SaaS Fundraising After Being Told She'd Never Raise

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host, Omer Khan, and this is a show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talk to Stephanie Lapierre, the founder and CEO of Tealbook, a supplier data platform that helps enterprise customers make better procurement decisions.
In 2014, Stephanie launched Tealbook initially as a service where she sold $5,000 memberships to suppliers who were selling to enterprise customers.
However, she realized this model couldn't scale when a larger customer wanted data on hundreds of thousands of suppliers rather than just a few hundred.
After years of bootstrapping tealbook from her living room while juggling the responsibilities of raising three children, Stephanie faced a pivotal moment.
She realized she needed to transform tealbook into a software platform.
But fundraising was really tough for Stephanie, mainly because investors were skeptical about her being a solo founder without a tech background.
And one investor bluntly told her, you'll never raise capital on your own.
You've got three kids, a funny accent, she's French Canadian, and you've never built a tech company.
Despite these challenges and harsh feedback, Stephanie rose to the occasion.
She knew she needed a strong team to get investors on board.
So she found a CTO who shared her vision for Tealbook and together they got to work.
By 2017, she successfully raised the funds she needed to grow the company.
Today, Tealbook is a seven figure SaaS business with over 100 enterprise customers.
The company has raised $72 million in funding and and grown to a team of 60 people.
In this episode, you'll learn how Stephanie's resilience and ability to adapt based on feedback helped her overcome challenges and scale tealbook.
How she persevered through investor rejections and ultimately secured funding by building a strong team and demonstrating traction, why tealbook made the decision to rebuild its platform, and how Stephanie navigated the tough challenges that came with that decision.
We also talk about how Stephanie leveraged thought leadership content on LinkedIn to establish credibility and gain more exposure for Tealbook in the early days.
And how Stephanie managed to balance her personal life and startup responsibilities while growing tealbook.
So I hope you enjoy it.
Stephanie, welcome to the show.

Stephany Lapierre (02:41.010)
Yeah, thank you for having me.

Omer (02:42.690)
My pleasure.
Do you have a favorite quote?
Something that inspires or motivates you that you can share with us?

Stephany Lapierre (02:48.810)
What's funny?
Because when I saw the question I was looking up, it just happened that I was talking to a few VCs of early stage companies and we talked about resiliency.
And so I know it's cliche, it is, you know, Steve Job.
But I like this where he says whenever the answer has been no for too many days in a row, I know I need to change something.
I'm convinced that about half of what separates successful entrepreneurs from the non successful ones is pure perseverance.
And I cannot, I cannot attest to this more because it's true.
It's so much about resiliency.

Omer (03:22.980)
Yeah, yeah, I love that too.
And I think that's a really good one with your story in particular.
We'll talk about this, you know, as we go.
But it applies not just to knows you get from other people, it's also when you're saying no or the voice inside in your head is saying no

Stephany Lapierre (03:41.150)
every Monday morning still today, every Monday morning it's like, what am I doing?

Omer (03:49.870)
So tell us about tealbook.
What does the product do?
Who's it for?
And what's the main problem you're helping to solve?

Stephany Lapierre (03:55.950)
Yeah, so our platform focuses on using technology, including AI to collect data on every B2B company in the world.
And so what we want to know is any supplier, so any business that sells products and services to an enterprise, we want to know as much as possible about them and we want to deliver to the enterprise quality information about who they do business with that's relevant typically to the buy side of a digital enterprise.
Simplifying it.
It's sort of where the zoom info to the buy side, all the attributes that we're looking for is to service the sort of the source to pay in the life cycle of a supplier.
Today, most of our customers, actually every company in the world, does really struggle with quality data because most of them, especially if they have in the thousands to tens of thousands to hundreds of thousands of suppliers globally, there's one.
Each supplier requires an enormous investment from sourcing them to onboarding them, to paying them, to maintaining their records.
And, and a lot of information does change and there's a lot of different needs across the organization.
So often you have multiple functions collecting the same information and that information is highly dependent on suppliers to maintain different portals.
And so what happens is that you have a lot of disparate solutions with incomplete, stale data that don't really connect.
And for companies who spend hundreds of millions to billions of dollars in their supply base to exchange products and services, but also maintain those relationship with talking about a significant investment and very little knowledge about who they do business with and no real opportunity to tap into that investment, who could be enormous levers for savings, for improving margin, for tapping into innovation, to hitting their ESG targets, et cetera.
And so that's the problem we're solving.
It's a big problem, it's a systemic problem in every single organization in the world.
And there's more and more disruption, as we're all aware, in supply chain.
There's more and more regulations that are asking for more transparency on sustainability, sustainability on risk, on cyber security and things like that.
And so that's what we're helping navigate for our customers in a way that's automated and a lot more intelligent and a lot more focused on business outcome and less of the doing of the data.

