Raising over $2.5B in Startup Funding & Getting Acquired by AMEX [Founder Story]

In the world of fintech startups, few stories are as inspiring as that of Kathryn Petralia and her journey with Kabbage.

Back in 2008, Kathryn and her founding team set out with a visionary goal: to leverage technology to provide small businesses with the funding tools they needed to grow and scale.

Kabbage quickly evolved, transforming from a simple loan provider for SMEs to a comprehensive cash management solution for entrepreneurs and founders.

My co-founder and I had the privilege of sitting down with her to discuss her experience for an episode of our podcast, The Startup Journey.

But, in case podcasts aren’t your thing, I wanted to publish a written version to go with it.

It’s a remarkable journey that saw Kabbage raise over $2.5 billion in funding and ultimately be acquired by American Express.

In this interview, Kathryn shares insights on:

• Validating the Business Idea: The initial steps and strategies employed to bring Kabbage to life.
• Achieving Product-Market Fit: The trials and successes in aligning their offerings with market needs.
• Navigating Investor Relations: Lessons learnt from the complex world of startup funding.
• Building an Early-Stage Startup Team: Key insights on assembling a team that can drive the vision forward.
• Work-Life Balance: Balancing the demanding nature of entrepreneurship with personal life.

The Idea for Kabbage

Rui: To get started, how did the idea for Kabbage come up?

Kathryn: My co-founder, Rob, actually had the idea for Kabbage. Everybody presumes it’s going to be a story about how we were running a small business and couldn’t get financing, so we started this company. But it really had nothing to do with that. It was all about the technology. eBay had recently launched an API that allowed third parties to access seller and transaction data. And he thought, ‘Wow, I wonder if you could use that data to underwrite a loan to a small business.’

I’ve been in FinTech for a long time, even though it wasn’t called that then. And I said, ‘Well, that’s pretty cool. I love using technology to solve interesting problems and to do new things.’ And so that’s how Kabbage was born. We started out just making loans to eBay sellers. If you had a pulse and an eBay account, we’d give you 500 bucks, pretty much. That’s how that worked.

I have to say, a lot of them didn’t pay us back, but we figured out who would pay us back over the years and then built out the platform to provide lots of other cash flow management solutions to small businesses. And then there was the pandemic, and then we sold to American Express. So that’s the short story.

R: When did you decide to go 100% in? Your co-founder called you, he had this idea, were you in love with the idea right from the get-go? Did you jump straight in, or was there a process there?

K: It’s not just about the idea. I did think the idea was interesting. I was actually at another startup that I had not founded but was involved in from their early days.

For some reason, this idea just seemed like the right thing to do. Also, my co-founder, Rob, seemed like a great person to start a company with. We laughed a lot, had a lot of fun, and cared about the same things.

It’s interesting, you don’t just quit your job and then suddenly spend 100% of your time on this new business. You’re kind of working on it, maybe working on some other things, and you’re not sure what you’re going to do. Then one day you wake up and realise, ‘Oh, I guess I do this full-time because I do this all the time now.’

So it’s sort of this gradual process.

R I can relate to that. And how did you meet your co-founder?

K: We actually met in 2005. His company was doing intellectual property discovery work with customers, and I was one of his customers. So, we are actually listed on a couple of patents together from 2005, from the work we did together. And that’s how we met.

The Road to Product-Market Fit

R: Can you share some of the key moments from the journey from the moment you had that first version of the product to the moment you raised your first meaningful round?

K: Product-market fit is a really funny story for Kabbage. I always say that we’re in the world’s second-oldest profession.

We never had to convince anyone that they needed money. All small businesses need access to capital. When you’re selling money, it’s a really easy sell. The question is, can you sell money to the people who are going to return it to you one day?

For us, it’s funny. We had an angel investor early on who said, ‘Why are you guys building this technology platform? Why don’t you just call up a bunch of businesses and see if they want money?’

We told them, we’re not trying to prove that people need money. We’re trying to prove that we can build a system that can automate it for people who don’t normally have access to these types of platforms and products.

What was interesting was we didn’t know how big the problem was and we didn’t realise how important it was. We didn’t realise how few small businesses were being served in the U.S. There are 30 million small businesses; 90% of them have fewer than 20 employees, and 80% have fewer than 10.

We’ve always served that long tail, but banks have a hard time serving them because they just don’t have the tools to do it.

