EP 118 - Kikoff - Cynthia Chen

Show Notes

Most fintech companies build products for people who already have access. Kikoff was built by someone who didn't. The question this episode forces a founder to sit with isn't about market sizing or product-market fit — it's about whether you actually understand the cost your customer pays when your product doesn't exist. That number, by the way, is a quarter million dollars over a lifetime. Cynthia Chen, co-founder and CEO of Kikoff, arrived in the United States at 17 with two suitcases, no credit, and no co-signer — and spent the next 15 years building the expertise to fix the system she had to survive.

Cynthia is the founder who served as Kikoff's sole customer service rep until the company hit Series A with 30,000 active users — and still watches customer interviews and reads app reviews today.

What this conversation reveals, underneath the unicorn milestone and the Inc. 500 recognition, is the operating philosophy that made it possible. Cynthia didn't build Kikoff by abstracting away from the customer. She built it by staying closer to them than any team member had reason to expect from a CEO. She personally took calls from customers who found her phone number. She ran Hack Weeks not as a culture perk but as a deliberate product velocity engine — with team members flying in from across the country to pair with people they wouldn't otherwise work with. The result isn't just a list of product ideas; it's a cross-functional collaboration that compounds after the week ends. The AI debt negotiator that Roland opens the episode describing — an AI that calls debt collectors on your behalf — came directly out of one of those Hack Weeks. That's not a coincidence. That's a system.

The second thread running through this episode is one that every founder scaling through 50 to 200 people will recognize: the talent management problem that appears only after you survive the early years. Kikoff's first hires came from Cynthia's network. They didn't join for promotion paths or career ladders — they joined to build something with her. When Kikoff began hiring outside that network, those new team members arrived with different expectations. The career ladder Cynthia describes building isn't an HR formality; it's a retention mechanism for the company's second cohort. And the rubric she gives her team for autonomous decision-making — if it's legal and reversible, run the test — is one of the cleanest delegation frameworks in any episode of this show.

What Roland observes repeatedly at the $1M–$50M stage is that the founders who stay closest to the customer the longest tend to build the most defensible products — not because proximity is a virtue, but because it's a compounding information advantage. The companies that abstract too early, that hand off customer feedback to a layer of product managers before the founder has developed their own intuition about what the customer actually fears, tend to build features instead of solutions. Cynthia handled customer service alone until 30,000 users. Most founders hand it off at 300. That gap shows up in product decisions for years afterward.

Key Moments
‍00:38 — Why Cynthia spent her 18th birthday researching credit cards instead of celebrating — and what that night actually built
02:23 — What it felt like to arrive in the US with two suitcases and no credit, told by the person who then built a company around fixing it
06:12 — Why being 10x better isn't a slogan for Kikoff — it's the only way to earn trust when incumbents already own the search results
08:51 — How Hack Weeks became Kikoff's primary product innovation engine, not a morale exercise
12:46 — The talent management problem that only appeared after Kikoff survived early-stage: what happens when your second cohort expects a career ladder your first cohort never asked for
15:34 — The two-question rubric Cynthia gives every team member for autonomous decision-making: is it legal, and can you reverse it?
16:13 — Why Cynthia served as the only customer service rep until Series A — and why she says the learnings from those calls shaped every product decision that followed
18:43 — How Kikoff navigates AI deployment in a heavily regulated space serving underserved consumers — and why "is this good for the consumer?" is their most effective compliance framework
21:57 — The honest state of VC funding for female founders: why the recent improvement in numbers is narrower than the headlines suggest

If you're navigating the gap between your founding team's culture and the expectations of the talent you need to hire next, Midstage Institute works directly with SaaS and software founders at the $1M–$50M stage to build the operating infrastructure that makes that transition without losing what made the company work in the first place. mdstg.ac/drag-erase.

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Kikoff is offering Scaling Without Breaking listeners 80% off their first month of any Kikoff plan. If you or someone you know is building credit from scratch — or needs to get back on track — this is the most accessible entry point they've built. Visit getkikoff.com/swb to claim the offer.