Omer (06:11.950)
Great.
That was a question I was going to ask you to help educate us on this whole business of procurement and suppliers, because if you're a small startup, it's not really an issue.
But when you're talking about the scale of some of these businesses that you serve, it's a completely different ball game.
So thank you for answering the question that I didn't ask.

Stephany Lapierre (06:35.210)
Yeah, it happens actually really fast because we have early stage customers who have a big dependency on suppliers.
So there's markets like biotech, for example, which a lot of their goods and services are outsourced and suddenly you're launching your first drug and you've got 2,000 suppliers globally, and so there's already quite a bit of disparity, and then you lack transparency and scale and enablement.
And for a startup, I'd say we're probably better positioned.
So if you're in a startup that has a marketplace or you're in the space where you need data, maybe you have built a niche solution or you're focused on a data problem that's maybe on esg, because there's a lot of those companies right now, or you're building workflow to enable supply chain procurement or any of those functions that required quality data for your customers to maximize the value of your product.
That's where we integrate our data into those systems so we can accelerate commercial value and then ensure that there's a better, faster experience for those customers that are using those products.

Omer (07:36.830)
Can you give us a sense of the size of the business?
Where are you in terms of revenue, number of customers, size of team?

Stephany Lapierre (07:42.910)
Yeah, so we're above 100 customers.
They're all large brand names.
For the majority, it's Fortune 1000 companies.
We're in the seven figures.
We have raised about 72 million in capital.
So we did a series B at the height of the market two years ago and the size of the team has changed quite a bit.
And so we've resized recently as we're releasing a brand new platform, focus on our future.
And it required quite a bit of change in the past year.
And so from a size perspective, we're about 60 people right now.

Omer (08:12.770)
And the business was founded 2014.

Stephany Lapierre (08:16.450)
Yeah, the first couple of years was bootstrapped from my living room.
I didn't raise capital until, until 2017.
And so depending you know how you count the first, the first years of Hustle was self funded and you know, everything is hard, but those years I kind of forgotten as pure survival.
But those were hard years and at the beginning I generated a million dollars in selling memberships to suppliers, which is a completely different business now.
But I was selling a subscription for about $5,000 and I needed five suppliers to pay $5,000 a month to be able to pay for my engineers.
And so that was the early days of, you know, able to self fund that.
So 2017 is when the company became more real.
We're able to get our first institutional round before that was self funded.
I did get an angel investor in about 2016 and so that gave me a little bit more time to then raise a proper round.

Omer (09:12.710)
Well, we love those early days here and those hustles and those struggles.
And so when like where did the idea for the initial business come from and what were you doing at the time?

Stephany Lapierre (09:23.380)
So I started this is not, this is my third company.
My second company was focused on helping initially was large companies to find innovation.
And so if you're sitting in a business and you have, you know, pretty competitive market and you want to differentiate your business, it's hard to find real innovation.
And so I came up with this concept, it was called Matchbook and helping businesses find innovation through typically it's third party providers who have innovated with other customers or solve similar problems or are coming up with ideas that could really differentiate a business.
That really quickly morphed into sourcing because my customers start recognizing a process that they had implemented within procurement and they really liked our process.
It was six weeks from requirements to outcome, which is speed light when you're thinking procurement processes.
My customers had asked if we could help bridge the gap between what procurement was trying to achieve and what the business needed, which is a pretty big gap with a lot of processes in between.
And so we started building strategic sourcing function for fairly established companies who had systems like SAP, Ariba, et cetera.
And then sort of fortunate at the time, a lot of my contacts went and start raising capital to launch their first commercial assets.
So at the beginning we're now in 16 sectors, but at the beginning was really focused on healthcare.
And so start helping biotech companies launch their first commercial asset and really building an outsourcing function that would be more transparent, that would be more scalable and enabling employees to make faster, better decisions.
And that's where I saw that every systems we would implement to automate payment, invoicing, contract sourcing, quality risk required quality data into that system to be implemented and then to actually deliver on the promise, value, value.
And achieving quality data was really hard.
And then it depended on employees, it depended on suppliers to come to portals.
And I saw that really quickly.
We're running into the same issues that my larger customers had where if you don't have quality data, how can you make better, faster decision?
I started seeing all these processes and all these roadblocks, achieving outcomes and it was really a data problem, not a software process or people to me just became, you know, if you had quality data that could power these systems and power workflow and decisions, you know, we could deliver significant outcome and maximize the investment made on this, this pretty big and growing supplier base.
It took me nine years.
Realistically, like I try to fight the idea for nine years I had a very successful consulting business, 40% margin.
You know, I reinvested in the business and grew it naturally and organically.
Never raised a dime for that company.
But this idea kept, you know, lurking and I tried to kill it in every possible way.
But every time I work with a new company, no matter the maturity level that they were at, they were struggling with data.
And then it became clear to me at some point, especially as cloud technology became more, you know, sort of massively adopted by our customers, they, I kept hearing very similar to the sales and marketing side.
You know, if you're going to get cloud based software, it will solve your data problem.
And I didn't see Salesforce in solve our data problem and made it easier to enter information in a cloud technology.
It didn't mean that the data was going to be good because it depended on humans and humans are not typically really good at updating data.
And then so I saw, I started seeing the parallels, you know, between what had happened in the sales and marketing side to what was really far behind on the buy side.
Seeing the adoption of cloud start seeing also the start of big data and machine learning was also very eye Opening that, we can maybe do this a bit differently and take a step to the cold start problem, which is how do you build a data set without having critical mass of inspiration in the beginning, with nine years of trying to kill the idea, to finally decide to do do something about it and turn my life upside down.

