Narrative Shift: How Stephany Lapierre Raised Millions on her CEO Journey

Tune into my conversation with Stephany Lapierre, the founder and CEO of Tealbook, as she recounts her journey from a background in consulting to becoming a trailblazing female founder in the tech industry.

Delve into the Transcripts for Key Takeaways from this Episode

Mark MacLeod:
In this episode, I sit down with Stephany Lapierre, founder and CEO of Tealbook. Tealbook began as a services business, leveraging Stephany’s deep domain expertise, but she turned it into a software business nine years ago.

Stephany is a solo founder and it’s hard enough doing a business with co-founders. She’s doing it all by herself. We go deep into that journey, how she went from services to product, how she grew herself as a CEO, the impact of COVID re-platforming, how she built her leadership team, the challenges of being a female founder in a male-dominated environment, and many, many more topics.

Stephany, welcome to The Startup CEO Show. It’s a true pleasure to have you here. How are you today?

Stephany Lapierre:
I’m good. I am honored to be speaking with you today.

Mark MacLeod:
Sweet. We were just talking before we started about how impressive your wall is. So for anyone who’s watching on YouTube, there’s some wallpaper inspiration there. Would love to start with the origin story, and how it is that you came up with the idea for Tealbook, especially since you don’t come from a standard kind of founder background. How did you come up with this company?

Stephany Lapierre:
I started a consulting practice 16 years ago and the concept of the consulting business was to help large enterprise people within large enterprises that are looking for innovation. And so the idea was to help match the business requirements of the organization with some suppliers that either solved the problem for other clients, because often problems are not that unique, or come up with an innovative way to differentiate or address a challenge.

So that company was called Matchbook and it started that way. We built a process that would make it easy on the client side to identify suppliers that would bring innovation, which had a lot of parallels with procurement and the shift of procurement, moving from a cost-saving function to a more value-add function with a focus on how do we deliver more value to our stakeholders within the company.

And so it’s sort of the parallels were being made by our clients liking the process and asking my consulting firm to help them shape what the strategic sourcing function was going to look like. And so for a couple of years, I had the opportunity to work with really large enterprise customers who had a lot of procurement systems like SAP, Ariba, and others.

And what I kept noticing was that information about suppliers was incredibly difficult to access across businesses, even a lot of decentralized organizations. So different functions, different organizations, and the management was trying to harness the information on their suppliers and it was very difficult, especially when we’re talking about having ten or 50 or 100,000 suppliers globally. It was very disparate.

Companies were trying to reduce the size of their supplier base, often by this lofty goal of 50%, but they didn’t know much, if anything at all, about the majority of their suppliers. So in my view, how do you optimize this investment on the suppliers that are already in contract and doing business if you don’t know anything about them? It was like, imagine a world where we’re running revenue teams with no data on our customers or we’re prospecting customers. It was very similar.

And I saw the day-to-day struggle of stakeholders trying to access basic things like who do we use for X, Y, and Z, and what are the contract terms and what alternative suppliers are in our market that could bring more innovation or could be more competitive. So I saw it from a large company lens and then a lot of my customers shifted to go to smaller companies. And at the time it was very specific to pharmaceutical and biotech. And so during the biotech boom, in 2009/2010, my customers were building supply chains for the first time.

So they’re raising large rounds of capital. They had six, you know, maybe 12 to 18 months to bring a product to market and they needed hundreds if not thousands of suppliers. And so, initiate started very much like Steph, we need X, Y, and Z. So we would help them find those suppliers to suddenly seem like, hey, there’s a very distinct lifecycle that every company is facing. Is there a way to build a consulting firm that would help them build a procurement function out of the gate that would be more scalable, transparent, and enabling for the organization to be able to build a sustainable, scalable, resilient supply chain?

And then I started seeing very quickly with the lens of if we could start this from a clean slate, could we make it better? And very quickly realized that as we started introducing and implementing systems to try to automate sourcing, contract payment, etc, we were creating a lot of disparity. And very quickly we lost sight of the information that we needed. And suddenly you lack transparency. It was unscalable.

You sort of patch it with manual processes, a lot of swivel chairs between these systems, systems, and you lose that macro view of how to optimize investment. So it was a nine-year process of trying to kill this idea that this is a data problem, it’s not a software people or process problem.

If we could find a way to sort of harness this data and make it more consumable, deliver better insight, or even distribute better quality information on suppliers across all these systems and these functions that need it to deliver business outcomes, I think this could be a pretty big idea. And we saw over time that this was not just a reality for pharma and biotech. This was systemic across every single organization, no matter the maturity, no matter the stage of their digital transformation or the sector.

So, I saw it as a really big problem to solve. And so I’ve been on this journey now for roughly eight years to try to solve it. And it is a really hard problem to solve. That’s why no one had solved it before.

Mark MacLeod:
Wow, what a journey. It’s funny, I’m amazed that your clients would be big enough to be considered enterprises and not have this kind of infrastructure in place. Kind of blows my mind. But then again, I don’t come from the enterprise world, so I’m blissfully ignorant.