It’s expensive. It costs the same amount of money to make a $5 million loan as a $50,000 loan. So why wouldn’t they just focus on the $5 million loans? That’s how they’ve looked at it. It’s not because banks are bad or because they don’t care about small businesses. They just didn’t have the tools to do it. So that’s what we wound up building. And we all know how important small businesses are to local economies.

Lessons on Raising Money

R: Changing gears a bit, to your point, money is vital for every business in the world.

Especially when we’re talking about startups and entrepreneurs starting a business. It’s a critical moment and there are some common misconceptions there.

Can you share some of the most important lessons you’ve learned on how to deal with investors and raise money? Since you got that beautiful figure of $2.5 billion and went through the whole series.

K: We covered a good part of the alphabet.

I think we raised through Series A. The first investment we received, actually, we got into this little local event called Venture Atlanta. We’re based in Atlanta.

We got some investors who were a bit anxious and we didn’t know who they were, but they gave us a term sheet and we were like, ‘Well, okay.’

But we used that to get another term sheet that we were more excited about and wound up going back to another investor that we had met with previously for our seed round who had turned us down.

We said, ‘Well, here we are, we’ve got 50 customers on the platform, the system works.’ And he was like, ‘I’m in.’

What he wanted to know was not just a product-market fit question, but whether we could actually do it. Can you get people to sign up? Can you approve them? Can you build a system that can do the thing you said it could do? And it turned out we could. That led to the very first investment.

After that, the rounds came pretty quickly because the initial rounds are smaller, you’re scaling up, and you’re spending money.

We were really fortunate to have some great investors who knew FinTech. What they said every time was that they were investing in the concept and the opportunity, but they were also investing in the team.

“Team” is really important. We always said that they wanted to join the party because, as I mentioned earlier, we always had a good time together. We thought it was fun to do the work, and I think that was contagious.

R: I’d like to ask about that angel investor who refused you the first time.

What did the company look like then? What did you present to him that made him refuse?

Because there’s a point to be made here around investors looking for traction and your ability to execute much more than just a good idea. So what did you have in that first engagement?

K: Basically, we pretty much had a napkin idea.

We just had an idea and were like, ‘This is it. What do you think about this idea?’ That’s why a lot of people said no. Over time, we just cajoled and coerced lots of people.

I think many invested in our seed round because they were just exhausted by us asking them for money. They were like, ‘Fine, fine. Here’s some money.’ It’s really hard to raise money on an idea alone.

R: Persistence obviously plays a big role as well. We talk about this often because we work mostly with entrepreneurs, and the common misconception is that you can go to an investor with a brilliant idea, and they will immediately understand.

I have one question not related to the seed round but to scaling up. From Series A onwards, is it just about the numbers and the economics that you bring, or is there something else that investors pay attention to to give you money?

K: Of course, they want to see that the numbers are moving up. I mean, no pro forma, no P&L ever looks exactly like you think it will. You’re always behind, always, always, always. They’re not necessarily expecting you to hit all the numbers, but they do want to see growth, and I think that’s important.

But they also look at the market. Who else is out there? What are they doing? How are they doing? What are the connection points between this business and other businesses?

We were fortunate to be growing up at the same time as a lot of other FinTechs serving small businesses.

Whether you think about a company like Coupa or Square, PayPal, of course, was doing extremely well and doing a lot in the space. They could see that those were our cohort, the teams against which we were playing.

The Early-Stage Team

R: Who did you have with you in the early days? What was the team composition besides you and Rob?

K: We had a third co-founder whose background was in technology startups and was also great on the money side of the business.

Our first hire was a bit of a challenge. We had a hard time hiring someone in technology to build our platform because we were all non-technical.

We were comfortable with technology and knew how to identify solutions to business problems, but we didn’t know how to write code, architect a system, or choose a platform.

We eventually hired this unbelievably bright, super insane dude who built the whole thing by himself in six months.

It was a crazy time. We kept thinking, ‘Wow, this is taking so long. What is taking you so long?’ In retrospect, we wondered how he managed to do it so fast by himself. We hired him in late 2009, and by late spring of 2010, we had our first demo ready.

We showcased it at a conference called Finovate, which was only a couple of years old at the time.

I always enjoyed this conference because I liked learning about new technologies, but doing a live demo was terrifying. Who does a live demo?

Dumb people do live demos, but we did one. I was in the back, testing it over and over to make sure it would work. Miraculously, it worked on stage.

We were scheduled right after Aaron Patzer, who had founded Mint and was like the godfather of FinTech at that time.

