousands of people
change and life and careers change all the time and they. People figure out what
they want to do next. And so it's just incredible when you find
that zone of genius, whether it's in a company or in your career,

(16:03):
it's incredible the level of possibility that you can open up for yourself.
It sounds like no regrets, selling too early?
Oh, no. It's the best decision I've ever
done. And in fact, I chose it based on the people that didn't want me
to stay there. So. No, because when
you're tapping into what you really is, your zone of genius,

(16:26):
everything shifts and your life changes and you
find motivation to do the hard things and do it for your
entrepreneurship, do it for your career. Like, keep
finding that zone of genius, Keep finding that thing that
makes you unique. It's just everything.
Nikki, any story in your experience when early data

(16:49):
told you to either double down or to walk away?
Well, I'm going to build off of Ilana because when
we started our company, the FinTech iCG Pay, it was just
another thing that we threw out in the world. We had started out with something
we called MLS Atlas, where you could go and put a
house on a map geographically, right. And find it.

(17:11):
And then there was these details you could learn, like how many bedrooms there were,
how many bathrooms, you know, how much yard there was. We didn't
know anybody and we didn't have any money. And so we had to
pass that because that was such a big job. We had tested and we just
couldn't get enough people to join in a couple of years later. Have you ever
heard, I think you mentioned it earlier, Zillow? Yeah, that's not

(17:32):
us. You know, some dreams, you know, people said
that's the stupidest idea to put a QR code in front of someone's house
on a sign for them to scan. They're not going to do that because, you
know, 18 years ago we didn't have that kind of technology on our phones. But
my husband's like, pretty forward thinking, didn't work. And then there was
this other idea that we Had. It was fantastic. We have five kids and

(17:55):
so we would go to restaurants and there was always this huge wait. We're like,
wouldn't it be great if you could go onto a website and get
a reservation, you know, pick what time you want to eat, what you, you know,
put the allergies in or whatever, and then you show up and you know what
time you're supposed to eat. Again, we didn't know anybody, we didn't have any money,
so we dropped that idea. Have you heard of Open Table?

(18:16):
Not us. So I tell you that, like, some ideas
are great, you know, but they're just not for you. Maybe you're not in that
right community, but with iCG, you know, we still didn't have any money,
but we knew bankers. We had some good connections within the
check world. You know, we thought, what if, what if we
could get a check online, like credit cards? And at that time, people, they weren't

(18:38):
really excited about paying with a credit card online. And at that time, you remember
when you had to stick a desk in to update something on the computers?
Well, the idea was to go and make it virtually where we could update it.
And that was like, mind blown, you know. And so with the
evolution of that, people were like, so now I'm paying with a credit card online
and a check online called ACH. This is crazy.

(19:00):
But then we kept spreading it and it worked, you know, and we doubled down,
you know, we had more on staff and technology and over time, now
we're doing SMS messages where you, you pay by your phone. And it
was just, we had to see what was the market open for. So I think
that when you're having an idea, I would recommend that,
you know, it's. Your community is going to help you to test it. Is it

(19:22):
something that those people are going to get behind you? And if not, you know,
find someone that will or pivot and find, you know, what is it the people
around you need and then go forward with that.
James, what's your advice for entrepreneurs who are overwhelmed by
a perfect business plan myth?
I would say don't squeeze the baby too tight,

(19:45):
you'll choke it. Right. So part of what we like to do is,
I mean, look, social media has leveled the playing field, right? Why,
why build something you want to build? Why not build something that the
people want and need? And you can, you could listen
to it, you know, as. As it is on social media. You could test it
in social listening as well. So,

(20:07):
you know, there's a lot of people who have some Great ideas,
but it's, it's simply not easier than what we're currently
doing. It's not easier, it's not faster. So, you know,
this is why we're still tapping and swiping credit cards. Nobody has
come up with something that is easier than that at this point
in time. So, you know, it still looks like that when you're, when

(20:30):
you're at the point of retail. So, you know, you can't
get too passionate about the idea. The entrepreneurs
that are solving real issues are the ones that
I see that have the most success. You know, even in
the two examples that Nikki gave, you know, Resy was
incubated inside of the VaynerMedia hallways before it sold

(20:53):
to American Express. I mean, you know,
they were solving, solving an issue. People can't get into popular
restaurants and they wanted to find a way to do that. So
I think if you can lean into ideas
that solve concerns and issues that

(21:15):
happen right now. Look, you know, Uber is a time management
system. It just happened to be rolled out first with, you know,
transit and delivery service. But it saves time.
That's what it does. And now it's going to keep getting applied to more and
more things because it continues to save time. And that's the only

(21:35):
thing that we, you know, we don't have enough of.
Don't squeeze the baby too tight. I love that
advice. All right, let's, let's go to segment two.
Startups need a distinct brand identity to stand out in competitive
markets. A strong brand story connects with customers,
communicates values and builds trust. Consistency

(21:57):
in messaging, visuals and tone across all platforms
enhances recognition and credibility. Digital marketing is
cost effective when used strategically. Social media engagement,
SEO and content marketing help attract customers without high
expenses. Measuring customer acquisition cost and
lifetime value ensures sustainable growth.