Were you reluctant to move on to this next phase? Like, did you sort of reluctantly say, oh, shoot, I guess I better create a software company, or actually, you were kind of enthusiastic about it?

Stephany Lapierre:
I fought it. I fought it having three kids. And at the time, before I started putting the idea together, I had two daughters, and then got pregnant with Sophie, my third daughter, while I was ideating on the process.

But for every customer I work with, I thought if they had this thing, it would solve so many of their problems. It would enable all these use cases that they’re trying to solve through workflows, you know, portals, and so I did fight it. I found every way to kill the idea. My business, you know, was generating 40% margin, but so profitable from basically the first year.

I never borrowed money and never raised capital. And so it was pretty daunting to start a tech company. And I knew for this to fly, it would need to attain a certain critical mass, which would require capital and a lot of expertise to bring it to life. So, I spent nine years trying to kill the concept.

Mark MacLeod:
Your company is a cockroach, unkillable. I like that.

Stephany Lapierre:
Yeah, sort of. I’d probably save the same analogy for my resilience.

Mark MacLeod:
Yeah, exactly. Those are 100% correlated.

And so TealBook is your fourth startup after your three children. That’s pretty wild.

Stephany Lapierre:
Was my third startup from a real business sense. My first business was when I was 18. I sold that and then took the proceed to be a ski bomb for a year in Whistler and then started Matchbook 2006. It was about 2006, and then TealBook came to life in about 2015.

Mark MacLeod:
Wow, that’s great. So, you know, back when I was a VC, a long time ago, in the dark ages, we shy-ed away from solo founder businesses because it’s just so hard building a startup and especially taking it to where it can generate a return that moves the needle for a venture fund. It’s hard enough to do with partners, and you did it by yourself. We’d love to know how that journey has been for you, especially since you had domain knowledge, but didn’t, you know, didn’t come from a software product management background. Just walk us through that. And if you had a do-over, would you get a co-founder? I’d love to learn more.

Stephany Lapierre:
Yeah, I would never do this by myself again. It’s lonely, and the tough decisions rely on me. But I heard the double-edged swords, you get partners, and things don’t work out. Not everybody can scale with the business. At some point, you have to make these really difficult changes. It’s easier in some ways if people are employees, even though they’re executives in the company, to make those types of changes.

And I’ve had to change my leadership team several times. So who knows, maybe the co-founder that would have been at the beginning would have not been, you know, the right CTO, for example.

So I do count my blessings, although, you know, being a single founder is really hard. Luckily, I’m passionate about solving the problem and the market has continued to validate that this is something that needs to be solved. It’s been accelerated with COVID because most enterprises that said, oh, I have good spend visibility or I have a good handle on my spend data, suddenly something that big happens.

Spend is relevant, but it’s not that particularly as useful as understanding where you have risk in your supply chain and where you need to find alternative suppliers, or then suddenly you get black lives matter. Now you need to know who your suppliers are, whether they’re women-owned, veteran-owned, or small business-owned, and suddenly you get carbon emissions so that you need to stay, that the requirements have continued to compound in a way that it’s impossible for enterprise today without having a solid data foundation to realize and be able to satisfy all these different regulations and requirements and all the disruption that will continue to happen.

So, fortunate that the world of technology with AI, BigData, and then also all the other factors that contributed to raising awareness to the importance of having good data. It all starts with good data.

When you ask the enterprise, so how do you do this? Well, that’s the hard bit. Well, if the hard part is starting with good data and that’s not possible to achieve, then what are you doing? You’re building an architecture with a lot of software and processes, you’re not solving the data problem.

So, yeah, really fortunate that all the pieces, and that’s what’s kept me so motivated and excited about solving the problem is because the market has started to see it. In the early days, no one understood what I was trying to do, investors, customers, or even recruiting people. It was challenging because no one saw the problem the way I could see it at the time.

Mark MacLeod:
Yeah, I believe that. So you brought up COVID, and I was thinking before we chatted, that when I think of really sexy kind of vertical markets or sectors, supply chain is not top of the list for me, but supply chain was on everyone’s lips during COVID because our supply chains were disrupted massively. This brings up what I think is the most important factor in the outcome of a startup, which is timing. Was COVID just a big accelerant for your business?

Stephany Lapierre:
It was in the way that it gave a lot of tangible use cases for data. So examples where we helped the Burke Brothers identify net new suppliers to be able to produce 100,000 PPE masks within a couple of weeks. And they were producing that every day. They could have not been accelerated in the way that they could because of our platform.

We set up the UK government with a database of 60,000 manufacturers of PPEs with contact information, with ISO certification, with years founded. It gave software companies more awareness of the need to be able to partner and integrate our data.

What I would say is that in some ways we were in the early days, we were quite underfunded when we started to develop the tech. And so the acceleration, we grew 350% that year, or MdR went from 90 to 160, which gave us amazing metrics to raise series A and series B. But what we didn’t anticipate was that tech was not ready for it.

And so from a scalability perspective, we ended up running into a lot of really big issues of how we were loading vendor masters of our customers who needed data faster, how we could refresh our pipeline so that we could add more data and make sure that our data kept up to date and we didn’t have provenance. So we had challenges around overriding some of the data that we already had on our platform. So it created a lot of issues for us, which we ended up sort of patching with people and processes and then deciding to rebuild the technology.