We thought, ‘Oh my God, we’re going on right after this guy with a live demo, and it’s going to suck.’ But it worked, and it was cool. We never did a live demo again after that, but it was a great experience.

Mike, our first engineer, built the system himself. We also hired a super young kid fresh out of school who could do just about anything and became a critical part of our data science and database engineering teams.

We needed someone to help with financial operations, so we had that person early on and eventually hired another engineer. That was our core team for a while. After Series A, we realised we needed to start hiring more people, and that growth was rapid.

In startups, there’s a lot of turnover because you bring people on for a specific moment in time. Sometimes they don’t want to be there for the next phase, or they’re not ready for it, so you have to bring in new people.

Over the last 12 years, even now at American Express, I’ve spent most of my time dealing with people, managing them, finding the right people, placing them in the right roles to be successful, resolving disputes, and making sure everyone has what they need. People are your business, and they are a critical part of running it.

R: I have a bunch of follow-ups.

So first, I’m interested in knowing about Mike, because as you can imagine, being a product and software house working mostly with entrepreneurs, we are this tech partner to a lot of the founders who are starting out now.

How was it that you found Mike? What was that like? Where was he? How was the connection made?

This is a valuable lesson for anyone in the ecosystem. We actually advocate that if you can find a technical co-founder or a CTO from the get-go, you should.

It’s really hard for non-technical people to bridge the gap with the technology part, especially with just an idea or a very small product at the beginning that might not be able to convince a good tech talent.

K: I think we were really lucky.

I had worked with a woman who had been an amazing recruiter at a company where I worked previously, and her focus was on hiring engineers.

She had gone off on her own and was doing her own consulting work, so we hired her to help us find our first people. I can’t understate just how important that was.

She’s the one who brought us a slate of candidates, and we talked to them all. I liked the one who was a little different, someone quirky who I thought would fit into the hectic and frenetic environment that is a startup. That’s how we found Mike.

R: Having that person serve as somewhat of a headhunter and then doing the recruiting based on a personality match, which I agree is crucial at the start.

Otherwise, there will be too much trouble to handle. If you already have those blockers on personality, it’s going to be even worse.

K: We had a lot of arguments about it, though. I mean, not a lot, but the founders argued a fair amount about whether he was the right guy and if we should get someone else.

But frankly, we were all operating from a position of ignorance, so we were just rolling the dice.

Growing the Team & Transitioning to a Larger Startup

R: As entrepreneurs, we will never have all the information. It’s all about having as much as possible so we can make educated guesses, and then it’s learning by doing.

You mentioned that after Series A, you started recruiting. So I’m assuming that in the early days, you were doing a bit of everything, right?

And then after Series A, when you got some money, you started growing the team.

How was this transition? One of the major risks there is a loss of culture. It’s really easy to create an environment that is vastly different from the one you start with.

Any pointers for founders going through the same situation?

K: Something that we did then, and still do now, even when we had 600 employees, is we interviewed every candidate ourselves. At first, it was about figuring out if they were going to be good at their job, which we weren’t necessarily good at early on. Then it became more about whether they would be a good fit for us.

For us, it meant finding people who were self-aware and could be themselves all the time. We were always ourselves — silly, quirky, emotional, and all the things that people are.

We wanted people who could feel comfortable being that way too. That interview process helped, and we got good at identifying people who might not be a good fit. Maybe they weren’t comfortable dealing with lots of different kinds of people, or maybe they weren’t as self-aware or didn’t know their faults.

We developed a quirky list of interview questions that we always asked everybody. One of my favourites is, ‘What’s the one word you’d like on your tombstone?’ It tells you a lot about how people either see themselves or want to see themselves.

Recruitment Advice for Startup Founders

Paolo: On that, I have a question regarding recruiting.

Did you follow any specific framework to hire? Do you have any practical suggestions for founders who are feeling a bit lost in the cloud when recruiting, especially for the first few people?

K: You have to find someone who can help you, someone in people ops (or HR, as some call it) who can help you design the framework for the organisation that you need and then constantly restructure.

We were fortunate that the woman I mentioned, who helped us find our first head of technology, joined us later on. She was with us for many years and built out our entire “People” system. That was critical.

You need to have a strong partner who can help you find people. It is great to go through LinkedIn — we found a lot of people through LinkedIn by looking for particular skills — but you also need someone who can sell the company for you.

Often, you want to come in as the backup salesperson because, especially when you’re a startup, you’re convincing people to join you on this crazy journey. You want to have a couple of different voices that people hear.