Omer (13:38.710)
Okay, so after nine years of resistance, you finally cave in and say, I'm going to go and pursue this idea.
How did you get started?
Did you kind of go out and do the kind of the lean startup thing and kind of validate this idea?
Or did you feel like the nine years of seeing this over and over again was the validation you needed?

Stephany Lapierre (14:03.190)
And yeah, it was definitely the validation I needed.
What I did not know is how to do it, because it's a very complex puzzle.
The problem that I saw is how do you uncouple this problem and why it's happening?
How do you build it?
The first version of tealbook, it was really deciding to create more of an interface for suppliers to come into a profile and populate their information.
The thesis was that if they came to one profile, we could distribute data across multiple customers.
And so that's what I sold the $5,000 membership for.
The reality is we didn't have enough customers to satisfy the demand.
And then when I started landing bigger customers, they asked for more data and then we didn't have the critical mass to offer more data.
So sort of the marketplace challenge anyway, so.
But when I decided I literally came back from working with a customer in San Francisco, it was a big company.
They sat across from Salesforce, LinkedIn, Facebook, SAP was across the street and they were facing this data problem.
And my consulting business took 16 weeks just to get baseline.
And sure, it was great for my consulting business, but I thought if this company that sits in San Francisco across all these other tech companies facing this problem, and I saw this to be like, we're talking about 100 million to billion dollar problem for one company.
This was a massive opportunity.
And so my husband took money from his own business and gave me a $50,000 check to get me started and ask a couple of things.
One, don't ever put our personal finances, you know, in jeopardy.
So make it work.
And if you run out of money, you're not putting the house, you know, on a lean.
And I would really like to stay married because, you know, I think, you know, probably being a bit wiser than I am, being 66 years older, sort of saw, you know, the possibility of me being really consumed by this business.
And so ask.
You know, it'd be great to stay married through this journey.
And so I always keep this in the back of my mind when he's asking me on a date for Valentine's Day and I have to leave my team for a team dinner to meet him.
You know, those are some of my priorities.

Omer (16:13.920)
Cool.
Okay, great.
So you've got, you've got the check and like this subscription that you were selling this membership.
How long, how long did you keep running with that and at what point did you pivot to kind of what Teal book sort of evolved into has become now?

Stephany Lapierre (16:33.850)
Yeah.
So I mean, it's kind of a fun story, but, well, at the time I don't know if I was, I was thinking it was this much fun.
But so I was selling these memberships and suppliers could put their credit card through the platform and I was giving these teal coins.
And so they would get 10 teal coins worth a hundred dollars.
And so when they got an opportunity that was fed through the platform because it was more sourcing at the time, they could apply these teal coins anyway.
But one day I landed this big company was a $60 billion market cap, clients with a big, in every way, chief procurement officer.
And he says, I, I like your LinkedIn thing but you know, let me know when you're ready for prime time.
And I was like, what do you mean, what does it mean being ready for prime time?
He says, well, I need, you know, I need 500,000 suppliers, not like hundreds or a thousand suppliers.
And so, you know, I didn't know how to get 500,000 suppliers because we had to sell this membership to each supplier.
So over a weekend we flipped the model upside down.
We made it free for suppliers that would get basically invited by this client.
And then I needed to find data on 500,000 suppliers.
And so I contacted, you know, so many different data source.
One kind of a funny story in full circle.
I went to Zoom Info in the early days and met a guy there that is now our president that I hired four months ago to run the day to day operations.
I went to Dun and Bradstreet, which I ended up buying D and B data and used my own money, I think it was $120,000 to get the DNB data in our platform so we could deliver on this client.
We flipped the model upside down.
And then shortly after I met our first CTO who had worked at Ariba for 10 years.
So he had the context of the business and then went back to school to Do a second master's in big data and machine learning.
And I'd worked at Google and Schenga and so we had all the pieces that we needed and when we hadn't yet ingested the D and B data and when he looked at it, it's like the data is not good enough for us to be able to use.
And so we ended up getting out of that contract and the decision was that we should build our own data.
We have the opportunity to build data that is better quality, get more of it more dynamic and better integrated into our customers processes.
And so that was a big decision for us to decide to basically build on GCP.
And we've completely rebuilt the platform in 2017.