And so, in hindsight, if we had the tech that we, you know, we’ve released recently and we’re iterating on it, that has a lot more sophistication, a lot more scalability, and efficiency in the way that we build the architecture, we would have been much better prepared to take full advantage of the growth that we experience. We kind of had almost a two-year period of growth, and then we had to reset to get the tech to where we needed to be.

The good news is the problem is not going away, and no one’s solving it yet. But we also know that technologies advance at a pace that some components of the use cases that we used to focus on have become, you know, much more commoditized. And so staying on, you know, staying ahead of that is important for us.

Mark MacLeod:
That’s fascinating. In my last operating role at FreshBooks, we went through a re-platforming. The company was in the teens. I was on the original platform, and Mike, the CEO at the time, likened re-platforming to changing the engines of a plane while it’s flying. Was it that kind of daunting for you, or it wasn’t too bad?

Stephany Lapierre:
If I knew what I know now, I would have probably not re-platformed. Frankly, I would have just upgraded the components of it over time. It was easy to understand the rationale for why we should re-platform. The business case for doing it seemed more obvious. And then the timeline that we had set to do it was also pretty clear. I think the execution of it was more challenging, and I think the team that we had brought in was trying to solve all the problems of the old platform and bring a platform to market that was sort of, you know, more complex, more sophisticated, but without having customers touching the data, and that was a big mistake.

You know, the first platform we built and very modular, and so we were able to expose data and refine and grow with it. As a second generation, we ended up with this very monolithic technology that we had to then decouple again.

So, yeah, it’s more on the execution of it that we ended up facing some challenges. But if I knew what I know now, I would have probably taken a different path. And so, now I talk to founders who say, oh, you’ve re-platformed. How was that? And I was like, no one said that to me, you know, when we were considering re-platforming. You know, maybe I didn’t hear it. I thought we would be different, which is a great lesson learned from any of the other founders who may be listening to this right now. Look at your options carefully.

In a way, I remember at some point in the early days, we thought, let’s give this to a separate team, and we know we’re going to throw away one of the two architectures, but it would have been less costly and it would have been more effective to do it this way because we could have brought something to market much faster.

And so, yeah, we’re fortunate. Our old technology, our legacy technology still works. We have hundreds of customers. We’re able to satisfy their use cases. But this new platform solves so many other use cases at a scale and efficiency that will be unmatched when we’re ready to roll it out in primetime. We have customers on it now, but we’re being very careful before releasing it until we’ve nailed the product and we can press on the gas again.

Mark MacLeod:
Yeah, it makes sense that you would be careful. Data can’t be mostly accurate. It just needs to be 100% accurate. That makes a ton of sense.

I often joke that an accountant would never start a law firm. And so you’re running a software company, but you’re not a software person. You had to navigate a very technical product for enterprise customers. It’s probably got 100 different bells and whistles and SLAs and all that.

So, two questions here. One is like, how do you lead the technology side of your business, not being a technologist, maybe start there as a first question.

Stephany Lapierre:
So I was fortunate that the first version I built with contractors, was very hands-on, and it gave me a lot of basic knowledge on development, and sort of the process of building your product and some of the technical challenges. My first CTO, once we raised institutional capital, was a very experienced engineer who had gone back to school and studied Big Data machine learning and a very thoughtful leader.

So I was fortunate that the first CTO that built what we now call the legacy platform was very experienced and very technical. Now, you know, other things were needed, like understanding the market so that we could provide feedback, you know, from a product perspective. And meeting customer needs was super important. So I had that, which was great, and getting those first few logos in. So we were a great team.

So Jeff laughed after, and I knew coming in that he was not the CTO that was going to be here after series A, it was very clear at the stage that he wanted to be involved. He was very hands-on on the keyboard. We looked for a CTO and we didn’t hire someone that at the time we were not looking to rebuild. And so I did bring advisors, our board was quite involved in that process to make sure we hired the right person. And, unfortunately, it didn’t work out.

And so, you know, lots of learnings, lots of time spent wondering what we could have done differently because it was very costly. But, yeah, it all comes down to the people who you hire and trusting those people. And what we ended up adding was more governance around execution.

But, yeah, I could have probably avoided some expensive mistakes if I was more technical, for sure. And I oversimplified technology. I think it’s magic. And so I will oversimplify things, which often, you know, needs to be broken down, and timelines are always too far out. I always think everything is possible. So I think it’s good and bad, right.? It has, again, a double-edged sword.

Mark MacLeod:
Yeah, I can see both sides of that. I mean, we see examples all the time of founders who, if they weren’t naive, and I don’t mean that in a bad way, would never, ever attempt to do what the company does. And so they’re blissfully ignorant and then actually do it. Whereas if someone had the knowledge, they’d be like, oh, no, that’s impossible. So I think it’s great to just think that anything’s possible.

You know, I’m reminded back in my CFO days, like early might have been my third or fourth startup. It was a very technical, scalable storage software company. And the CEO who was deeply technical, went on vacation for a week and he’s like, all right, Mark, you just run the company.