(22:18):
Optimizing these metrics helps balance marketing spend and
customer retention. Community and influencer marketing amplify
brand awareness. Partnering with relevant influencers and
fostering online communities increase engagement. Customer
testimonials and user generated content enhance credibility.
A structured marketing roadmap, branding engagement,

(22:40):
lead generation and data analysis guides startups in
refining their strategy. By leveraging digital tools,
customer feedback and targeted content, businesses can
attract and retain a loyal audience while maximizing marketing
efficiency.

(23:02):
Ilana, I want to start with you again. How do you advise
entrepreneurs to balance their personal identity with,
with their company's brand? Oh, that's such a great
question, Andy. The truth is our brand, our personal
brand and business brand is kind of meshed these days.
And the more we going to go into the era of AI, it's

(23:24):
going to be more and more important for you to actually build your own personal
brand together with the business brand. You cannot
detach the two. And in fact, in the era of AI, you actually
there's ways that you need to build that personal brand, which is different than the
old, the typical only SEO, etc. Because it's not about
information anymore. The information is so easy to create

(23:47):
these days. So it is about communities, is about transformation. A lot of the
things that you guys, you know, mentioned, Andy,
it's just, it's really more about the transformation and the
communities that go along with it. But I will also say there's also
a really easy way for you to build a brand these days. There's
dozens of ways for you to build it, but there's also dozens of way for

(24:08):
you to test it and see if a concept makes sense. Like you can create
an, a website, a landing page and add with a little bit of
budget to see if anybody clicks. You could, there's gig economy, there's
volunteering. Like there's so many ways to check if, if a
message comes across the right way. So I think the more
you, you leverage that, the more important it is right now. And that's also

(24:30):
what's going to be the safety net for you to leap again, again between different
ventures, between different startups, between different whatever it is that you
want to create for yourself. Because again, it is going to be about
portfolio, it is going to be about multiple streams of income
and the way to build from one to another is going to be all
about your personal brand to move from one to another. So it's a great question,

(24:53):
Andy. James, VaynerX is known for helping companies
to cut through the noise. What's your process for helping
startups find the right message for the right audience?
You know, we talk about now brands being built on social.
I had worked at Interbrand, a great branding company
and back in that day, you know, there'd be half a dozen

(25:16):
executives sitting in a conference room and we would birth a brand and
then tell the world what that brand was. And
now, you know, the successful companies are
creating the brands that their consumers want.
So it's, it's automatic buy in if you will,
because you can do just that. And we're watching the

(25:39):
movement, you know that your, your video talked about SEO and you know, we're watching
it move from keyword, you know, to
phrases because of AI and conversations. And how do you,
you know, in the day you would type in couch and, you know,
get an ad for Huffman Koos or something like that serves to you.

(26:00):
But now it's like, I'd like to play board games with my family
around a fireplace. Well, you know, it's smart enough to know now you
may, you may need a couch to do that, right? So it's not waiting for
you to ask for that keyword anymore. And I think that's,
you know, you have to pay attention to where, where the, where
the movement is. Things are changing so quickly.

(26:23):
Nikki, how do you help brands align content strategy
with customer acquisition goals? So
I've went a little bit different of a route. As we sold
our iCG Pay, I wanted to continue with the marketing
route. And it took us a minute. There's lots of different agencies, right? You could
do SEO, you could do social media. But what I found is that as we're

(26:44):
coming back into the world, that stages is the place to go. So taking
that content strategy and using live streams like we're doing now,
puts out that education, builds thought leadership, gives information so that people
get to know you a little better. And then putting them on stage, like in
person, you know, which is kind of a, you know, used to be normal, but,
you know, now it's a, it's, it's becoming a relevant thing again that people want