Omer (19:00.340)
So wait, so you talk to this potential customer who tells you, tell me when you're ready for prime time.
You kind of basically flip things upside down over the weekend to try and get ready for prime time.
And then how long did it take after that to the point where you just said this, this D and B data doesn't work.
We need to be creating our own data.
Like I'm just trying to think of the timeline was that.

Stephany Lapierre (19:25.940)
Yeah, so I mean, he told me he was not ready for prime time on say a Thursday or Friday.
I managed to sign D and B over the weekend and Monday morning I flew to Boston, I met him in person and I had 1.8 million records.
And I told him, what's, you know, what's that for prime time?
He's like, oh, you rock star.
And so the reality in between, it was months before we even discovered that we couldn't get the data.
And so luckily those customers were moving really slowly.
So by the time we kind of revamped the platform at the time to enable this data to come in, then we needed capital.
I had six customers, including this big one.
And so I started fundraising.
And that's where I really stepped away from the business for a few months and met hundreds of investors trying to sell.
We had six clients, including this $60 billion market cap company.
And so that's when I met an investor that said, you need a team like Lone Ranger, you can't do this on your own.
And that's when I met the CTO that had the big data machine learning background.
And he's the one.
So it probably took about seven, eight, maybe even nine months before we were able to close a round of funding and then finally get him on board and then build a team that would built the second generation, basically which we now is our legacy platform.
But the concept of it was, blew my mind because at the time, you know, AI is pretty mainstream right now compared to what it was.
But I didn't know you could just, you know, built on, on.
We built on gcp, start leveraging some of their machine learning models, hired some data scientists and start tackling this problem ourself, which was pretty, like, it was magic, like incredible.
Lots of work, right?
Lots.
Like now it's, you know, the technology's advanced so much.
But back then it was pretty, pretty amazing that we could do this.
Now no one understood it, right?
So the problem we had now is like, explain this to a customer.
We go on the web and we collect information and we put in the cloud and we match it with your vendor master.
That was really hard to explain to investors as well because you're not your SaaS, but you're really the values in the data and then the data moat, it's not traditional SaaS.
And so finding who we are and what's our North Star and how do we build a moat around our technology was not as simple for us to understand or to be able to explain to investors.
And the big click, I think for investors is when one of our investor Seed plus round, that's Tim Shigl at Refinery Ventures, said, can you find an analogy to your business that people could understand?
And that's really when the zoom info analogy came into play.
I had an executive at the time that sort of look at the markets, like, I think that's the closest thing.
It's not perfect, but it's pretty close.
If you think of, you know, zoom info being focused on enriching customer data and then be able to integrate that customer data into salesforce so that sales and marketing can deliver better, faster outcome.
It was a very synergistic analogy that investors understood.
Luckily for us, ZoomInfo went public shortly after.
And so when we went to the second round and ZoomInfo did very well in the public market, so that sort of got people pretty excited.

Omer (22:41.200)
So let's talk about the fundraising.
This is your third company at the time that you're building, you have spent many years in this space.
You understand procurement, you have spent several years bootstrapping and, you know, getting the foundation of this business.
You've signed some deals and some customers and, you know, so everything looks great.
You've done a lot of the hard work.
You know, in terms of like getting that initial traction, it seems like fundraising should have been fairly easy.
Was it?