And like, I was trying to do stand-ups with the sales engineering team and figure out how we’re going to deploy a customer and check in with R&D on the roadmap. And like, they might as well have been speaking a foreign language. So, kudos to you for figuring it out, because I couldn’t. I was so grateful when that guy came back from vacation. It’s like, you’re never taking a vacation again.

Stephany Lapierre:
Well, what I find is like, and you know, I’ve heard this a few times where I want to be transparent with the rest of the organization or even our customers, and I hear like, oh, they won’t understand, this is too technical. And my view is that we’re a tech company, we’re a data company. If people don’t care to understand what constitutes the architecture of the data, the structure of the data, the complexity of it, or what a quality record is, you need to be interested or you shouldn’t be working for a tech company. That’s sort of my view.

And I tend to say don’t underestimate people’s ability to understand. Even if it sounds too technical, they’ll retain some component of it and it will make them also more confident when they’re in a position where they do have to explain or they have to answer a question. To solely depend on a sales engineer to answer customer questions versus having the credibility to say X, Y, and Z, and pulling in the sales engineer when you need deeper tech discussions around integrations or things like that, I think it’s really powerful.

So yeah, I would definitely suggest making that part of your day-to-day and making sure that people are interested in learning about the tech. And especially for us with data, our product is data. People don’t care about data or data quality. Yeah, like it’s, they shouldn’t be working here.

Mark MacLeod:
Yeah, exactly. That’s right. Have you explicitly tried to learn? Have you been just studying technology on the side or is it just happening through osmosis? Just through the process of building this company and product?

Stephany Lapierre:
I think it would be really dangerous if I learned how to code or do anything like that. So, no, nothing formal. I’m just curious. I do like to sit if I have an opportunity to sit in stand-ups or just listen carefully to some of the challenges, to develop a feature, or to hit certain milestones and understand the risk.

I think as a founder, you need to have. You need to be knowledgeable enough to be able to ask the right questions and then be able to step back out of it. But that’s something I’ve had to learn over time, is that it holds people accountable. If you know a few good questions to ask, they know that you relate and understand. Otherwise, they may gloss over things that are actually really important.

Mark MacLeod:
Yeah, that makes sense. You know, back to co-founders and the pros and cons, and you brought up a really good point. Like, half of marriages fail, and I’m certain half of co-founder relationships fail, if not more. But one thing the right co-founder brings is visibility. And, like, will be a mirror and be like, that’s bullshit, or, you know, just give you feedback. And, like, it’s so hard to get feedback as a CEO, and then, especially as a CEO, doesn’t have a close partner. So I’m just curious, like, how do you get feedback? How do you get input, and how do you keep getting better?

Stephany Lapierre:
So I think I’ve been, from the very beginning asking for feedback, and that was powerful when I raised capital to even understanding what the problem we’re trying to solve with customers. I love feedback. I ask for feedback all the time, and I tell them if we talk to customers, like, be transparent and constructive, that’s the only way we can get better. And it’s true for any conversations we have internally, I’ve been criticized for listening or taking too much feedback. But what I do when I ask for feedback is synthesize the feedback. And then there’s always a theme. There’s always a nugget or a theme that keeps coming back. Then I apply it to my situation and what I need to do and then use that to form a decision.

Because from the very beginning, I never raised capital, I never raised a tech company. There are some very basic questions that you need to figure out pretty quickly. I had to fight our trademark at some point against Facebook. I had to figure out how to learn a trademark, and we got our trademark. I mean, every learning is an opportunity to ask questions and ask for feedback. So, yeah, and sometimes feedback is hard to hear. And I’ve got multiple examples of that. And I say this to my kids, too. When someone says something, they believe it so it’s important to put yourself in their shoes and from their lens “Why do they believe that”? And then decide, make your formal decision if it’s, you know, from their lens and if it’s applicable or not. So there’s always a truth when you get feedback. It’s just understanding where it’s coming from and if it should be something that you prioritize or, you know, care to fix or change.

Mark MacLeod:
You’ve been at this company for nine years. It’s not the same company. Technically, it is the same corporation. You get your paycheck from the same entity in the same bank account, but it’s not the same company and therefore you can’t be the same leader. So, yeah, I love that you’re so actively seeking feedback. Not everyone does that.

Stephany Lapierre:
And every time I raise capital, there’s this big rush, right? Like, you run a process, there’s a lot of hype around it. There’s a lot of adrenaline. As a founder, you need some adrenaline. You’re someone who seeks some kind of thrill as you would never do it otherwise. And so it is a big rush. And then once you close around I always went through a transition because it changes the company, it changes the expectations, it changes the stage of the organization, and what you need to focus on. It changes the structure. Who do you bring on board? And so I always had a bit of a tough time in that month or two post-closing around to kind of reset, and it was sort of this very quiet, uncomfortable few weeks, and then to step into this new person that I needed to be for that organization at the time.

And we kind of went the other way right now where we’re growing really fast. And then as we re-platformed, we decided to scale back the team, we decided to scale back our go-to-market efforts so we wouldn’t spend too much money too fast before we nailed this new platform. And so we’re kind of back to being a startup mentality now, right? So, I had to shift so many times throughout this entire journey, and it’s really important to be adaptable to what the company needs you to be.