#SaaSFounders #FintechLeadership #ProductVelocity #FounderLedGrowth #ScalingWithoutBreakingMost fintech infrastructure is built to sell.
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Transcript

Roland Siebelink (00:38)
Hello, everybody, and welcome again to the show where we talk with startup leaders who are done winging it and removed the drag on their way to scale. I'm very honored, with my next guest. She came to the United States as an immigrant with no money and no credit, the kind of financial invisible that the criticism was never designed to help. She went to earn a master's in mathematics of finance from Colombia,

built risk-management systems at Capital One and Deloitte, and became a founding or executive member of three fintech companies that each reached billion-dollar valuations: OnDeck, LendingHome and Figure. But instead of staying comfortable in the executive suite, she went back to the problem that shaped her and she built Kikoff, which has now helped millions of Americans build more than 240 million credit points equivalent to raising every US adult's credit score by one point.

And just hit unicorn status herself, and just before this recording, she's been named a top female founder. And her latest bet is an AI that calls debt collectors to negotiate debt on your behalf, so you don't have to. With that, everybody, meet my guest, Cynthia Chen, the co-founder and CEO of Kikoff. Welcome to Scaling Without Breaking, Cynthia.

Cynthia (01:50)
Hi, Roland. Thank you for the amazing intro.

Roland Siebelink (01:53)
Of course, you have an amazing life to talk about, it would not be a service to our listeners to not inform them about that. Cynthia, you came to the US with no credit, went through the exact experience that Kikoff is designed to fix, and then spent 15-plus years in fintech before actually founding Kikoff. Most people who live through such a broken system, they either adapt to it or they fight it. What made you decide to build a company around fixing it?

And why now rather than when you were at Figure or at OnDeck?

Cynthia (02:23)
As you mentioned, I came to the US when I was still a minor. I was 17 years old, first-generation immigrant. When I arrived in New York City, I had no friends, no family, no money, and obviously no credit. All I had was two suitcases. When I arrived on Columbia University's campus, I was amazed by the fact that many of my American classmates were using credit cards to make everyday purchases, including books, but I was mainly using cash or later debit card. I got really intrigued by that because I grew up in a country where there was not yet a personal credit system,

Cynthia (03:10)
and started to teach myself about consumer credit. And the more I learned about it, the more I realized how difficult and expensive life would be without good credit. I obviously needed to lease my own apartment when I graduated from college because nobody would be my co-signer or guarantor on the lease. I had to buy my first car.

If I did not build credit, I wouldn't be able to achieve that.  I decided to work on it. On my 18th birthday, instead of throwing a party, I spent the entire night sitting in the computer lab of my dorm building, researching credit cards. And magically, I applied for an MBNA student credit card for Columbia students and got approved for $500 of credit line. That was the best birthday gift ever and officially marked my entry into adulthood.

As I worked for many years after college in consumer small business finance, I realized that there were more people who needed good credit than I thought.

I was working at lending companies. Every day, we would decline tens of thousands of consumers or small business owners because they did not have good credit and the number of people associated with poor credit or no credit was very high.

On average, if you had poor credit, your lifetime cost from higher interest and fees and the lack of opportunity to accumulate home equity because you couldn't get a mortgage is estimated to be a quarter million dollars.

After a pretty successful run in FinTech, I decided to found Kikoff in November 2019 because I really wanted to help millions of consumers build credit, especially those who are new to this country or who did not grow up in the most affluent families where the parents could put their children on an authorized user credit card or those who got overburdened with debt, especially student debt, who missed a few payments and then got their credit destroyed and needed to get back on track.

And I looked at the existing solutions in the market and found that they were either very expensive or not very user friendly in terms of the product design.  I decided to do something that hopefully would be 10x better.

Roland Siebelink (05:57)
I'd love to double click on that 10X that came up in a different conversation just the other day. When you look at competitive products, it's not enough to just be a little bit better. Most founders do say 10X better. Why is that in your mind?

Cynthia (06:12)
Because incumbents already had the brand awareness. They had been advertising their products for multiple years and they already occupy all the Google search results because of years of investments in SEO. For consumers to trust you enough to give you their most confidential personal information including social security number, date of birth, address, and cell phone number, you have to be better than the incumbent because you don't have the trust and brand awareness yet. Your product must be so compelling, must work so well that you can even compete with the incumbents.

One of the key reasons why we have been successful is very high product velocity. Customers have very, very high expectations and they also have lots of pain points. You need to keep innovating and introducing new products that can solve more and more pain points in their financial life in order to stay relevant.