(27:06):
to get on stage, they want to shake hands, they want to be in the
room with others. And so that's how we're pairing it together. So not only are
we giving them the opportunity to build their brand and, you know, as Ilana says,
with the personal brand and the professional brand, leaning on the
leadership that is going to be taking the live streams, but then we're putting them
in front of people and we're wrapping them up with social media. Hey, it's coming.
You know, this live stream is going to be there. Hey, we've got a blog

(27:28):
that's going to come out and then after it's done, we do a newsletter to
be able to talk about what had been talked about. Right. Or repurposing all of
that content. And I think that's really been the
catalyst for us going forward in that differentiator that,
you know, we're leveraging the voice. And as you know, you've seen, it's a Top
Voices Unite. Because the voices is the important part. The brand

(27:48):
leader needs to be someone willing to stand up and talk about what it is
that they do, which is hard sometimes for the tech guys, but I think
at this time and age, it's relevant. It's important. It's almost necessary.
I just want to tap into what Nikki said because I think it's so important.

(28:10):
Just because I think it's important to remember that in
2007 we all became a media company whether we like it or
not. So if somebody doesn't hear anything about us, the
assumption is that we don't have anything to say. And I
was always the humble person, quiet behind the scenes, going to work
hard. I was the computer person. Right. Like, but that's actually

(28:32):
wrong. And one of the biggest thing in Leap Academy is to help people elevate
their brand and continue using it to leap again and again. But the
beautiful thing is that, and this is tapping into what James said,
you don't have to have this massive influence anymore,
like in these days, but you do have to have a very specific

(28:52):
personal brand, whether it's through stages or whatever it is,
to actually leap and control the narrative of what do you want to be
known for? What kind of opportunities do you want? What kind of clients do you
want? Whatever. What are you trying to attract so that you can attract
the right kind of narrative. But it's incredibly incredible. Powerful way to
control the narrative. Super interesting. Yeah, we have

(29:15):
to. You're right. There's a tremendous opportunity when
we can be our own media company. But
then it reaches a point where you almost have to do
it. If everybody else, if the best are doing it, you better be doing
it too. Let's go
to segment three.

(29:36):
Entrepreneurs have several funding options, each with benefits and trade
offs. Bootstrapping allows full control but requires careful
cash flow management. It works best in early stages when costs are
low and revenue can sustain operations. If growth outpaces
resources, external funding becomes necessary.
Crowdfunding provides market validation while raising capital.

(29:58):
Successful campaigns require clear goals, compelling storytelling
and strategic promotion. Platforms like Kickstarter focus on
rewards while equity crowdfunding offers ownership shares to
investors. Angel investors provide early stage funding
and mentorship in exchange for equity. Venture capital
firms invest larger sums but often require rapid scaling

(30:20):
and significant ownership stakes. Understanding term sheets
and valuation is key before accepting equity investment
grants and small business loans offer non dilutive funding but have
strict eligibility requirements. Exploring alternative
options like revenue based financing or startup accelerators
can provide additional resources without sacrificing equity too

(30:43):
soon.
Nikki, you talked about having banking
connections. What funding stories
from your own ventures have taught you the most?
Bootstrapping. When it said bootstrapping it because

(31:04):
yes, it's difficult asking family and friends for money
is very uncomfortable. Going to the bank to get a loan is
uncomfortable. But I would say that bootstrapping
was, we learned a lot. We learned about how to spend money, how to budget
it well because the money was coming out of our kids mouths, you
know, so what we had to balance like hey, are we going to take this

(31:25):
vacation, you know, or are we going to go and double down because we need
some higher quality tech people. We want to hire the A players. So, so
for us that's where we are. We didn't have a big capital investment so
yeah, that's where we sit or we, we sat and then we sold and so
the next ventures again we're putting in our own money and
that's, that's it. Those are real life decisions.

(31:48):
James, what do you think is the biggest financial blind spot that
many entrepreneurs have? I think
it's their inability or lack
of desire to you know, establish a credit line if you're
actually up and running. Like I have so many people who are
willing to give up their equity in their company and I'm like wait a second,

(32:10):
you're running a, you bootstrapped and are now running a
seven figure profitable business. How come you're not just going to
get a credit line? Like you know, it's not brain
surgery. We did it for 100 years, just you know, do it now. And the
time to get the credit line is when you don't need the credit line because
that's when you can get it and when you need it, it's really hard. So

(32:33):
you know, just having them turn that on. I was, I was talking with an
entrepreneur yesterday who we did this several years back
when he didn't need it and now he's facing
you know, a little cash strapped lean time. But he's
had a history of viscerally knowing when to pour some
gasoline on the, on the fire when it comes to media.