And so, right now I’m in front of customers, I’m selling with, you know, a very small go-to-market team and, but that’s what, you know, that’s what the job is right now. At some point we had, I don’t know, sales pods, CRO VP sales, sales enablement, sales operations, BDRs, I mean, we don’t have that right now for good reasons. And so, hopefully, all the learnings that we’ve got will get us to do this better. And I think it’s rare that you have sort of a second chance to grow the same company again, and we have that opportunity right now.

Mark MacLeod:
That’s amazing. So feedback is, is one of your inputs to help you grow as a leader. Are there others? Are you, like, a big reader, a big podcast person? Do you have a peer group, mentors, or coaches? Like, what’s the top of the funnel for Stephany?

Stephany Lapierre:
Well, I have on my wish list having Mark MacLeod as my coach. So I know you and I talked and I know it’s the wrong thing to say, like, all the investment, it’s always budget, or how do we go about this? And I don’t want to be frivolous with the budget that we have. And so I do think it would pay for itself, you know, many times to have someone to talk to that can help you get out of your head.

What I’d say is, I do read quite a bit. I do listen to podcasts when I’m commuting. I’m part of FreshFounders. So it’s a small group of fresh…

Mark MacLeod:
The Ottawa Group, right?

Stephany Lapierre:
Yeah! And we make small investments in early-stage companies. So I’m fortunate I get to talk to Solon and Kyle and other founders fairly regularly. I would like to be more involved but I can’t right now because the business needs me to be more focused. I’m less involved, but that’s been a great channel.

And then through stand-up ventures, I also have the fortitude of having other female founders. And so we have a stand-up circle that we try to meet once a month. And recently we’ve been together in person. And it was just really amazing to talk to other founders. Like, oh, I’ve got all these challenges. And you hear another founder, like, holy shit, maybe my challenges are not as bad as I thought because we all face different challenges, right? Like, it’s, there’s no easy journey and it’s really important to reset and to hear from their perspective what, you know, what challenges they face and vice versa.

I know that I learned a lot when I mentor another founder who’s asking me questions, and I’m like, you know, in my view, my opinion, my experience may not be 100% the same, but if there’s something that I’ve learned or so there’s a nugget that can help them in their journey, you know, I feel like I can give back because people have been so generous with me over the years and I’ve connected with a lot of people like my network from when I started to now, you know, for all facets of the industry, from advisors to investors to customers to thought leaders to general people that are cheering on from me. I try to make time for coffee, lunch, or even just a quick catch-up because I learn a lot from those conversations.

Mark MacLeod:
That’s amazing. Yeah, it’s funny. The Fresh Founders, I’ve had Kyle on this podcast and I remember when he just started and now he’s a part owner of the Ottawa Senators. Those companies clearly worked. And then Aydin from Fellow was on and he was one of the OGs.

Stephany Lapierre:
Such a nice person to talk about having someone who has a lot of humility.

Mark MacLeod:
Totally. And just the stories he was telling me about like the super early days of Fresh Founders where they’d get together with the Shopify guys and the second cup and the Shopify guys would be like, hey, we just figured out how to do AdWords because everything was new. So it’s just like an amazing group.

And then another truly amazing group that you brought up is Stand Up Ventures. And you know, I’m a limited partner in fund two and just a longtime friend of the fund. And I’ve witnessed, you know, I’ve been involved in many funds in different capacities. And the thing that stood out for me with Standup is the community, like the CEOs, truly want to help each other and you can just feel it. And of course, for those who don’t know, stand-up backs women-led technology companies.

So women are on the leadership team, have a meaningful position on the cap table and we don’t have to go here if you don’t want to. But I’m curious what your thoughts are, and what you’ve experienced as a solo female founder. Do you think there are challenges that are unique coming from that background? Are there gender differences in launching and growing a fast-growing company?

Stephany Lapierre:
Yeah, there are. I mean the numbers are there, but even if you say there’s none, like 3% of venture-backed companies are female founders, so there is a real gap in the industry. This is my view at least, I think generally it’s maybe not so much being a female founder as the risk profile that we may take on when we’re raising capital, that’s at least one lens of it. I always think if four women who had sold companies before, who had a complementary skillset, who understood the market well, and who had a big opportunity with a big TAM, would raise capital together, their chances of success would probably be significantly higher.

And unfortunately, a lot of women go on this journey as a solo founder, and they take on a lot of risks, and it’s risky if you’re looking, you know, being an investor and looking at a woman who has kids, who had never built a tech company before, who has this crazy idea that no one understands, but, you know, I don’t know that I would have invested in myself. Like, who’s this crazy chick? You don’t know what’s going to happen. You don’t know if the person has what it takes. Are they going to give up and go on to another idea? And I’ve seen this happen.

I mentored women founders who pivoted and went off to do something else and would not know the consequences. I know women founders who had kids who were sick for a period of time or needed them and their families needed their attention. So there’s a lot of risk for anyone starting a company and I do think being a solo founder is very high risk.