Roland Siebelink (07:25)
Is that something you have to manage through a culture or through the people you hire? Or is that something that you task your CTO with? How do you actually establish and maintain that product velocity over time?

Cynthia (07:40)
That is a great question. High product velocity is indeed a very important element of our product philosophy and company culture. When we recruit, we tend to hire people who demonstrate strong ownership and sense of urgency. And once you have those, then product velocity tends to be higher. We also encourage people to constantly think about new and better ways of doing things. That's why we run multiple hack weeks each year  when we fly our colleagues over from other parts of the country or sometimes even other parts of the world, and they can work on any idea they have and people are very enthusiastic about them. They actually work on multiple projects on average at each Hack Week, and a lot of our new product ideas came from Hack Week projects. For example, our AI debt negotiator was the offspring of a Hack Week project.

Roland Siebelink (08:51)
Excellent. And multiple hack weeks per year. That's a serious use of resources.

Cynthia (08:57)
it is worth every dollar spent on it because we got awesome product ideas and also great for people to pair with someone that they usually don't have the chance to work with. It actually makes collaboration cross functionally better post-hack week and better collaboration usually leads to higher product velocity.

Roland Siebelink (09:20)
Of course. And I'm guessing higher employee people staying longer at the company as well.

Cynthia (09:27)
Yes, yeah, it's a huge boost to team member morale.

Roland Siebelink (09:31)
That's excellent. What made you  invest so much time? Because most companies only do  maybe two, three hackathons of one day per year, if even that. Was this something you took from one of your previous companies or did you just gradually increase the time and see it returning on investment every time?

Cynthia (09:42)
Some of my previous companies had hackathons, some didn't. And I definitely prefer those that had hackathons. And this is the first company I had worked with that had this many product lines. It is more important for us to have a hackathon culture here because we do have higher product velocity

Roland Siebelink (10:16)
You’ve been in business for quite a few years and of course you've also been through  many changes in the previous companies you worked at.  Part of that is that there's gonna be some changes in your leadership team, your executive team, and you mentioned in a prep call that that's something you're going through at the moment as well. Just in general though,  what makes you feel you want to make a change to a leadership team, when does it feel to you, okay, now it's time to make a

Cynthia (10:46)
We are in a marathon, not a sprint. This is a six-year-old company and we are just starting. There's a lot to do.

Roland Siebelink (10:51)
Right.

Cynthia (11:02)
As much as we believe in very strong work ethics, we do want to make sure that we operate in a way that is sustainable, that will make people who join the company today want to stay here for five, ten, or even 15 years. We are here to build a sustainable and generational company. In order to achieve that, we must ensure that people see a career growth program. will introduce career ladders, communicate expectations for each tier so that people

have something to work on. They have a compass that will guide them into the higher tier. Or maybe if they don't want to get to the higher tier, if they'd rather become a productive individual contributor, that's just fine too. But that expectation and giving people a path to where they want to be is very important. And we do promote internally a lot.

I think most of our senior leaders grew up with the company. We do bring in new senior talent as needed because as the company grows, we naturally just have more need for leadership. We need leaders who have scaled larger organizations before.

Otherwise, we're doing a disservice to our very talented team members.

Roland Siebelink (12:20)
Since you also just made it to unicorn status, I believe, congratulations.

Cynthia (12:29)
Thank you. Last year, it was a year ago.

Roland Siebelink (12:33)
A year ago, okay, fair enough. Five years in, that's pretty fast. I love that.

Cynthia, is it because you're growing so fast and because the requirements change so fast that sometimes a change is needed faster?

Cynthia (12:46)
Sometimes yes, because yes, we did grow very fast. When you grow fast, you may experience challenges that you did not really anticipate. When we first started, we didn't really have a very well-defined career ladder because everyone just focused on survival, product-market fit, making customers happy. Nobody really thought about the next level for themselves. When the company grew larger, we had more folks coming and they would have different expectations because they may have come from places where they were very used to a very structured career development program.

You have to meet them where they are. Your initial cohort would be people that you recruit from your network. They came here for you. They did not come here for a promotion, the next level, manager responsibilities. They came here to work with you to build alongside you and create something very special. And as you bring people from outside of a network, from a more diverse set of companies, then they will have different expectations and you have to upgrade your talent management program to make it work for most people.