(32:55):
And he's like, you know James, if only I had a couple bucks, you know,
I really believe in this thing. I'm seeing early signs of success in this,
you know, organic content that I'm putting out there. Maybe would it just a little
more paid media behind it on the META platform
I'm like just pull down on the credit line. And
he looked at me like I had three, three heads. I said listen, look in

(33:16):
the rearview mirror, give yourself some grace. You successfully done this
already. If you're feeling this viscerally this is, this is the unique part
about being a successful entrepreneur. Some of it is just you got it in
your gut. Pull down on the credit line, pour the gas on the fire
and let's watch the sales pop. And I
think, I don't know why he needed me to tell him that it's not brain

(33:37):
surgery but you know, he certainly felt better after that call and
I'm believing he's going to do just that.
It's a great point that you make accessing a
credit line over giving away equity in your company.
Just for the Inspired Money Makers out there. Go look up

(33:58):
Gwen Whiting, co founder of the Laundress, who was on the show.
I did a one on one interview with her and at the time when she
was trying to fundraise being a female entrepreneur,
she wasn't able to get any investors
so her only option was to use credit cards.
She's like she was just getting new credit cards all the time

(34:21):
so that she could rotate and access more credit,
which was extremely frightening at the time
or there were moments that were extremely frightening. But in the end when
Unilever bought her company, she and her co
founder owned 100% of the company. So
something to think about. Ilana, what are your thoughts?

(34:44):
I mean I love the conversation and I will be a little controversial.
I think at least in Silicon Valley we
became and again I raised money, I am invested in over
100 companies so I look at it in all direction and Leap Academy is
actually bootstrapped and became one of the fastest growing companies in
America. So I'm looking at it in all directions

(35:06):
and I think we started a society to
celebrate valuations and raising
funds instead of actually creating value
and you know, creating growth and revenue. So I think
we kind of missed up like there's a lot of room for funding and
there's some specific ventures that really cannot

(35:28):
lift off the ground without some venture capital. But I think in many, many
cases, if we gonna decide that we're not raising
capital just like Nikki and what James said, like we can
actually get a lot more creative about the funding, a lot more
creative about, you know, asking ourselves not I can't afford this,
but how can I create? How can I afford this? Right? And

(35:50):
I think as leaders there's also an element that we
need to kind of move from this ʻif then" mentality that we grew
up on like as kids, it's almost like if I get this, if I achieve
this, then I can get this or if I do this, if I get an
A, I can do this right? Like there's like an if then else thing. And
I think when you're bootstrapping or as a leader

(36:12):
overall, you almost need to flip it on its head and say, you
know, first I need to make this massively scary decision of
putting things on the card. And, and I will see the ROI way
later. So it's a... Suddenly you need to say yes
to the maybe and see the results later. And that's a very
scary thing. But honestly, as a leader, you're going to have to, you're going to

(36:35):
hire before you're going to see returns. You're going to raise capital, you know, you're
going to, you know, have pay for ads before you're going to see
returns. You know, there's always this like chicken and egg. But
it's all boils down to you believing in yourself and believing
that what you're doing actually makes sense. And
with that and tapping into that, just like James and Nikki talked about,

(36:56):
tapping into that, you know, there's, there's endless
possibilities.
I want to jump on that. So my husband started with a job. He,
he worked for a gas company with welding and handled their technology.
And he said, I really want to take this, like, full time. I want
to run this technology company. I think I could do it. Will you believe in

(37:18):
me and take that risk? And I was like, sure. I mean, you know, what
do we have to lose? We at least attempt it.
We're young, you know, why not? And I got a phone call from one of
our family members telling me how terrible of an idea it was. Don't do it.
It's a great job. You've got benefits, you know, you've got these kids to think
about. But we did it, you know, and you had to keep

(37:39):
having those risks. Okay, now we're doing well in business, right? And you
see that so many times. To where people are like, I don't know, is it
worth the squeeze to be able to do that for our
family or for the future? And it's really cool when it works
out. The mindset of the entrepreneur, they're going to
do it again if they fail. But you don't know. You have to fail

(38:01):
fast and then just keep attempting, keep going, keep progressing.
I love it. Ilana.
Thank you. I love that.
With that, let's go to segment four.
Resilience is key to navigating setbacks. Entrepreneurs

(38:22):
should reframe failures as learning opportunities, analyze
mistakes, and adjust strategies without losing momentum.
Maintaining motivation requires setting clear goals, celebrating
progress, and staying adaptable in a changing market.
Time management is critical for efficiency. Prioritizing high
impact tasks using methods like the Eisenhower Matrix or

(38:43):
Pomodoro technique helps eliminate distractions.
Task automation and delegation prevent burnout and create space for
strategic decision making. Building a strong team fosters business
growth. Effective hiring, onboarding and delegation enhance
productivity while a collaborative work culture keeps employees
engaged. Scaling sustainably requires monitoring key

(39:05):
performance indicators and optimizing processes. Preventing
burnout involves work, life balance, stress management and mindfulness.
Entrepreneurs who embrace adaptability, resilience and smart
delegation build businesses that can thrive through challenges, ensuring long
term success without sacrificing personal well being.