And, you know, when I was able to successfully secure capital, I found two executives, one a CTO, one a CEO who had successfully exited from companies, who had a background in my space, who put a check in the company and brought in other investors, and that lowered my risk profile. And that’s when Stand Up Venture was like, okay, we’re going to invest. And so I do think that has a lot to do with it.

Women tend to overshare and answer questions maybe a bit differently. And so part of my mentorship with women founders is changing a little bit of the narrative when you’re raising capital and recruiting talent. And I had definitely that in the beginning, like, I need money to grow my company, while investors are like, I don’t care about that. I’m going to give you money to make a lot of money. What makes you think that you can give me a 5x or 10x return on my investment? And do you have what it takes?

And so changing the narrative, and this guy, I said this on a podcast recently where this founder was, like, in his late twenties, he was wearing a baseball hat and a hoodie, and he’s like, Steph, you just have to be cocky with investors. Be cocky with investors. Like, I don’t have that. You know, I’m 46 now. I was in my late thirties and I had three kids. You know, that doesn’t apply to me.

But the feedback was, how do I change the narrative to let investors know about the size of the opportunity? Like, why is this happening now? What market are we attaching ourselves to that is growing really fast? How big is the TAM? For us it was we’re the zoom info to the buy side of the digital enterprise and suddenly our TAM is $62 billion. We’re attaching ourselves to the BI and the source-to-pay market that are growing X and we have the expertise, then it’s the proof points and it’s almost like you’re crazy if you don’t invest. We’re going to find investors and you’re going to miss out on this opportunity and so on.

Changing the narrative gave me the opportunity to raise capital and create a bit of FOMO around the fact that we were raising money. So those are kind of examples, I think, of what I’ve seen women sort of get trapped in and again, feedback and looking at yourself in the mirror from the eyes of an investor. If you’re putting yourself and you had the money, like, what would you need to see from a founder to be able to say like, hey, I don’t want to miss out?

I’m going to put 20 or 100 or, you know, $5 million on that business because I genuinely believe that they have the best chance of winning in this market and giving me a big return. So it’s a different mindset and guys are better generally at that. What I’m saying is that guys can be cocky. Have the persona with the ego to carry that narrative. As women, we tend to be a little bit more cautious or overshare or humble, which doesn’t always translate into like, hey, I’m building this massive company, I’m solving this massive problem and you’re going to miss out.

Mark MacLeod:
Yeah, yeah, 100%. And, you know, if I buy shares of, I don’t know, Shopify today, I can change my mind tomorrow and sell them. But when I invest in a startup, I’m in for a 7, 10-year journey. And so it’s a high-risk decision. And then investors have this thing called agency risk, meaning like, you are their agent to deliver them returns. It’s not about them. They’re just kind of along for the ride. For the most part, they try and help, but they succeed through you. And so they’re always looking for confirmation as to whether this is the right decision. And they’re doing it before they invest, but they’re even doing it after they invest.

And so this brings up like, I’ll bet you every VC I would ask would be, yes, I wish my CEOs would ask for more feedback, but it’s sort of perverse. I bet you’re saying you can always ask for feedback. I can almost see them saying, on the one hand, this is good, but does she lack confidence? Do I have the right leader? So, a strength suddenly becomes a concern. I can tell you, for me, like, I only coach people who are highly self-aware. Cause otherwise I’m wasting my time, right? You’re gonna go through learning and growth every single day, not just the days you meet with a coach. And so, another side of confidence that is needed is cockiness and if you think your shit doesn’t stink, well, you’re just not going to be learning, right? You’re just not going to be open to feedback. Someone’s going to give it to you and be like, they’re wrong and you’re just not going to see it.

Stephany Lapierre:
Well, I invested in Chloe Smith of Mercator.AI, and I know her space cause it’s relatively synergistic with what Tealbook does, but it’s catering to very different markets and use cases, I don’t know that space and what problems she’s solving, but when we interacted, she asked really good questions. And then once we hung up the phone, she sent me a follow-up on all the questions I’d asked with very specific next steps or information that I asked her. But I knew one she asked a really good question. She also followed up and was very pointed about the questions I had to make sure I had the answer and then proceeded to give an update to all of her investors in a very detailed, humble, very open, you know, it’s not all rosy, there are some challenges, but to me it was more about her, right? She’s coachable, she’s listening, she’s willing to make the changes that she needs to make or do what it takes for the business based on what the business needs. And that’s what I would want from a founder. And that’s what I got from the very beginning.

If you asked Michelle McBain, she’d probably tell you, like, Steph was very coachable. Like, she was listening and she was applying. Not everything. And I certainly don’t want all my shareholders to call me to give me feedback, but the ones at the time that I need it, I’ve been stepping up, and I’ve been very valuable. And the other ones, you know, I’ve managed because I do have quite a lot of angel investors. And so from the very beginning, I set up to say, don’t put your life savings in my company because this is high risk, and I’ll do whatever it takes to make the company successful. And I promise I’ll give you updates, but, you know, if I get calls or text messages all the time, I’m not focusing on growing the business. And if I need you for your network or whatever reason, I’ll make sure that I contact you.

