Episode Transcript
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(00:00):
One of the key reasons why companies fail
(00:02):
is because of co-founder splits.
Fundraising is an art and a science.
It underpins the ability to sell.
You can have the best products in the world,
but if you're not focused on distribution and sales,
it won't matter.
Being creative can save you a lot
on customer acquisition costs.
The best time to meet investors is when you're not raising.
If you look at Sarah Blakeley, founder of Spanx,
(00:25):
she never worked within fashion.
However, what they did have is lived experience
of the problem they were solving for, which is...
Welcome to The Startup Leap,
the number one podcast interviewing startup founders
who have taken the leap.
On The Startup Leap, we hear real, raw,
and relatable stories of how they've navigated
taking the leap, were your hosts.
I'm Yvonne.
And I'm Maria.
(00:46):
And this is The Startup Leap podcast.
Any statements made by Maria, Yvonne,
or The Startup Leap guests are solely their view
and are not advice.
Hey everyone, welcome back to The Startup Leap,
where we share real stories and lessons
with founders who have taken the leap.
I'm Yvonne.
I'm Maria.
And today we're gonna be talking about
something really critical,
(01:07):
especially for first-time founders.
The five biggest mistakes first-time founders make.
Now, if you're launching a startup,
this is probably one you want to stick around for.
To pretty much hear the mistakes
that you would want to avoid
as you launch your first startup.
Yes, so why are we speaking about this?
If it's your first time, Maria and I have evaluated
thousands of startups invested over $200 million
(01:29):
in companies and invested in over a hundred startups
across Europe and Africa.
So we are bringing those perspectives
into the conversation today.
Yvonne and I have seen a lot
and we're gonna be tapping into the real life experiences
of our perspective looking at startups.
This video may have something good for you.
So stick around to find out.
Also, we have a bonus at the end.
(01:49):
So without further ado, let's dive in.
Maybe the first one is selecting a profit problem.
If you have started building or you're in the tech space,
something you would have heard of is under market fit
or problem founder fit.
All of this is just to say that
in this world today or 2025,
what we are seeing is that it helps to have
some kind of congruence with the problem.
(02:12):
As a founder, as a builder, as an innovator,
you are likely to spot problems
that are potentially opportunities.
There are several founders who are tackling problems
where they don't necessarily have a direct experience
or insight or approach that might be unique to the market.
So it's just mostly passion and not necessarily skill
(02:34):
or expertise or unique insight that makes it less hard
to tackle the problem.
Yeah, I mean, if you think about second time founders
as well, they tend to be very deliberate
about the opportunities they chase,
ensuring that in lines of their experience, network
or industry knowledge and passion,
they really leverage their previous lessons
and avoid pitfalls that really focus on something
that's gonna be scalable, high impact
(02:55):
and generate outsize returns.
Having said that though, there are a number of founders
who don't necessarily have a fit
with the problem they're solving.
So if you look at Airbnb, for example,
Brian and Joe had no experience within hospitality or tech.
If you look at Sarah Blakely, founder of Spanx,
she never worked within fashion.
However, what they did have is lived experience
(03:17):
with the problem they were solving for, which is really key.
If we think about that, those founders built
in a different time from now, it was 10, 20 years ago.
We could argue that maybe that time,
the talent that you even needed or the experience
you needed to build a tech startup was just starting out.
So in the case of Airbnb, for example,
(03:37):
there were very few like really massive tech companies
of that type in the industry.
So they probably couldn't get experience,
they needed to be the pioneers.
But now today you have this backlog
of incredible innovators who've built incredible companies.
So now the bar is a bit different.
You can build a company even without having direct
experience in that company.
(03:58):
Many people have done it.
The thing to note is probably gonna be harder
to raise funding because most investors really,
really over index right now on you having some type
of experience or it's gonna just take longer
to get people on board.
So for example, if you know the story of Airbnb,
they didn't have it easy.
I once met an investor who was at the pitch
(04:18):
with the Airbnb founders.
Like he remembered he was telling me and he was like,
Maria, it sounded crazy.
But I think just to note there is that if you do decide
to tackle an industry where you don't have experience,
I think just get ready for the uphill battle
of getting people on the line.