(39:29):
Ilana, can you share a defining failure that later
became fuel for your success?
I mean, I think I can write a whole book on failures and actually by
the way, Gary Vee, James, is blurbing my book, so I'm very
excited. There's going to be a lot of failures on the book, but I will
share. So in

(39:52):
a previous company, actually I was already kind of in
corporate, kind of what Nikki said, like I started in corporate and kind of move
up the ladder and, and at some point
I was already vice president doing some big thing. But a friend of mine said,
hey Ilana, do you want to start a company together? I knew him for two
decades. I was like, oh my God, this is going to be a dream.

(40:13):
We started the company and you know, we even raised capital.
You know, they were evaluating our little baby at $5 million. The
typical shiny object Silicon Valley story.
And it was time for me to leave the VP
role and say goodbye. And I told everybody about the startup.
It was so exciting. Within 24 hours,

(40:37):
my co founder decided to take the money, throw me out of the business. And
I was left with nothing. No job, no salary, no startup, no
investment. And the worst of all is your ego. Your ego just
crushes down the drain. I'm like, I told everybody about this
and I think it was the first time that I realized my identity was always
attached to my title. It was attached to my company. It was like

(40:59):
I was the title. Like I never even built myself a brand.
I never thought of who is Ilana without the title. And,
and it felt like I was complete nobody. It felt like the worst failure on
the planet. And I think the, the hardest thing probably is not
knowing what I wanted to do next, which is for somebody driven and high
achiever, it's like, why do you not know? Like everything was scripted in my

(41:23):
life. Like I always knew what's next. How can I be so confused?
But I was overwhelmed. And I think that that
basically it was one of the hardest time in my life, I couldn't sleep at
night, I was snappy at my kids, my health deteriorated. Like, I can go on
and on, but I think in hindsight this is, this was the seed
for Leap Academy because at that point I was like, am I the only idiot

(41:46):
in the world that doesn't know what they want to do and that they're, you
know, need to like, fast check their career? I don't want to start from zero.
How do I solve this? And you know, to those listening, I
want to say, like, sometimes your biggest challenges are exactly
the fuel that you need to do. And it's exactly the seed that you
need in order to take yourself to the next level. And this is your calling,

(42:08):
this is the big thing that you want to do. And because that
becomes your fuel. Because entrepreneurship will still go up and down. But if you
have like a really strong why, it's everything.
Like every time I go through a hiccup, a challenge now with sleep, I,
I'm like, I know why I'm doing this. Like, I want to see high achievers
driven people leap in their careers in ways that they didn't know

(42:31):
is possible. I want them to get the clarity. I want them to open the
brand. I want them to leap to some incredible things that they didn't even know.
I want them to open these portfolio careers for themselves. So that's my
soapbox, Andy.
I love it. I imagine it must have been very difficult to
pick yourself up after that and then, oh man, to get on the horse

(42:53):
again. So kudos to you. Thank you,
James. Clearly we hear entrepreneurship, it is a lot
of ups and downs. What systems do you recommend
for staying aligned during chaos?
You know, it's, it's kind of what Nikki said about the
fail fast fix fast learn fast. And that's, that's what I've seen with

(43:15):
a lot of entrepreneurs. Entrepreneurs are not afraid to fail. They learn more from
their failures than they do from their successes. I'm glad
your video talked about the Eisenhower Matrix. I can't speak enough about that
and the ability to separate that. In fact, in Medium,
I had written an article years back when
Gary asked me to start the Sasha Group, a small

(43:38):
medium business that was targeted to small, medium sized and
challenger brands that at that time we had built a company to service Fortune
500 in VaynerMedia. We didn't have an offering like that
and you know, we, I pride myself on the fact that I ran it
for five years profitably every year of its
existence. So Gary actually referred to it once as a start right, rather than