Stephany Lapierre (23:24.300)
No, it wasn't.
Maybe something for founders, you know, you Always think like, oh, once I get that check, or once I get that customer, once I get that employee, the world will be amazing.
There's always.
It always comes with, you know, another baggage.
No, fundraising was not easy.
I mean, it got easier as we, you know, build momentum and got more customers.
So series A and B were actually both preemptive term sheets.
So completely different story.
But in the early days, yeah, it was definitely challenging.
So I'd say the first one was not a real representation of reality.
And we didn't talk about this, but my first.
First angel check I got when I was watching one of my daughters play soccer, and I had a mom next to me who asked me.
She was, what do you do?
You're always running around in your high heels and with your babies.
And so I told her what I was doing, and I said, well, I'm going to be traveling even more because I'm starting to fundraise.
And she goes, well, what's your business?
And we start chatting, and she goes, I'd love to put money in.
And so she ended up giving me a million dollars.
That doesn't happen in reality.
But what I would have to say is that what she saw me is hustle consistently.
And this is was someone who had wealth, who needed to invest.
And it was either she was going to go on angel, you know, websites and look for deals, or she could invest in someone that she had seen working hard at building a business.
And so once she understood the business, she got pretty excited about what I was doing.
And so I think, you know, just make sure that you leverage your network.
That was really important for my angel rounds initially as well.
But, you know, when I look for institutional capital, I had delusion because of the first round that it was going to be easy, and it really wasn't.
And it took me to speak to hundreds of investors for one to be really honest.
And I owe him.
If he ever listens, he knows, but I owe him.
Him.
He didn't invest, but it was, you know, is honesty, which at the time took me aback.
But he's the one who said, you know, you lone ranger, you'll never be able to raise capital on your own.
Like, you can't build this business on your own.
Like, you know, you got three kids, you get a funny accent.
I'm French Canadian.
You've never built a tech company.
You have no pedigree.
You get no tech background.
Like, who are you?
I kind of entertained by my passion for solving this massive problem.
And so.
But at the time, I said, Well, I need capital to hire the team.
He's like, you're not going to be able to raise capital without the team.
And I remember leaving this meeting, first of all, so defeated.
Like, he highlighted all my problems, like, all my gaps, I should say my problems, all my gaps.
And I thought, how can I hire people?
Like, what he was asking is, like, you need to build a team.
I was like, how can I build a team if I have no money to build a team?
And I had, like, three months of Runway, maybe even less.
And so.
But it did change my mindset on how I had to think about myself.
And my was not my gender, my accent, or my lack of tech experience.
It was my risk profile.
Me on my own.
Like, what happens if my kids got sick or, you know, or whatever.
My risk profile was too big for someone to write, you know, a multimillion dollar check.
And so that's when I start looking for, you know, at the time, I wasn't sure if it was co, founder or executives, but I had built already two, three years.
And so I was more focused on finding executives where I could do give, you know, significant options but as employees and bring in the company.
And I was, you know, the stars align.
There's a lot of magic dust that follows you when you build a company.
And so that was one moment where someone said, hey, I, I, I know someone that may be interested.
He just exited from a company.
Maybe he'll come with money and a team.
And I think he's got experience in your space.
And that's when I met Jeff, our first cto.
And then he did come with the CEO of the company that exited, which I then turned into our coo, and they both put money in.
And then we went back to the investors that had already shown interest, say, hey, we now have a team.
They put money in the round.
You know, they have a lot of experience building this type of company in a lot of context in our space.
And so that got us the first institutional round.
So, again, it was not all these other things.
It was just, how do I look at myself in the mirror from the lens of an investor?
And how can I reduce my risk profile to increase my chance of raising capital?
Because the business needed that.

Omer (27:46.430)
What a great story.
It's like, you know, having a conversation like that is almost like, thanks for the pep talk.
I'm, like, totally depressed now, right?

Stephany Lapierre (27:56.310)
But I remember this guy that, you know, was in his maybe his late 20s or early 30s.
He's like, you know, Steph, you just have to Be cocky.
When you're talking to investors, like you're looking at it with his baseball hat and this young, you know, cocky look.
And I was like, well, I'm, you know, I'm older than you.
I'm a woman, a mom of three kids.
Like, how.
But then what I need to do is reflect on what does that mean for me.
It's not the cockiness, it was the confidence.
And it shifted from which I hear a lot from early founders.
Well, I need money to grow my business.
Well, investors don't care about that.
They care about making money.
Like, if they take a bet on you and why would they invest on you versus invest in another company?
They need to believe, they need to have the confidence.
And most importantly, they don't want to regret.
They don't want to regret down the line saying, like, I had the opportunity to invest in that company and I didn't.
And so how do you turn that confidence so that they feel like they're going to miss out?
And that's when I did the switch to in fundraising.
I changed my narrative and it became really powerful.
And, you know, recently, ish, I was at a dinner and an investor's like, oh, this is, you know, introduce me.
She goes, she raises like a man.
Like, I don't know if it's a compliment or an insult, but what she meant is I had the confidence, right, to be able to raise capital.
And that confidence came because one, I believe in my business.
But I changed my narrative.
And so it became, you know, why would I want you as an investor?
Like, what strategic value or, you know, why giving you the opportunity when I have, you know, other people that want to put a check in.
And so suddenly it's sort of.
And then, you know, what I've done?
I think, wow, that I could have done better in the early days is I created one the investment thesis, like, why this problem?
What's happening in the market that we can attach ourselves to?
Something that's growing really fast for us was sort of the BI market that was growing really quickly, the adoption of cloud, the growing source to pay software market.
Why us?
All the years of experience, as you pointed out, then the deep understanding of the space and then the analogy, it's not the headline, but to say we're the zoom info to the buy side.
That became the investment thesis that made it easier for investors to understand and sort of get excited about and how big our TAM was.
And then the other thing that I did is put milestones that were achievable that I knew we could achieve, but they were impressive enough.
And I put four or five milestones we want to achieve, say next quarter, this quarter.
And then I would let investors know what we set out to do.
And then every time we reach that milestone, I would send a note, hey, we got, you know, we got covered by an analyst.
We closed this partnership, we closed this, these two customers, I told you we're going to close.
So every time it's kind of a boom, you know, and then they get excited and so then you create a little bit of excitement around your company and all they care about, well, you have what it takes.
Because it's so hard.
Well, you have what it takes to stick through it, right, and deliver on what you say you're going to deliver.
And that's the most important thing for investors.