You need to be incredibly resilient.
Your willpower needs to be incredibly strong
because it's probably gonna be hard.
If you read the story of Sarah Blakely,
(04:40):
of the Airbnb founders, about the Slack founders
who also don't have experience,
they went through a very tough road.
So it's not impossible, but it just makes it less hard
if you have some experience and fits with the problem.
And there's something called the concept
of a right to the problem.
I heard this once about four years ago at a conference
and it really stuck with me.
And it is the idea that a problem exists,
(05:02):
but there are many people who can tackle it.
You have to have a right to be the one to tackle the problem.
What's your right to the problem?
Why you?
Is it your lived experience like Ivana said?
Is it your background?
Is it your experience?
Is it a unique insight?
Because you've been in that industry for so long,
you know something that anybody who's looking outside
in might not know.
Yeah, and I think if we look back
on some of our previous episodes,
(05:23):
one great example is say he worked
within the logistics space.
However, he stumbled across a mental health startup,
realized very quickly that that wasn't where he had an edge.
And so he went about, got some more experience
within the logistics space before founding his own company.
And I think speaking about that right to build
within that space, I think it's just really helpful
(05:45):
if you do have that unique insight
and experience within the space.
And if not, then just go very deep, immerse yourself,
speak to customers and just fully know everything you can
before jumping and building.
Absolutely, absolutely.
Mistake number two is building a complex first product
without the customer.
One of the common themes that has really come across
(06:07):
in all of our episodes is how the founders
have really spent time immersing themselves
within the industry and knowing their customers.
Before you get caught up in the big vision,
assuming what you think customers want,
adding features that you think customers want,
rather than really validating it with users,
you really just wanna spend the time with customers,
(06:28):
whether it's doing round tables with them.
Great example from one of our previous episodes
is Michelle Kennedy, founder of Peanut.
She literally went and went to parties,
gave out rave stickers, just to get a sense
of what it was that mothers wanted
before she went out and built Peanut.
I think Yvonne, you've said this on several episodes
in the past, spend time with the customer.
(06:49):
In the initial stages, when you're building something,
there's that dopamine and euphoria
of building something new that can really cloud our judgment.
In my experience as an investor,
I've seen several founders who've gone to markets
with a thesis that they think is correct
and they don't demonstrate that depth of understanding
from the customer.
I like to hear founders' philosophical views
(07:12):
of why the customers are using what they're using.
It shows a level of understanding
of the subconscious desires of a customer.
And I think this is even more important
in consumer products, because the best consumer products,
they're cult-like, they're belief systems.
People love them or hate them.
One mistake to try to avoid is not spending enough time
(07:34):
with the customer to knowing who they are
and projecting your desire on what they want
and as a result, building a complex first product.
If you are a builder especially,
there's a tendency to remember that feeling
of your first product, oh my God, the pages,
the logo, the icon.
In my experience, with the best founders,
they don't obsess on building that first product.
(07:56):
Even if you are a builder at heart,
you almost need to realize that
if you build a perfect product
that a customer does not use or want, it's zero.
So you really need to anchor on the customer
and avoid building a complex first product.
We've also talked about this on previous episodes actually
on how to think about that initial customer validation
and really holding yourself back
(08:17):
from building the first product.
And like I say, the best founders often sell the products
even before it's built.
Yeah, 100%.
Work on a very simple first version of your product.
It can be super scrappy.
We've had founders come to the podcast
who have literally built their first version of the product
in Excel, in WhatsApp, and avoid building
like a full-blown product because what does that mean?
(08:39):
So you don't wanna go about building an expensive product
that essentially no one wants, right?
So if you can do it in a very lean, scrappy way initially,
get some validation and then build,
that is the smart way to do things.
Talk to those potential customers,
involve them deeply in the first build of a product
and focus on solving one core problem if you can.
Go back to Robin AI's episode
(09:02):
with founder Richard Robinson
where he shared how the first version of the product,
him and his team were literally reviewing the NDAs themselves
and it took some time before they fully automated that.
So remember, go simple with the first version
and build with your customers.
Absolutely.
And the next thing I guess to think about
(09:24):
that is a very common mistake is giving away
the incorrect amount of equity.