(44:00):
start up. But, you know, we talked about, you know,
hitting a certain revenue goal in year two. And
I didn't have, I didn't have client names to associate to the
goal. So we prepared an Eisenhower Matrix. And I was like, listen, I
think if we do these 12 things over next year,
you know, we'll get to that revenue number. And you know, if

(44:23):
you know anything about an Eisenhower Matrix, it's four quadrants and you know, it's
urgent. Important. Some things are urgent and important. Some things
are neither urgent nor important or nice to have. And we
place those dots and he moved a couple of the dots. This
one's a little more important for me, this one's a little less important for me.
So therefore, now he owned the roadmap that I created

(44:45):
and I brought it back to my leadership team and I delegated. Okay, we're going
to do all this, and here's who's going to do this dot, and here's who's
going to do that dot. And based on their placement, some were going to be
done the first quarter and some were going to be done the third quarter. And
I'm happy to say that when we, when we purposed for profit
and we looked in the rearview mirror, we had done exactly what we said we

(45:06):
were going to do through this Eisenhower Matrix. So I, I
have a video on it in YouTube as well, you know, and how
to use it. I gotta find it and look for it. I love that it
gives you a framework to prioritize. It's
really the four quadrants end up being like do, plan,
delegate or eliminate. Right? Yeah, well, you

(45:28):
know, I've used it for client plotting graphs. I've used it for
decision making opportunities. You know, it's to
help you. If there's 12 things to do, they're not all
of equal weight. That's the, that's the notion of this thing, right? If
there's 12 clients in the building, they're not all of equal weight. There's,
if you use it for clients as an example, and the X and Y axis

(45:50):
is dollars that they bring in and marquee value
to the agency. You know,
there's certain seasons when you know you're in a different
quadrant, like, hey, in the second, you know, this is okay
to do in the first quarter because by my hope is that by the end
of the year becomes a bigger client, it'll move up to a different quadrant.

(46:12):
And then there's some where, hey, look, nobody's heard of this client but it's big
money and we're in the third quarter now. We're trying to make our figures. So
money's green. So nobody cares, you know, what the name of the client is
as long as they're paying. So, you know, there's so many different ways that you
could use the Eisenhower Matrix to help in your decision making
process. Nikki, five kids.

(46:33):
Even today you're running multiple ventures
simultaneously. How do you avoid
overwhelm? Did I say
that I have avoided it? I didn't say that.
I'm not there yet. Don't put me there. No,
it's just a day to day. That's. That's all we can do is just one

(46:55):
day at a time. One moment is necessary. That's. That's how we've
pulled through. I can't give advice on that just
yet. But that's how you juggle. That's why you're in the car. Like,
you're a master in juggling. Like, seriously, like, this is
impressive. Like, this is it. Like, you just find
a way because you're never gonna have it all at the same time.

(47:17):
You can have it all, just not at the same time. So you're doing phenomenal.
Thank you. Yeah, we. We just. We don't quit and we. We
just put different fishing lines out there, you know, and this is why we
homeschool. We've global schooled with the children because we want to
do great things and so we want them to be exposed to it along the
way. And it just. It just takes maybe giving up sleep this day,

(47:40):
maybe giving up something another day, but it. It balances out. It's a good life.
I feel overwhelmed just watching you from a distance. Nikki,
do you ever struggle with burnout and how to manage that?
I would say probably about once every three or four months.

(48:00):
We gotta go and do something for a weekend. My husband and I'll go and
just take a weekend. We sleep, we play. That's how we
just do it. There's this road. So I live in Fort Myers right now. I'm
in Cape Coral, Florida. And there's this road called
McGregor Boulevard. And so we'll put the sunroof open. I
put my hands out, you know, as we go down a lined road

(48:21):
full of. Or I'm sorry, it's a road lined with palm trees.
That's a reset for me. You know, we're right on the way to the beach.
We're talking about things, we're praying through things. We
just have to do it so we can keep moving on. You can do it,
Andy. You just have to reset your mind and think about it. Fine. All right.
I'll stand out of the sunroof and see what happens. How about you, James? Any
advice? I have back issues, so I don't stand

(48:44):
out of the sunroof anymore. But, but it is. What
I tell the entrepreneurs that I work with is that
you have to fight for the balance. And it is a
fight. You know, your, your work wants you 100%.
Your kids and family want you 100%. Your
philanthropic endeavors and church and not for profits want you

(49:06):
100%. And you have to really fight for, for
that balance. But it is possible.
You know, you're talking about a 40 year career and you know, I'm leaving,
you know, for a family vacation. We're still doing it with, with adult children.
So, you know, we, we, we make it work
and I'm all the more better for it now. How do I do that?