So, setting expectations upfront has been really valuable. And I’ve heard nightmare stories of, you know, sometimes it’s the investors who wrote the smallest checks that are the ones that are the neediest and have the most things and suck some of your time.

Mark MacLeod:
Absolutely. You know, CEOs always ask me every time they’re doing a round and someone wants to be an observer as an example, I’m just like, dude, like, observers don’t just observe. If they’re on the call or in the room, they’re gonna speak. They’re gonna call your directors afterward. They completely influence the dynamic. Like, yeah, they’re not benign, you know, and, yeah, I’ve seen the same thing. Small angels, just like, yeah, get some kind of Google news alert, and then text the CEO freaking out, what is this, you know?

Stephany Lapierre:
Oh, yeah. I said that recently in a podcast where I told an investor I was going to send his money back, and he was like, what do you mean? And I said, I can’t be answering your text message. If you’re nervous about the check, which I get, it’s a lot of money, but if you’re nervous about it, I’d rather give you the money back. And then he left me alone. And once in a while, like, being like, hey, just checking in. How are you? Be great to get on a call. But, you know, he’s been good about it. But it required that at the beginning. It’s like any relationship. What expectations are you setting with your investors and your board right out of the gate? Because it can. Yeah. It can be a slippery slope.

Mark MacLeod:
Yep. Yeah. As we start to kind of wrap things up, maybe a couple of final questions. One is, you know, you recently brought on a right hand to kind of run a bunch of the business. And I’ll bet you many people listening, once they’ve gotten to a certain stage, have contemplated that and there’s a, you know, a huge element of trust in it. I would love it if you could just walk us through how that happened and how you got to the comfort level to turn over a major part of the business to this person.

Stephany Lapierre:
Yeah, I wish I’d done it years ago, frankly. I know my strength. You know, I can, I can sell TealBook. I can get people excited and passionate. I know where we’re going. I’m also really good at diagnosing. I hear things and I know there are gaps. And so all the areas that need attention kind of rise to the top, and I’m less good about sort of how do we resolve it or putting a process in place.

And so, I’ve been looking for someone like that for a long time. But it was always that, do we need that? Like, if I have executives and they’re accountable and they’re operational, you know, should that satisfy? And it was, it was the same with a chief of staff. Like, I looked to hire a chief of staff and waited and waited. And until I did hire a chief of staff, I realized I should have done it before. But, yeah, we hired Phil Garlick as president about five/six months ago. I had almost hired someone two years ago, and it was the wrong fit. And so I got excited about it and then as we continued in the process, it felt that it would put us in the wrong direction as a company.

And I was worried the culture change was going to be too dramatic. But I had met Phil seven years ago when he was at ZoomInfo and the first version of Tealbook. I tried to buy data from ZoomInfo and DNB. And I remember thinking like, oh, this guy is sharp. Like, he just seems like a good person and very experienced in the data industry. So I tried to get him to invest and join my board early on. He introduced me to now one of our independent board members, Marty Khan. And then we got reconnected almost a year ago now.

And I was seeing sort of gaps on our go-to-market side, that it was harder because I had executives that were more experienced than me in some areas. So it’s harder to push back when you don’t have the same experience. Even if the person reports to you and it’s your vision, you’re the CEO. And so I needed someone who had more experience to call out the things. And in that process, you could see the team finding what you had to bring to be valuable. It was a good fit from a culture perspective, and it was a moment where I needed that day. Do you want to take the reign? Cause I’m good.

You know, I asked him what his plans were, if he was looking to sit on boards or do advisory work. And he said that he still had the energy and would join a company if it was the right role in the right company, and asked me what I had in mind, I said I could really use someone to take the day-to-day operations, and then that would allow me to shine and focus on the areas that I’m good at. Cause when I’m diagnosing something, then I can relate to him, and then he can investigate. He can help enable the team to come up with a solution versus me trying to be in so many things and it’s a much better formula.

And I can interact differently with my customers, I can interact differently with a team. I have more time to think. I’m involved where I need to be involved, where I can accelerate things by contacts or by industry experience. So, so far so good. It’s only been six months, but I feel fortunate that I was able to find someone like that.

For some people, there’s a term for the enabler or the integrator, sort of the founder that is more visionary and then the person that’s more on the business side, especially with the experience that he brings in. We were already making changes to the structure, our user experience, and how we’re packaging the data because of his experience. So I think it’s going to significantly accelerate us.

So, if you’re on the fence and you’re thinking about it, it’s probably because you need it, and just finding the right person is hard. It has to be a good culture fit. And the team rallied around him really quickly, which felt different. It’s definitely a change for me, but, you know, it’s a change that I think is a really good thing for the company and the business. So then for me, I think the long-term will also be beneficial.

Mark MacLeod:
Yeah. Just hearing you talk about everything he brings, seems like it brings you and the company just tremendous leverage. So, yeah, really strategic.

You brought up something really important that a lot of people struggle with, which is one of the things that, one of the reasons why you’re interested in Phil, it’s because you’re managing leaders who are experts in their field and you hesitated to push back. And so I’m curious, in those situations did your gut know that they were going in the wrong direction and did you not listen to your gut?