And I say incorrect because you can give away too little,
you can give away too much.
Some people really talk about the too much
without the too little or talk about the too little
without the too much.
Now we've had an episode with the founder Elizabeth
where she gave out too much equity
in her startup at the earliest stages.
(09:45):
And some of the time it's because you don't quite know
what the benchmark is.
If this is an episode you want us to touch on,
please let us know in the comments
and then we will try to do a double click on this.
But the thing about giving away too much
or too little equity is on one hand,
if you give away too much equity,
you make your startup uninvestable.
The way VC works and we've done an episode on this
is that you are giving away pieces of your company
(10:06):
for growth capital that allow you
really reach those supercharged outcomes.
Now, if you give away too much of it,
there's just not enough room to give to other investors
and you've given away too much for a little,
for a small price.
That's the first thing.
Then the second thing is even in VC
for later stage investors series A and above,
they do have thresholds to which they require
the founders to have ownership.
(10:27):
Because that's the only way they can rationalize
that you will stay in the business
and you're incentivized to continue to building the business.
If you have too little ownership at the early stage,
then why are you building?
Because if you build,
oh, I'm not gonna benefit from this at the end of the day.
So you're probably not gonna be as incentivized.
So that can create really tricky technical issues
on the fundraising part.
And then on the too little side,
people don't talk a lot about this,
(10:48):
but as a founder, there needs to be a balance
between how you protect your equity and how you give it out.
You should definitely not give out too much equity,
but you also, if you're thinking of a venture backed outcome,
you will need to concede some equity for capital
to be able to grow.
Absolutely.
I think a really good rule of thumb
is to just be really strategic,
create a clear equity split plan
and think about a vesting schedule
(11:10):
to protect everyone involved.
So the way in which vesting schedules work
is typically it'll be over a four year period
with a one year cliff.
This really means that founders do not earn
any vested shares until that one year cliff period.
And after that point,
they then begin vesting their shares
on a monthly or quarterly basis over a three year period.
And I think that's really helpful.
(11:30):
Typically, sometimes that happens
at every single time you fundraise.
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Typically, sometimes that happens
at every single time you fundraise.
(11:52):
So if you raise seed round, if you raise series A round,
you may have to revest those shares.
But I think it's just a healthy way to ensure
that everyone that is allocated equity
is also incentivized to have that long-term skin in the game
and to work on the bigger picture
and be along the journey for the ride.
Absolutely.
(12:12):
And I think even beyond equity itself,
one thing people don't really talk about
is also the early hires and the stock option plans
just to incentivize people.
Even if you have fundraising dollars,
you really want to have a heavy equity compensation
for your early hires
because those incentives need to be right.
Also, beyond just the quantity of equity you give away,
it's also the legal agreement.
I've seen founders who have gotten into
(12:34):
a very tricky situation with liquidation preferences
and many terms that are inserted into their agreements
at the early stage that just make the startup
uninvestable in the long term.
So it always helps to have a legal friend on tap
that you can quickly just call.
Because, you know, we're not lawyers.
You're not a lawyer as a founder.
So it does help to have a lawyer
(12:54):
explain what the implications are to you,
what they consider standard in the market,
especially when your investment documents are non-standard.
So maybe it's not a safe or an ASA or et cetera.
That's another thing to think about.
Now, another thing that I would say is a big mistake
is you can have the best products in the world,
but if you're not focused on distribution and sales,
(13:15):
it won't matter.
Now, it's often said that first-time founders
focus on products,
second-time founders focus on distribution.
And this is something that I have witnessed.
A recent example is Founder of Granola,
which is an app that I absolutely love.
It's one of my apps for 2024.
And essentially the founder actually previously
founded a journaling app.
However, he decided to pivot away from that
(13:37):
just because he couldn't figure out the distribution.
So if you can't figure out distribution
for the product you're building, there's a problem there.
And you should really think about distribution
as you think about building the products
and who you want to serve very early in the journey.
When we talk about distribution,
it's essentially how do you acquire customers at scale
(13:58):
for less than they're able to bring to you
with really strong margins.
So even as an investor,
we invest very much in the early stage.