Omer (31:00.040)
So I got to ask, where does that, where do you find that next level of confidence?
Like, you go in, you kind of heard this lesson and you start to think about, okay, what does this mean to me, what do I need to do differently?
How do I reduce this risk profile, all that stuff.
But you know, we are who we are and to suddenly, to change like that and to kind of bring in this kind of Newfoundland confidence is, it's like, how did you do that?

Stephany Lapierre (31:31.730)
Well, if you're going to be a founder of a successful company, one, you have to be incredibly self aware of who you are.
You've got to be able to listen, right?
Feedback is super important in every aspect of your business and you can be so firm on your belief that you, you're not willing to listen to feedback and then you, you have to reflect on the feedback based on your situation.
In these two cases, I had to apply it to my situation and you got to find it, like, if your company needs money, it's that or death.
So better find the confidence.
Nobody's going to invest in a company where the founder is not 100% confident and doesn't have the conviction.
Now what I've said to early investors, I said, don't put your life saving in my company because we have 1% chance of making this a success.
But what I'll tell you is if we win, we win really big.
And I will do whatever it takes to make this company a success.
And so, and as soon as I had an angel investor kept texting me and calling me, how's it going?
And he had put $100,000 in the company and I was like, hey, I'm going to give you your check back.
Like, what do you mean?
I was like, I can't.
Like, I can't be answering your text.
And if you're nervous about your $100,000, which I totally understand, it's a lot of money, but if that $100,000, you're not willing to lose it, I rather give it back to you.
I don't want to have that sense of responsibility now.
Obviously, the accountability to my investors have grown and, you know, and it was really important to do right on my early investors.
And so I did secondary and gave a lot of my early investor a chance, at least cash some out, even double or triple their investment.
And my purpose with that is that if I were ever to knock on their door again, that, you know, I had made them successful, no matter the outcome.
And so I did that for them.
And then, you know, and then I have, you know, very happy investors who still have an upside in the company and are still, you know, supportive and cheering on.
But you have to find it.
There's, there's just no.
Your company needs money, you need money, and so go get it.

Omer (33:30.570)
Yeah, it's, it's, it's funny what, what we can find in those situations where you realize it's like, you know, if you don't do something, you know, the company's going to die or whatever.
Right.
And.

Stephany Lapierre (33:44.490)
And you have to be optimistic.
Like, I, I had someone recently.
She goes, I have a hard time.
She worked for me.
She goes, I have a really hard time balancing your optimism.
This was like a total fair comment.
I was like, holy.
If I was not this optimistic, there'd be no company.
Right?
You have to be through the good and the bad.
You have to, you know, you have to have conviction.
And there's always a way.
You just have to.
You have to find the way.
And sometimes it's a hard set on reality, on where you're at and the changes that you need to make.
And some of those changes are really, really hard, especially when it comes to people, like people, it becomes emotional.
Change is hard.
And so.
But, you know, you have to be adaptable as well to those changes.
And again, sometimes it's stepping away from the business and see what does the business really need.
If I was an investor in that business, what would I tell my founder CEO that they would need to do to get things back on track or what, where they should be focusing their effort or how they should be balancing themselves?
You know, sometimes I sort of take that lens because I think it's important to step outside of my own head and, you know, give myself Advice?

Omer (34:48.680)
Yeah, let's talk about some of those early customers.
And I know that you're doing a lot of thought leadership as a way to connect with these customers, but, you know, we've just talked about everything that was going on.
You're trying to build this company as a solo founder.
You don't have a tech background.
You're trying to raise money.
You've got your three girls who were pretty young at the time.
And then someone said to you, hey, you should start writing on LinkedIn because you have a lot of time to do this, right?
Can you tell us about that?
What happened?