We have designed a very good onboarding experience where expectations are communicated pretty early. And even before onboarding, during the interview process, sometimes we do the reverse sell. We actually tell them what it's like working here at the speed they need to move at and it helps us and also helps the candidate decide whether this is the right fit. And there are people who are not used to the speed that we move at and some of them choose to part ways early. That's all normal. think the key is that we make that message very clear to existing and prospective employees. We try to remove friction from the process and streamline decision making and empowering people with autonomy and independence. If people don't have to ask for permission every time, velocity will be higher. We do that. We have more proactive communication on expectations, what can be done or cannot be done.

I very clearly tell team members that if you want to run a test, as long as it is legal and it is reversible, you should feel free to run something. Don't break the law.  Don't break the law. And make sure that if it goes wrong, you can reverse that. As long as those two boxes are checked, it is generally  okay.

Roland Siebelink (15:34)
I love that. That's such a simple rubric for people to keep in mind.

Excellent. Okay. I love that. That's also  a shortcut to a lot more delegation, I think, which is often  challenging when you come from all the way from the founding team and now you're almost 200 people now.

I guess that was related to having been on the founding executive teams of these three startups before: OnDeck, LendingHome, and Figure. That sounds like more than luck, Cynthia. What's your secret?

Cynthia (16:13)
I would say a lot of that would have something to do with luck. Every startup that's successful had to have some kind of luck. And of course luck is never enough. It is necessary, but not sufficient. I would say the secret part would be just really focus on customers.

I single-handedly served as the only customer service person until we had reached Series A and we had 30,000 active users when we reached Series A. It was quite a grind, but I'm glad that I did it, including taking random calls from customers who just found my phone number somewhere.

I think the learnings from those early days laid a very solid foundation for our product design down the road. It would just from a lot of empathy for our customers. When you actually talk to them over the phone and you hear about their life, what are the things they're worried about, and what they are trying to achieve, you would feel a very strong connection and you would think in very different ways how you could help them.

Roland Siebelink (17:32)
Is that something you still maintain to some degree? Some companies have every executive serve as a customer service rep for a day or have them go on sales calls or stuff like that just to get everyone in touch with the customer base. Is that something you've made part of your culture?

Cynthia (17:50)
We've done that before. We've done this, what we call the kikster support. We will have our team members who are not in customer service roles learn about a particular customer service topic and process customer service tickets on that particular topic. Yes, we still do that. And me personally, I still watch customer interviews and listen to customer service calls and also I look at our app reviews a lot

Roland Siebelink (18:20)
AI of course, can speed us up a lot, but there's also still issues with it sometimes being a little bit unreliable or not always producing the same result in every circumstance. How do you deal with that in a highly regulated space such as finance?

And how do you deal with all the compliance concerns there?

Cynthia (18:43)
This is very heavily regulated space, especially when you are serving the underserved consumers who regulators really care about and want to protect.

I think it's important that you invest in compliance. We work with a number of top-notch law firms to help us stay abreast of the latest development in rules and regulations so that we will comply. We also do regular compliance training. Every team member goes through multiple training sessions each year in things like fair lending, fair and accurate credit reporting, anti-money laundering, deceptive marketing, et cetera. And it is also important to invest in the right technology to automate certain pieces of the compliance process, to make sure that we are tied with our compliance controls. And I think the rule of thumb is if you think this is something that is not good for the consumer, then don't do it is really, I think, the most effective way of being compliant. If you are always making the choice that is more pro-consumer, you are a lot more likely to be consistent with what the regulators and lawmakers would like you to do.

Roland Siebelink (20:16)
you were at risk leadership at Capital One after being at Deloitte, and then you went into startup mode. That's a fundamentally different way of managing.

What were the big learnings and what were the things you almost had to unlearn from your earlier career before being successful as ⁓ a startup executive, as a founder, co-founder?

Cynthia (20:37)
Unlearning is, startup companies, there is so much ambiguity. At larger organizations, everything is pretty well defined, or there was a previous example. You don't encounter completely new unexpected scenarios.