At the earliest stages,
it's really about the team and the go-to market,
and of course the broader market opportunity.
The founders who tend to think of commercial, analytical,
very precise ways of how they get their product to market
(14:18):
tend to have these really strong outcomes
because they've begun with the end in mind.
They're like, okay, how do I get this to 30,000 customers?
And then their brains are thinking,
okay, I need to figure out partnerships
with these people who have 10,000 customers.
I need to figure out how I get people through a funnel
if I go out there and I spend this on cost per click
and with the conversion,
I will get their very analytical minded
(14:40):
because at the end of the day,
all of this conversation with business,
it all comes down to can you create value
that people can commercially recognize
for them to pay and for you to build a sustainable business?
So if it all comes down to that as a business,
then the commercial bits are really important.
It's how do you make money?
It's how do you make it sustainable?
It's how do you acquire customers cheaply?
(15:01):
And I will tell you here that being creative
can save you a lot on customer acquisition costs.
Do not underestimate how your creativity
can allow you capture lots of customers cheaply
in a way that allows you, gives you an edge up
in building a sustainable business.
As a founder, you're constantly selling.
You're selling to customers, you're selling to investors,
(15:22):
you're selling to early hires.
That commercial mindedness is just one of the things
that I found that the best founders that I've invested in
have really prioritized.
Yeah, 100%.
Coming back to some of our earlier episodes,
sometimes it does require doing things
that won't scale initially, but then an experimentation
and that will help unlock ways
(15:43):
you can figure out that distribution.
We do have a go to market episode as well.
So do tap into that, listen to that,
get some gems from that.
One other thing to think about is too much ego,
wanting to be the smartest person in the room.
Now this one is very tricky because I do believe
that ego is not necessarily a bad thing in and of itself,
but it's too much of it that becomes a problem.
(16:03):
Because if we think about it, sometimes you have something
to prove as a founder.
In fact, many founders oftentimes have egos
because it's personal.
It's something that they are trying to impress
their will into the world.
It's also very sensitive.
What I found with the best founders,
they know how to balance this.
They know how to balance that ambition,
that chip on your shoulder or feeling like,
you know what, I'm gonna show them.
(16:24):
I'm gonna show them that this thing will work.
With actually really understanding where your strengths
and your weaknesses lie,
I'm bringing really smart people around you.
And at the end of the day,
no matter how incredible you are as a founder,
if you're building a large high growth tech business,
your success is going to be underpinned by your ability
to get really smart, ambitious and motivated people on board
(16:48):
to collectively achieving that vision.
Yeah, I totally agree.
And I think that when you are building a startup,
it is a team effort on every single one of the episodes
that we've had today with our guests.
One of the key things that they always reiterate
is just how fundamental the team has been to their success
and ensuring that they incentivize the team,
(17:09):
how important culture has been.
And so you really should think about
how you can really foster and bring on board people
that are better than you as Maria said,
that is how you build a great company
because let's face it, without a great team,
your startup is literally nothing.
You cannot do all things.
You cannot, no matter how amazing you are,
just the work, yeah.
(17:30):
And Tim was actually quite honest about this
in his episode, in his first startup,
he was like, he realized that people were leaving
and he was like, okay, it's me, it's me, I'm the problem.
It's me.
So he was like, okay, I've been chasing
really high quality talents away
because of my perception, I need to change.
So that's another thing I think at the earliest stages,
as founders, as builders, that self-awareness is very key
(17:52):
to knowing that, okay, I might be passionate about this.
And there are times you have to put your feet down, right?
Like there are times that it's not so much
about trying to get everyone in the room,
but really being selective about those times
and making sure that you're getting
the value of the people in the room.
And like Yvonne said, no matter how awesome you are,
you need a team to be able to build a massive vision.
I think Sage said something in his episode
where he was like, you want to be told
(18:14):
that your idea is stupid.
And it's like, if to the extent that people can open up
and share things that are actually helpful
for you and the business, it absolutely helps.
Yeah, for sure.
Founders are humble enough to listen
and learn from their team, right?
Advisors, yes, you're gonna be getting advice
from all areas like left, right and center.
And ultimately it's down to you to make the decision, right?