Stephany Lapierre (35:26.340)
Yeah, no, that's exactly it.
A friend of mine in PR said you should start writing a blog.
And it doesn't matter the frequency.
What matters is the consistency.
If you choose once a month, write once a month consistently.
If you choose once a week, do that once a week.
So I picked once a week.
And as a, you know, English is my second language.
It's better now than it was back then, but it was still pretty daunting to write in a second language and once a week.
But what it did is it forced me to pay attention to things I want to write about, read more content I could repurpose.
And I became, back then, I was traveling a lot more, and I remember on tarmac, I would write, you know, it could be I met someone and it, you know, the opportunity to put your phone down and have a conversation with your neighbor, like, stuff, right?
But it.
It forced me to write and that create more of a presence, and it started building more of a sense of community, I think, within the function, which is procurement.
I also spent hours and hours and hours connecting with people on LinkedIn back in the days when, you know, it was not as crowded.
So that gave me a bit of an edge.
And I would send notes to chief procurement officers saying, hey, I'm, you know, I'm thinking about building this company, or I'm in the stage of building this company.
Solve this problem.
Is it something that you're seeing in your business?
Would you mind spending half an hour of your time to connect, just to better understand, you know, what challenges you're facing, making sure that.
And so.
And the worst that people are going to do is not get back to you or say no, which rarely actually happened.
Like, people are pretty open to sharing their insight.
And especially in procurement, you're in a function that doesn't get a lot of recognition and time.
And so someone's asking for your opinion and your views on the world.
And so I Was really fortunate.
People were very generous with their time.
I think it would be harder now just because it's so crowded and there's a lot of, you know, optionality in tech and a lot of startups.
But back then there's only, you know, five startups, I think, that were focused in the procurement space.
And so that was pretty novel and exciting.
But that all contributed to thought leadership and building a fellowship and then taking any speaking opportunities that it's a podcast, that it's an opportunity to present on stage.
And I bartered, I bartered so much in the early days to get an opportunity to speak on stages.
Now I can't.
Do you raise capital now they want money from you.
But in the early days, being scrappy and finding topics that conferences were really keen and AI was very new, data was very new.
Being a tech founder was very new in their space.
And so it gave me a bit of a, you know, an edge to be able to position myself to do speaking engagement and got more comfortable.
I was not comfortable doing podcasts or, you know, being on camera and, you know, go live.
I was like, that was, that was hard for me, especially being my second language.
But I got better and the more I did it, the more comfortable I became being on stage.
And so, yeah, I mean, I've done now countless speaking engagement and I find a lot of energy in them now.
But, you know, we're talking about eight, nine years of building that thought leadership.

Omer (38:31.360)
You mentioned the tech platform earlier and how you, a couple of years ago, you set out on this reset and to kind of rebuild the platform.
What happened there?
What were some of the problems that the business was starting to experience that led you to do this in terms of, I mean, it sounds like a pretty dramatic kind of thing to do.

Stephany Lapierre (38:59.640)
Well, so that one was actually fairly easy.
We just switched, we just rebuild the database, rebuild the application, and our customers just switch on to the new one lately.
And what we did, you know, you're scrappy in the early days.
You make sacrifices.
We used older tech.
We built with.
We had a lot of co op students in the early version of tealbook, I think we had like six engineers and nine co op students.
Nothing was documented.
But what we're trying to get is an mvp and we didn't know the use case we're going to go after.
So once we got to learn the use cases, what data our customers need, the expectation on quality of our data.
And so we build a lot of stuff in the early days that became irrelevant.
So we had Collected quite a bit of technical debt.
A lot of it was was application software based because our customers only understood software at the time.
And the big problem for us is in the second generation we grew 350% in 2021 and a lot of that was because of COVID And when we started getting a lot of vendor masters from customers that were closing really fast and then we were getting customers to want to refresh their data for reporting purposes faster and then we're trying to refresh large data set that we had ingested.
The whole thing was unscalable and it became almost a company killer because we had no real processes around it.
And so it's like the company outgrew the tech and then we had to take a hard look at the technology and take all the learnings, take the advancement in technology.
We now had capital to hire different type of talent and so we decided to replatform a couple of years ago.
So the first replatform was easier than the second one.
The second one, you know, there's a lot of complexity in what we built and you know, it's definitely something that in hindsight I think we could have upgraded without having to do a full rebuild.
I think that would have been an easier, faster path.
Super happy now that we are sort of, we've delivered a new platform and it's performing and now we're building on it.
But the, you know, the challenges and the stress on the company and the change management required to bring this new platform to market was, you know, I completely underestimate.
So from an early stage perspective, I don't know there's a other way around it.
When you're scrappy and you've got, you know, not a ton of capital to build a tech, especially if it's a complex tech, I think it's easier now because there's so many things you can just grab and implement versus us.
We built ML models, you know, we don't really do that anymore.
So it's easier to build better tech faster than it was back in the days for sure.
And you know, I think if someone suggests you to completely replatform, if there's any other alternative, any ways to, you know, upgrade it over time or in parts of it, I strongly suggest that you do that.
It would avoid a lot of pains.
And since then, when I've told another founder we've replatformed, it usually follows with it.
Oof.
How did that go?
It's usually, yeah, I wish someone had told me to not do that Anyway, so yeah, there's reasons, obviously you do it for us.
It was scale.
We needed to operate more efficiently.
We need to scale.
We need to ingest a lot more data faster, more automated.
We need to give our customers more confidence and transparency in the quality of our data.
We need more flexibility in how our data was going to be distributed.
So there's a lot of reasons we did it.
But, you know, I think it's.
Yeah.