In our case, we were hiring a lot of engineers, so it was important to have someone who could speak the language of engineers. I think that partnership was super critical to getting us where we are or were.

P: And I imagine if you hire the right people, the first three or four right people, and then they speak about the company, as you said, they sell the company.

So they will convince others to join, and you’ll have, let’s say, a viral effect of having very highly effective people in your company.

K: We were also really lucky that we were based in Atlanta, which was certainly a fintech hub for payments, but there weren’t a lot of startups.

So, we had this unique, quirky environment where people could come and be themselves. They could wear shorts if they wanted to, or flip flops, or no shoes. We brought in food, and there was beer. That’s not culture; that’s just creating an environment that makes you comfortable.

Culture is about the people who come into the organisation and what they bring to it. Sometimes people confuse that.

Speaking of fintech, banks might create an innovation hub with a pool table and a fridge with six beers in it and think, ‘Oh, we have culture. It’s startup culture.’

But they don’t, because they don’t have the right people.

A “Day in the Life” of a Startup Founder

R: What was a day in your life back then? How many hours a day, and days a week were you working, and how was your focus split?

K: I mean, you work all the days and all the hours.

My husband and I have been married for 29 years. When we started Kabbage, we had an eight-year-old, and he also came to the office.

When we worked on the weekends, he’d come into the office and hang out, and so would my co-founders’ kids. It became a place where family was welcome, not just for us but for everybody. That made it easier and more fun. We had Nerf guns, ping pong, and stuff that the kids could do.

You just work whenever you need to work, and it ebbs and flows. A lot of the work doesn’t seem like work — it’s talking about your company, being on the road raising money, attending conferences, speaking at events, and doing media.

All of the conversations you have about your company are important work. Rob always said, ‘It’s our job to get out and talk about Kabbage as much as we can to as many people who will listen.’

And that’s what we did. I think that was a really important part of the traction we ultimately gained.

R: This is an eternal debate, right? About work-life balance and whether you should work 80 hours per week, 40, or whatever it takes to be balanced.

I’m hearing more and more, and believing more and more, in merging work with your personal life.

If you have your kids there and if that’s what gives you pleasure, it makes a difference.

My father once told me that I should find something I really like to do and then I wouldn’t work a day in my life because it would just be things that I enjoy. So, I completely align with that vision.

K: More than that, make crazy decisions and do crazy things.

My husband and I decided six years ago to have another kid, so we have a four-year-old who’s almost five now.

Everyone was like, ‘Oh my gosh, what are you thinking? You have this company, it’s growing, you’re busy,’ and I was like, ‘Nope, we’re having a baby.’ So, we had a baby.

As a side note, I’ll tell you what, it’s really boring to be eight months pregnant in Vegas.

Key Startup Lessons

R: I can imagine (smiles and laughs).

I agree, if you’re going to wait for the perfect moment to have kids, you won’t ever have kids.

You have more, you give more; you have less, you give less.

Now let’s look for key lessons on specific things. So, one key lesson you learned on product building.

K: This is an interesting topic for us in particular. As long as you have founders at a company, product development is weird and hard, especially if you only have one product.

We had our line of credit product, and that was mostly what we did for six or seven years. When you only have one product, it’s often led by the founders.

When you hire product people, especially from big companies, they’re used to owning the P&L and the whole vision for the product. This can create conflicts.

You have to be extremely aware of what you want to give up and what you don’t want to give up when you bring in someone to run the product for you.

We’ve hired many lovely people on our product team, and it took us a long time to find the right balance.

It also changed once we added other products. A multi-product organisation operates very differently from a single-product organisation, and you need a different structure to support that. We had to figure that out too.

We didn’t do it right the first time, and we probably aren’t doing it perfectly now, but you try as hard as you can to make it work.

The key thing to remember as a founder is that you probably care about the product more than almost anybody. Even if you have amazing people, your voice is louder, and they’re going to listen to you whether you want it to be that way or not.

R: That brings up an intriguing question. When you transitioned from the early days with just you and your co-founders, to the post-Series A phase where you began scaling up, how did you manage relinquishing control over many aspects of the company?

Was it challenging to start delegating and empowering others to take on these responsibilities? Did you find it difficult to let go, or were you comfortable with delegating because you trusted your team?

I’d love to hear your perspective on balancing ownership and delegation, particularly during the initial stages when your team is small but you’re not alone.

K: Early days are very different, and you have to do everything because you need to know exactly what’s going on.

There’s only five or ten of you, or whatever it is, and you need to understand what’s happening. As the company grows, you must delegate.