(18:37):
But you have to remember
that leadership is really about empowerment.
It's not about just showing off how much you know.
It's really about the mission, why you're building
and wanting to grow with others on the journey
to build something that's truly scalable.
But ego is not always a bad thing.
Michelle's episode, Founder of Peanut,
where she said that she felt that she had something to prove.
(18:57):
She felt that she had that ego,
but she also did it with a team at the forefront.
Absolutely.
The next thing to think about
is not having a fundraising strategy.
Now, in this world today, in the way we think about startups
and especially the anatomy of startups,
it is you are starting off with an idea
(19:18):
or an early version of what a potential outcome could be.
And it needs to be funded somehow.
Even when you bootstrap,
you are funding with personal funding or revenue.
No business grows without some kind of funding.
Funding is the lifeblood of the company.
And fundraising is not just about capital.
It's also about the type of capital.
It's about the timing.
(19:39):
It's about the terms.
It's about the value add of that capital.
We need to be thinking holistically
about a fundraising strategy.
One mistake I've seen founders do is just go in
and not think about the strategy as well.
Definitely.
I think that for many first-time founders,
they really underestimate
what it really requires to fundraise.
Just being very specific in terms of the way
(20:00):
in which you do your outreach,
when you wanna meet investors.
In my personal opinion,
the best time to meet investors is when you're not raising.
And they have to be very strategic around it
because you don't wanna be speaking to investors
all the time,
because you wanna be heads down building.
However, you do wanna build those
and cultivate those relationships
before that point in which you're actually out raising
(20:22):
so that when you do go out to raise,
it's not like a drawn out period.
So one of the things that I personally really appreciate
is when a founder reaches out and says,
think about building this space.
I've seen you've invested in this company.
That's in an adjacent space.
I would love to get 15 minutes of your time
to run through your thoughts, perspectives,
any learnings that you could share.
(20:43):
I think that's a really smart way
of reaching out to investor,
getting on their radar,
building relationship with them
when you're not necessarily fundraising.
Absolutely.
And many of these fundraising announcements that you see,
they've happened like six months ago.
They're so lagging indicators.
And oftentimes when you see a successful fundraise,
(21:03):
the founders have been very deliberate.
It's just playing out.
They've done a lot of work
before they put in anything on that deck.
They've really thought about the story.
They've talked about the fit investors.
They've talked about the metrics.
They've talked about the narrative.
Fundraising is an art and a science.
And I think the best founders, especially now,
really know how to think about that.
(21:25):
And it underpins the ability to sell.
Because if you think about it as a high growth operator,
you are likelier to want to join a funded startup
than an unfunded startup.
Because you're like, if we have funding,
we have time to actually go find the market
and then there's more opportunity.
So I think fundraising and the ability to fundraise
and the ability to think strategically
about your fundraising growth story
(21:45):
is going to be very critical.
The other thing I like to say is that
sometimes you have to think of your startup as two products.
On one hand, you're solving a problem
for a potential customer.
So whatever product it is, say for example, Slack.
It's a software product.
But on the other hand,
you're actually pitching a product to investors.
You're pitching a financial product
that is potentially going to give the investors
(22:08):
multiple folds return later.
On the customer side, it's what can I get
in terms of value of using product.
But the investor side, it's completely different.
How much money can this startup make me
in the next five to 10 years?
Those pitches can be completely different.
Founders who tend to think of both
and really target the audience
in terms of what they're selling, how they position it.
(22:29):
So when you're speaking to an investor,
there's value that the product can create to the customer,
but you're in parallel painting the picture
about how this can be an incredibly
massive opportunity financially.
Like Yvonne said, speaking with people
long before you need to erase from them,
building that relationship,
and it doesn't necessarily have to be just VCs,
it's gonna be angels.
Put people in a bit of a newsletter when you start.
(22:51):
Start building those stories,
start making the dots become lines.
So that when you come, it doesn't seem like,
where did this come from?
Oh, this makes sense.
I knew you were building this.
Your background makes sense.
It's just logical that we invest.
So yeah, that's the one thing I'd add.
Yeah.
And other episodes where you would hear
how founders have gone about building relationships
with investors and when the best time to do outreach is.