Omer (42:31.970)
Oof.
Yeah.
All right, we should wrap up.
So I'm going to get into the lightning round.
I've got seven quick fire questions for you, just for you to try and answer them as quickly as you can.
What's one of the best pieces of business advice you've received?

Stephany Lapierre (42:49.890)
I don't know if that's a good advice, but I took it.
So don't build a plan.
The plan will come with the business.

Omer (42:54.770)
What book would you recommend to our audience and why?

Stephany Lapierre (42:58.340)
The Four Agreements.
It's a little, tiny little book.
It puts things in perspective.
I try to read it once a year if I can, to just recenter myself on things that are really important matters.

Omer (43:09.060)
Love that book.
I think I've got my bookshelf there somewhere.
Just like five feet away.
What's one attribute or characteristic in your mind of a successful founder?

Stephany Lapierre (43:18.260)
Resilience.

Omer (43:19.620)
What's your favorite personal productivity tool or habit?

Stephany Lapierre (43:22.900)
I love ChatGPT.
I use it for my travels.
I use it for writing content.
I. I'm a big fan.

Omer (43:30.640)
What's a new or crazy business idea you'd love to pursue if you had the time?

Stephany Lapierre (43:34.240)
Oh, I would probably do a teal book for saving parents having to register their kids to the thousands of activities and camps and school.
I will not solve this problem.
But that's my biggest pet peeve.
When you have three kids with different interests, the amount of time you have to redo the same things in different forms and none of it connects.
Oh, AI in there would be fantastic.

Omer (43:58.570)
It's funny you say that my.
My daughter and my wife were arguing yesterday because she was saying, you need to register me for softball.
And my wife was saying, I can never log into that thing.
And like, you know, it.
It's like, yeah, it's.
It happens like every.
Every few weeks or months.

Stephany Lapierre (44:15.370)
Like three camps times three kids, times like nine different forms.
I'm telling you, like, that problem someone needs to solve.
I will not solve this problem.
But if someone wants to sol buy that product.

Omer (44:28.790)
What's an interesting or fun fact about you that most people don't know?

Stephany Lapierre (44:33.270)
I'm a photographer.
I Don't know if that's fun fact.
I love photography.
I see the world in pictures.
I take a lot of pictures.
I have, I don't know, maybe a million pictures on my phone, most of my kids.

Omer (44:44.550)
And finally, what's one of your most important passions outside of your work?

Stephany Lapierre (44:47.910)
My family and I'm a big skier and so my whole family.
Yeah, we ski a lot.
I've grown up skiing.
I was a ski instructor in Whistler back a million years ago.
And it's definitely a priority for our kids.

Omer (45:01.950)
Love it.
Stephanie, thank you so much for joining me.
It's been a pleasure.
Just kind of.
I know it's always hard to kind of unpack a 10 year journey and kind of, you know, have all the answers.
I appreciate you kind of taking us through that.
If people want to find out about Teal Book, they can go to tealbook.com and if folks want to get in touch with you, what's the best way for them to do that?

Stephany Lapierre (45:25.310)
Yeah, I mean, you can always email me.
It's Stephanie with a yieldbook.com.
i'm on LinkedIn.
I'm very active, as you heard today, so just be careful.
If you follow me, make sure you care about supply chain data, digital transformation, procurement.
But you can find me on LinkedIn.
I'm always happy to respond if you want to exchange ideas.
Yeah, that's probably the best way to get in touch.

Omer (45:45.670)
Awesome.
Thank you.
It's been a pleasure and I wish you and the team the best of success.

Stephany Lapierre (45:49.860)
Yeah.
Thank you so much for having me.

Omer (45:51.700)
My pleasure.
Cheers.