(49:30):
I'm the same person in every environment. I'm the same guy
in my house, I'm the same guy at work, I'm the same guy at church.
I don't wear different masks. I can't change who
I am. So by being consistent in who
and what you're getting, I could do a lot
more than I normally would by being

(49:53):
different people in different environments. So
be genuinely yourself. Let's bring it home and go to the last
segment. Sustainable businesses
prioritize long term impact alongside profitability.
Entrepreneurs can reduce environmental footprints by optimizing energy
use, sourcing responsibly and integrating circular economy

(50:15):
principles. Transparent supply chains ensure ethical labor
practices and sustainability with technology enabling real time
tracking. Social entrepreneurship aligns business goals with
positive social or environmental change. B Corp
certification and sustainability reports validate impact while
ethical marketing avoids greenwashing and respects consumer privacy.

(50:37):
Funding options such as impact investment firms and social
entrepreneurship grants provide capital aligned with sustainability
values. Measuring and reporting impact builds trust with
stakeholders. A business ethics playbook helps maintain
integrity. Clear values, ethical supply chains, responsible
marketing and transparent reporting ensure accountability.

(50:58):
Entrepreneurs who integrate ethics into decision making create businesses
that thrive financially while making meaningful contributions to
society and the environment.
Ilana, I know that you have limited time with us. Tell us
a little bit how you help people to design careers or ventures

(51:22):
that align with their personal purpose. Yeah, I
mean, I think the beautiful thing is and, and I think you talked a
little bit about burnout in the previous question. And I think a lot of
burnout comes when you're not in peace with what you're doing,
which is kind of what the others talked about, but also when you're not creating
real impact and things that matter. And I think the more you can

(51:44):
rely on the things that actually matter, the more is going to
motivate you to keep on going and to do
better. Right. So I think for me it's really about not
only creating it for myself, but I want thousands of our
clients to create life that matters and that
creates the life that they want to create. And sometimes it

(52:05):
is impact, sometimes they want growth or money or whatever it is. But
I do believe that when you can actually make a difference in people's lives,
you can actually go further. And there's nothing stronger than
either a person that says thank you, thank you changed my life, or
an organization or knowing that you're actually making a

(52:25):
difference in society or the world. So I think
that really is becoming the fuel that you need in order to create change.
I love the idea. Whether it's you or a company,
the power of doing something bigger than yourself is huge. Exactly.
Yeah. James, have you seen impact driven
startups outperform purely profit driven

(52:48):
ones? Well, it's funny you said, I met with my financial
planner yesterday and he let me know that one of the highest
performing things in my portfolio was the
sustainability type investments
that I had, which actually my daughter picked all those
investments so I can't take the credit for it. But

(53:10):
yes, that does perform. One of my favorite entrepreneurs
that I've been working with both at the Sasha Group
previously and now at the Vyve
Leadership development training has a sustainable
organic pesticide type company
out of North Carolina that repels

(53:32):
rather than kills. And you know, her
father was a former sold chemicals and she
purposed to do the exact opposite. And it's a very
successful business and the products work
well and you know, she gets on
some speaking engagements. I have another colleague who runs

(53:54):
sustainability for Oregon State College. And
you know, just, just a lot of
entrepreneurs in my world who play in that,
in that arena and even when business is tough, they're
smiling. Love it.

(54:15):
Nikki, you've built communities that emphasize collaboration and
purpose. How can entrepreneurs lead movements,
not just companies? It's a good question.
I would recommend that they have the same heart.
They have to ask questions just like you would when you want to sell someone
a product. You're selling the service of your heart.

(54:38):
And when they're working together with the community
and they're on the same page, they go a lot farther. So like James had
talked about, you're the same person when you're at work, you're the same person when
you're at home, you're the same person when you're at church. Like, that's important. So
then when you're talking with people that may be at church or at, you know,
in your community, you could do business together with them because you have

(54:58):
similar values. And then those people that, you know you're doing work with,
maybe there's a philanthropic that you're a part of. Well, they know
that this is something important to you because you're the same guy. You think about
sustainability when you're at work. All right, well, what else can we do in the
community? Hey, you guys want to go do an ocean pickup? You remember
Edo Perry? You all did a live a couple months ago, and

(55:20):
that's. He's the same guy. He wants to be able to make a change, you
know, for the climate in a way that's profitable, for not only
the money in the pocket, but also for our community. So
doing things like live streams, doing things like getting on stages,
you know, I think doing roundtables, you know, entrepreneurs can come together and
have these kind of conversations. And I believe that that