One thing I tell people all the time, especially now when I interview people every day, is that I’m not trying to figure out if you’re good at your job.

I’ve never done your job before, and I’m never going to do your job. Most of the people who work for us do a job I don’t understand. So you have to trust the leaders of those people to do their jobs, that they’re really good and that they’ve done that job before.

Our leadership team is incredible and so strong. Heading into the pandemic, we let go of half of our staff because we were serving small businesses, and we weren’t sure what was going to happen next.

It was a terrible experience for everybody. The people who stayed went on virtually to build a system that provided more PPP loans to small businesses than any other bank in the country, except for Bank of America.

We were the second-largest PPP loan provider, and the PPP is the Paycheck Protection Program that was launched as an aid to small businesses in the early days of the pandemic.

This team worked their faces off. I spent weekends talking to customers on the phone and processing loans just like everybody else. It was an amazing experience where we all just pitched in, and it was our leaders who passed that on to their teams.

You have to trust your leaders, and your leaders have to be able to get their hands dirty. They can’t just be people who sit and opine and read PowerPoints, and their people can’t just be people who make PowerPoints. They have to be people who do things.

It was a really hard challenge for us over the years to bring in people who were experienced but also knew how to do stuff. They knew how to do the work.

People who had been at large companies for a long time would often say, ‘Oh, I’m so excited about the startup. I can’t wait to get in there and do stuff.’ Most of the time, we found they didn’t know how to do stuff because they had done it a long time ago but had kind of forgotten.

We had this amazing balance of leaders who knew how to do things and also did things. They cared about the people and the customers.

R: Yeah, absolutely. I can relate to that a lot. So what’s the most important: people, customers, or the product?

K: That’s a great question. You have to do the right thing for the customers, but you can’t do it without the right people.

And the right people are going to build the right product if they care about customers. I don’t think you can say it’s mutually exclusive. It’s not a zero-sum game. They’re all important parts of the ecosystem and the flywheel.

R: That’s the equation, right? That’s absolutely the equation.

That leads to the second question regarding these key lessons, which is marketing. Early stage, finding early adopters — what was that like?

K: Well, as you know, it’s like handing out candy to children. You’re giving money and time to businesses that nobody cares about.

We would go to these eBay On Location events where eBay sellers would go to learn from experts how to be better eBay businesses. We would throw parties, be at a bar, and buy people drinks. If we bought someone a beer, you would have thought we bought them a Tesla.

They were so excited that someone was excited about them, that we cared about them and thought they were legitimate businesses.

That was a vital process for us — learning how to talk to, understand, and serve these customers because they were underserved.

R: It’s all about empathy, right? You genuinely cared for them and showed interest in their problems, finding a way to solve them.

You have no idea how many founders we speak with who believe in their ideas so much that they forget to see if the market thinks their idea would solve it.

You can have the best team in the world and the best product, but if the problem isn’t there or people aren’t incentivised to solve it, it simply won’t work.

Are there any key lessons you’d like to add on people and hiring? I know we’ve discussed this quite extensively already.

K: The only thing I’ll add is that people want a career path.

They want to know what their next step is going to be, no matter how much they love startups or unstructured environments.

It’s hard to give people a path at a startup, so we told folks, ‘Every six months you’re getting a promotion, whether you want it or not,’ because the business is growing and scaling, and your work is getting harder.

We pushed really hard against hiring people and building fiefdoms. We pushed hard against titles.

We had a very flat organisation with no titles — you either did a thing or you were the head of it. That was important because we didn’t want the hierarchy that comes with it.

Everyone felt equally valuable, whether they were on the phone talking to customers, supporting the technology our employees were using, writing code, or being the CFO. It didn’t matter; everyone felt the same. I think that was really important.

R: Who was responsible for that? For the decisions around the career path at the start. Did this happen after you onboarded someone managing HR, or was this the work of the founders?

K: It was Amy, the lead of our people and ops. She identified the need, talked to people, listened to them, and helped us constantly change the career path because you’re always changing what the path is depending on what the business needs.

When you go into a new line of business, suddenly you need somebody doing something else.

We were always asking, ‘Okay, who do we have internally who can do this job?’ So, we had a lot of people move from entry-level customer-facing roles into other roles.

Every part of the company had someone who started in an entry-level role, and that was really important for us to grow people. The fact that they saw this gave them more comfort that there was a path for them.

Our head of technology, David, is amazing. He has been with us for a long time, I think nine years. He joined us as an engineer, then became an engineering lead, and then he was managing all the engineers before becoming the CTO.