And you are not expected to make decisions based on very incomplete or even no information. At startups, you may not even have your customers yet. You have very limited information to base your decisions on. You have to be really comfortable making judgmental calls with little or no information.

And because of that, you just have to be really nimble and be able to iterate very quickly. Because when you make decisions based on imperfect or incomplete information, even no information, you are more likely to find out what you're doing is not right and you have to change very quickly.

Roland Siebelink (21:36)
were just the Inc 500 female founders, so congratulations, that is amazing achievement. What is the state for female founders these days in your mind? I know we can't generalize too much, but do you find it still harder? Is it different things you have to fight for than your typical male colleague?

Cynthia (21:57)
The bulk of VC funding still goes to male founders. There is some increase in the amount of money going to female founders in the past one to two years, but a lot of that was driven by the fact that there are a handful of big AI companies like Anthropic that happen to have a female founder. If you carve out those handful of AI giants, the amount of money going to female founders is even less. So yes, there is still a pretty big gap between the two genders and I certainly hope that more female entrepreneurs will be getting more financial support from venture capitalists.

Roland Siebelink (22:44)
Okay. And yeah, of course, can only support that as well as your other example, being an immigrant founder, of course, and having different backgrounds.

That at least is something that I think is still supported very heavily by the Silicon Valley already mentioned that you grew up in China, came to the US at 17 with just two suitcases. Were there particular moments in your childhood, your teenage years that predicted you would be a successful founder one day.

Cynthia (23:17)
I would say focus. I can really be hyper-focused on one thing. There was this anecdote that I heard from my mom, which I don't even have any memory of, but she said when I was two years old, or maybe at most three years old, I was reading a book at home and when a neighbor passed by he saw me and then he went out and do his things and when he came back home I was still there reading hyperfocused.

Cynthia (23:57)
That neighbor was a pretty accomplished scholar and he was so impressed because he'd never seen a child so absorbed in a book for so long. He was so excited and he went to my mom and said, wow, this kid is really, really special. She'll become someone that is going to be very successful.

Roland Siebelink (24:08)
What were your parents like? Were there particular adults in your life that really inspired you as a kid or a teenager, maybe even as a college student?

Cynthia (24:30)
I would say my mother.  I think she always encouraged me to try things that hadn't been tried by other people. The fact that I decided to apply for colleges in the United States when I was actually only 16 years old, was direct influence from my mom.

I actually skipped a year in high school. I skipped my senior year high school and went to college one year early. I didn't have a high school diploma. Sometimes I joke I'm a high school dropout. When I do things like that, my mom is always a big supporter. She never says something like, oh, this is very unlikely, or nobody has been successful with this before.

She's always like, if someone else can do it, you can do it too. And even if someone else has not done it, you can still do it. I think that was very important early learning for me. And that is still something that keeps me motivated as an entrepreneur.

Roland Siebelink (25:36)
Now you are a successful founder and an adult that may be inspiring many other younger, newer founders coming after you. What's the one piece of advice you would always give other founders in their own startup journeys?

Cynthia (25:51)
Really listen to your customers. If you can only do one thing,

I would say learning about your customers, not just about how they use your products, how they use other products, but really about what are the things that they are worried about, the things that they are spending a lot of money on, the things that they are wasting a lot of time on. I think that's important. Know who your customers are and be able to think from their perspective.

Roland Siebelink (26:24)
Very good. Cynthia, this has been an amazing interview.  Where can people find out more information about you, about your company? And is there anything in particular they should download or look up?

Cynthia (26:35)
So everyone's welcome to check out our company's website, kikoff.com.

It's K-I-K-O-F-F.com.

Without the C, just a K. K-I-K-O-F-F.com.

You will be able to see all the products that we have built. And you are more than welcome to check out our career section. We are hiring a lot. And feel free to apply for those amazing job opportunities.

Roland Siebelink (26:46)
Excellent. And if somebody wants an introduction to Cynthia and they know me already, of course, I'm happy to oblige as well. Cynthia, this has been an amazing interview. Thank you so much for your time. And once again, congratulations on making it into the Inc 500 female founders list.

Cynthia (27:17)
Thank you for having me.

Roland Siebelink (27:18)
And for the audience, thank you again to making it to the end and we'll have another not quite as amazing founder, but still a very good one next week again. Thank you for listening and stay tuned.