(55:42):
creates a movement because you're putting it out there. You have to speak up.
It's not 2007 anymore, right, Ilana? Like, we have to
speak up. We have to say what's on our hearts, we have to say what's
important to us, and then we can create a movement with that kind of collaboration.
Ilana, we kept you to the end. I think you have to hop. You want
to leave us with a closing thought before you go? I mean, I love

(56:04):
this conversation. I really enjoyed all of you and listening to
you and. Great question. In moderation, Andy. And
the one thing that I like to kind of think about is
in Leap Academy, we say it's not about what we make, it's what we make
possible. And I think the more as entrepreneurs, you can think about
what are you making possible for others, for the world, for society, for

(56:26):
yourself? It doesn't matter. But what are you actually making possible? And
the more you're relentless about it and you're chasing that dream,
it's amazing what you can achieve. Well, thank
you. Thank you. Thank you, Ilana. Thank you, James. Thank you, Nikki.
This has been an incredible conversation, and one of my
favorite takeaways today was this. Every

(56:49):
successful business starts as an idea, but it
only becomes real when you take that first step, even if it's small,
whether it's testing a minimum viable product, building a
community around a brand new or Reframing failure as a lesson
Our panel reminded us that progress comes from action,
not from perfection. So here's my challenge for you this

(57:12):
week. Take one concrete step toward your idea. It
could be writing out your business model on one page. Maybe it's reaching out
to somebody in your network for feedback, or even setting aside
time to research your market. Commit to taking just one
step, because the difference between a dream and a business
is the action that you take today. If this episode sparks

(57:35):
something in you, share it with a friend or leave us a review and let
me know what step you're taking. I can't wait to hear about the
business that you'll build. A few things before we part ways.
Let's connect on LinkedIn Find me by searching for
"Advisor Andy." Inspired Money is created and produced
by me and Bradley Jon Eaglefeather. Bradley is behind the

(57:57):
scenes during the live stream. He edited segments. Chad
Lawrence does our graphics, animations and editing. And last
but not least, I want to give a big shout out to our amazing
guests. Go follow their work and keep learning from the best.
Ilana Golan, who dropped off. She's a serial entrepreneur and
founder of Leap Academy. You have to subscribe to

(58:20):
her YouTube channel. Just search for Ilana Golan Leap
Academy where she keeps really good company. She's interviewed
Gary Vee, Richard Branson, Daniel Pink.
I really need to get her tips for booking these top tier
guests. Check out her programs and speaking
engagements at ilanagolan.com. James

(58:41):
Orsini, President of Startup Operations at VaynerX.
Discover more about the work that he's doing at Vyve, a
high performance acceleration program at
VaynerX. You can find out more at
vaynerx.com. And Nikki Estes, serial
entrepreneur, CEO of Market Me Moore, founder of Top Voices

(59:02):
Unite. You can connect with Nikki on LinkedIn. Look
up Nikki Estes or her community
marketmemore.com. Anybody want to plug anything
in particular? No, I'm just happy to share
that the Vyve Initiative for Leadership. We do
have a lot of entrepreneurs in there and we cross pollinate

(59:25):
Entrepreneurs and Fortune 500 marketers and leaders
and it's a really interesting learning session.
Vyve by Vayner. You can find it on LinkedIn and Instagram as well.
Love it. It's got to be such a high energy and creative energy
there. Yeah, yeah, absolutely.

(59:46):
When is it? How can we learn more about it?
Learn more about Vyve, you mean? Yeah, yeah, yeah. I'll. Well,
I'll make sure that we, we tag it here in the show notes but
it's, it's under the vaynerx.com
website as well and it's, it has its own

(01:00:08):
social channels and in both LinkedIn Vyve by Vayner and Instagram
as well. Okay, Andy, that's a way that we can plug in
some of these voices that we associate with from the Top Voices Unite community,
plug them into good resources for their growth.
Fantastic. We will definitely do that. Be sure to
follow all of our guests today. They're doing amazing things that can

(01:00:31):
inspire and elevate your own entrepreneurial journey.
Inspired Money returns next week. I think we're planning for Wednesday.
That's August 13th at 1pm Eastern. Our topic is going to be

Sustainable Investing (01:00:43):
Investing with Purpose and
Impact. It should dovetail very well with today's
discussion. Thank you for listening for watching. I
look forward to seeing you next week. Until next time, do something that scares
you because that's where the magic happens. Thanks everybody.

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