It was a long path for him, but everyone sees people who have done that, and it tells them that it’s possible for them too.

R: Earlier in the conversation, you talked about having high turnover and the efforts required to manage that problem in startups.

From the first engagement, where it’s just you as the non-technical founder onboarding a technical resource, up to wherever you are in the company, there are moments where you clearly see there’s a mismatch, right?

That you onboarded someone who doesn’t really fit. How do you manage those misalignments? Do you do it directly, or do you empower your leaders to do so? What are the dynamics there?

K: It depends. I’ve let many people go over the years. The idea is you want to do it quickly and gently because it’s people’s lives, their careers, and they’ve got families and mortgages.

You want to make sure that people are taken care of financially and that they have time to find their next job. You have to be respectful about it.

It depended on the manager. Some people were comfortable doing it, some weren’t. I offered many times to let people go. Sometimes they took me up on it, and sometimes they did it themselves.

But the most important thing was acting rapidly because the longer you wait when someone’s not an obvious fit, the more discontent you create internally. You lose productivity and the confidence of your team that you understand what’s really happening in your company.

P: Kathryn, I have a question on this. The mantra that you read about in startup books is to hire slow and fire fast.

But in reality, especially in the early days, this is a bit tricky because you need people fast. Perhaps you cannot make as thorough an analysis as you would like.

Moreover, if you have 10 or 20 people and you’re firing one or two, you’re actually firing 10% of the workforce, which is a lot.

And even in terms of morale, it can impact the company. What’s your take on this, and what’s your experience? Is it really true that we need to hire as slowly as possible and fire as fast as possible, or do you have a different perspective?

K: My perspective is that I’m a buyer, not a shopper. I don’t like to take a ton of time to make a decision.

I think you waste a lot of time when you’re deliberating over something. Just make a decision and then unmake it if it’s a problem. I’d much rather do the fast hire, fast fire.

Slow hiring is from a growth perspective. Don’t hire someone until you absolutely need them, but once you need someone, do it fast because it just takes so much time.

It’s like raising money; it’s such a distraction from running your business. Hiring people is the same way. If you have lots of candidates, just find somebody. Most people are probably going to be okay if they have a background that supports the job you need.

R: I have just one more question. What’s one resource that was invaluable to your success. This could be a book, a podcast, a mentor, etc.

K: Oh man. You know, there was someone who I guess you would say was a mentor.

I started doing technology work in the mid-nineties, right at the beginning of the dot-com era. A family friend was the former CEO of a large credit reporting agency, and he had a lot of great things to say that I listened to back then. He was the one who actually got me into this business, frankly.

He always leaned really hard on his leadership team and wanted them to make decisions. I would say that people on my teams have been my biggest support. Whenever I have a question or a problem, I love to talk with them about it, even if it doesn’t involve them at all. Walking around, talking to people — that’s really, really important.

One thing that I remember he said one time was, ‘Don’t be a bastard over a nickel.’ It’s just not that important to save a nickel. It’s much more important to move quickly. That was really important advice and it empowered us to move quickly because we weren’t always haggling over nickels.

R: There’s a balance there, right? Knowing how to pick your battles and sometimes it’s not that important. You can use that to empower someone or build a better communication flow or whatever the goal is.

Do you have any closing thoughts, or anything you’d like to say to an entrepreneur avidly looking for insights and knowledge on how to navigate this weird, lonely path?

K: I think what I would say is to trust yourself. You can read lots of books — I haven’t — and you can talk to lots of people — I have — but it’s really important to trust yourself. Every business is different, just like every child is different. People who have 10 children will say, ‘I parent every one of them differently because they’re different.’ Your business is the same way. It’s unique like a snowflake, so you can’t necessarily apply what worked somewhere else to your business. You have to be willing to fail and to ask questions, even if you think they’re dumb. Just ask them, because that’s the only way you’re going to get the answer.

Thank You, Kathryn…

… for taking the time to sit down and speak with me and Paolo.

The journey of Kabbage is a compelling testament to innovation, resilience, and the power of technology in transforming business finance.

Kathryn’s experiences offer a wealth of knowledge for any entrepreneur, from the initial spark of an idea to navigating the complexities of scaling a startup.

Her candid reflections on the highs and lows of her journey, coupled with practical advice on building a robust startup, are invaluable for anyone looking to make their mark in the entrepreneurial world.

I hope you have taken something away from Kathryn’s story.

Thanks for reading, and listening.