(23:12):
So please do listen back.
And also just don't forget,
when you are thinking about fundraising,
it's not just money that you want,
but it's actually a partner that's gonna come along
on this journey with you for the next 10 years.
So choose wisely every time.
Now a bonus one that we wanted to share with you
is building a company with a co-founder
that you don't know well.
You'll be surprised actually one of the key reasons
(23:35):
why companies actually fail is because of co-founder splits.
When you are thinking about building a company with someone,
just be really intentional that you take time
and ensure that your missions and visions are aligned
and that you actually enjoy working together
and you can actually work together.
We've seen multiple occasions where companies have split,
where the founders have had a difference in opinion
(23:56):
or they just don't get along.
They can't work together.
It means that the company just doesn't go on
on some occasions, which is really unfortunate.
In Tim's episode, he actually shared how
he was very fortunate to have met his co-founder
at an event.
However, if he was building again,
then he would actually be really intentional
about working on a small project together with someone
(24:17):
before actually going out and building.
So if you do have the opportunity
to really like test that relationship,
then I would really suggest that simply because
on the journey of being a founder,
it's not an easy ride, it's a roller coaster.
You're gonna see people in all different scenarios
and you just wanna ensure that whoever you're building with
today is a person that you see yourself building with
(24:39):
over the next five or 10 years.
Absolutely, and it's hard to find that out, right?
Like even if you spend some time with them,
it's hard to find that out.
But it's quite unfortunate when that's why a company fails.
They might be having traction with customers.
They might have been onto something in the market,
but because the founders just can't get along
and make the relationship iterative
as opposed to this giant leap where you're like,
(25:01):
oh, we should just build a business.
Oh, that sounds great, but you don't know each other.
Start with a little bit of a project.
Try to get a sense of who they are,
what's important to them.
If this is something they want to do at this time,
it could also be timing.
You guys might be good together,
it might just not be a good time.
The other thing I would say is that sometimes
you might meet people who you've seen good on paper,
but good on paper doesn't mean actually like real life.
(25:23):
There are people who work well together, they're synergistic.
When they come together,
they're larger than the sum of its parts.
And then there are people who just don't have the chemistry.
They're good individually, but when they come together,
it just does not work out.
So really think about what complimentary skill sets
you're bringing, but then also do you gel as people?
Do you have aligned vision?
Do you have personalities that create value
(25:44):
when it comes together?
There are many high profile splits of founders
where people have strategic direction conflicts
and they're like, we're not seeing the world
the same way anymore.
And then there are people who,
even if one company doesn't work out
or they exit one company, they just go together
and start something else because they realize,
you know what, I know this person, we've worked together.
(26:05):
I think we can continue to work together.
100%, many, many examples from Jawbone to many others.
We round up, we've covered five, actually six areas
that we think are typical mistakes that we've seen
from our experience.
One of them is like selecting a poor fit problem
as we mentioned, you really wanna ensure that if possible,
you are associated with the problem you're solving,
(26:27):
whether that's from lived experience
or from your previous working experience,
you really wanna ensure that you have some sort
of unique insight in the market.
The other thing is just building a complex first product
without the customer.
Always put the customer first,
build with your customer's front of mind,
have design partners if you can.
If it's a consumer product, you wanna build with customers
(26:50):
every step of the way.
The other thing is just not focusing on distribution
and sales enough.
And we see, as we mentioned, we see this particularly
with first time founders.
You really wanna ensure that you figure out
go to market strategies.
And in the initial phases, this may mean things
that don't scale, but experiment, figure out what works
and have a clear path to distribution.
(27:12):
The other thing is like not having a clear
fundraising strategy, just ensuring that you really
understand how to go about fundraising,
the timing that requires, building those relationships
as early as you can, but also at the same time,
not spending too much time thinking about fundraising
before you've actually achieved any milestones
that are worth raising off the back of,
or just spending all the time speaking to investors
(27:35):
when really your customers should always come first.
And then building a company with a co-founder
that you don't know well.
If you can, go out there, experiment with them,
work on something small, like a small project,
and really just assess that relationship
before you go out and agree on something
that you wanna build when there may be cracks
later on down the line.
(27:56):
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(28:17):
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