Stephany Lapierre:
Yeah, many times. Actually, more times than not. And over time I have learned to push back. And there’s sometimes a good explanation, but if I, if I get the explanation and I walk away and I’m still feeling this way and it’s not changed my perception or my, my hunch on something, the dangerous part is when you start digging in, and that’s what I had to do a few times, is start to understand.

Like, one example is our ACV was getting smaller, and our cell cycle was getting longer and all I could hear was that it was the market. And so I’m not saying that the market did not influence some of those changes, but what I was not hearing is what we’re going to do about it, what’s within our control, what we need to change to adapt to the market if the market is challenging us competitors or shift in priorities.

And it was sort of like we’re doing everything perfectly, but the market is, which I was like, I smell bullshit. And it’s hard because then you’re like, okay, well, how am I going to understand it? And so I had to sit on calls and start listening to what was happening. And that’s hard because then the other person gets defensive if they’re not humble. And it’s happened a few times in my journey where I’ve had executives that had an ego or for whatever reason got in the way and ultimately it never ended well.

And so where I’ve done well with executives is the ones that are humble and they’re willing to go outside of their role to understand, you know, what they can do differently, bringing best practices, being willing to take more responsibilities and acknowledge when maybe it’s not the right responsibilities for them. So it’s that self-awareness and people that are there for the right reasons.

And so I’ve had some amazing experiences, and people are not with us anymore for various reasons. And, you know, I will always stay in touch, and I’m so proud that they’ve been able to go off to other companies and get more experience and continue to grow in their journey. That’s a big part of hiring people and letting them go. And then, you know, we’ve got people that are still with us today that I’m so fortunate to have worked with for a few years and are still very committed to the mission.

But yeah, I think that gender may play something in it, too, because I don’t have a big ego, I don’t stump my foot, I don’t scream at people, you know? I process things, and I do think that made it more challenging for me as a leader. And I learned so much from Phil just by how he’s asking questions, how he’s driving accountability. And I don’t know, there’s sometimes I’m like, I don’t know if I could do it even in my version of myself, the way he’s doing it.

And I don’t know if it’s a personality or gender thing. I have not solved that yet. But the version of that for females is often perceived as she-man or whatever it may be, and that’s not me, I’m not a bitch. I don’t scream at people. And so, being more firm, setting expectations, driving accountability for people, is super important. So finding within my personality, how do I ignite that without offending or hurting people’s ego, you know, along the way?

Mark MacLeod:
Yeah, 100%. Listen, we get what we tolerate, and so you have to have high standards, but in your way, you don’t have to become someone you’re not. And I think the only way you can go through a journey that’s nine years in and you’re still in the middle of this, not at the finish line, is by being yourself. I think when people try and put on a mask and try and be, oh, this is how I should be, that they just hate themselves.

Stephany Lapierre:
They serve the wrong type of people. Ultimately, when I look around, the table. Now we have really humble people, very committed. It just took time to find that shape and understand how you hire people. I’m very trusting, and that’s sort of good and bad. You know, I wish I was less trusting and the trust was earned over time. It’s the opposite for me. I give all my trust, and it’s for yours to lose. And then when it starts to go away for various reasons, that’s where it’s been more challenging to navigate those relationships.

Mark MacLeod:
Yeah, no, I get it. Listen, I think solving for humility is the right way. I think ego is a complete kryptonite. And if a company is doubling every year, a leader has to grow in their capacity every year. And like I said earlier, I just don’t think they do it if they think they’re great.

So it can go the other way and you can be insecure, and that slows you down. So, as with everything, it’s a balancing act. But leaning into humility is great for me. And then also building a company around you. Leaning into your superpowers, who you truly are, and then surrounding yourself with people who align with your view of the world. That makes it worth doing because you probably spend most of your waking hours doing this, so might as well enjoy it.

Stephany Lapierre:
100%. And tricky. When we scaled really fast post series B, we hired a lot of people, made lots of mistakes, and scaled too fast. And so, again, sort of had the opportunity to do that again, which is a bit of a gift, because then we can reset on what kind of behaviors we want to see. We always had these core values, but living in those core behaviors and values as we’re looking for new talent to come in with the right mindset, the right skills are important, but it’s more important to have the right mindset. And I’ve learned that the hard way. Lots of war scars.

Mark MacLeod:
Yeah, absolutely. (laughs)

Stephany Lapierre:
I’m hiding my gray hair. (laughs)

Mark MacLeod:
That’s right. I love it. Well, Stephany, this has been fantastic. I get to sit here and ask, like, a hundred more questions, but I know you got a company to run. Thank you so much for making the time. I appreciate it.

Hey, thanks for listening to the Startup CEO Show. If you’d like to connect with me, be sure to visit my website at markmacLeod.me, or follow me on LinkedIn at The Mark MacLeod, or X account @markmacleod_, and if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We’ll see you next time.Hey, thanks for listening to the Startup CEO Show. If you’d like to connect with me, be sure to visit my website at markmacLeod.me, or follow me on LinkedIn at The Mark MacLeod, or X account @markmacleod_, and if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We’ll see you next time.