Parking lots: they occupy more than a quarter of urban land, and yet remain one of real estate’s most overlooked assets. With most lots still managed by pen, paper, and guesswork, millions in revenue is left untapped. Meanwhile, parking is a daily headache for most Americans—endless circling, confusing signs, and clunky payment machines.

AirGarage was born from firsthand frustration. As college students, Jonathon, Chelsea, and Scott faced the challenges of campus parking everyday. Their first idea was straightforward: connect students with nearby homeowners open to renting out their unused driveways. But, as they dug deeper, talking to property owners and surveying the landscape of underused lots, their ambitions grew. AirGarage now handles all aspects of operating parking facilities while boosting revenue for owners through technology, including dynamic pricing, license plate recognition, and online marketing .

Today, AirGarage manages over 300 locations in 38 states and has processed more than 10 million parking sessions. With a vision to bring all real estate online and AI-optimized, AirGarage is poised to transform not just parking, but the way cities and owners unlock the value of every square foot.

Here’s more about Jonathon, Chelsea, and Scott, answering Headline’s Founder Q&A.

What is your drink of choice?

Scott: Espresso.

Chelsea: Diet Coke.

Jonathan: Black coffee.

What’s on your desk right now?

Chelsea: AirGarage coffee mugs and every color pen.

Jonathon: Parking tickets.

What business question do you hate the most?

Scott: Are you going to replace your entire team with AI now?

Who was the last person you called or texted?

Scott: “My mom; it’s snowing in Texas!”

Jonathan: My best friend, Michael, from New York City.

Chelsea: “It was these two - asking where they are!”

What would your last meal be?

Chelsea: Joyride Pizza in San Francisco.

Scott: Farmhouse Thai in San Francisco.

Jonathan: Waffle House’s all-star special.

What about being a founder has most surprised you?

Chelsea: Being your own boss is just a vehicle to have lots of bosses. Customers, investors, even ourselves.

Jonathan: I appreciate the rewarding aspect of building a team and seeing them grow. I didn’t think about that when we started. For instance, it’s been awesome to see Bryan, our VP of Ops, excel and move up the ladder for six years.

What is your unofficial catchphrase?

Chelsea: If you aren’t cringing about who you were six months ago, you aren’t growing.

We sit down with Lena in Stockholm, where open banking fintech Brite Payments is being built. On a mission to equip merchants with instant payments and payouts, Brite is not only one of Europe’s fastest-growing fintech companies but also one of its few profitable ones.

An experienced payments executive, Lena started Brite in 2019 on a small angel-led seed and raised a $60M Series A from Headline and Dawn Capital in late 2023, the largest raised by a solo female founder that year. “I’m not the typical ‘go-big-or-go-home founder,” she says as she shares her version of sustainable growth, why churn is the most important metric, and why the so-called Klarna mafia used to gather around bad pasta. The interview has been edited for brevity and for clarity. Reading time: 10’

First thing: What’s something people sometimes get wrong about Brite Payments? One thing is that we aren’t part of a third-party infrastructure. In fact, we’re a fully standalone payment method running on proprietary rails – Brite receives funds, collects, and reconciles them. It’s a complete solution, ready for the merchant to plug in. With us, money instantly moves between merchants and end users – in both directions – with significant savings potential compared to incumbent payment methods, including credit cards.

Now let’s take a big step back: What’s an early learning that you carry with you to this day? To tell things as they are but in a respectful way. This is something I learned from my dad, and I believe it has taken me to where I am now. I think people know me for speaking my mind. But when someone is rude to others, especially to those they might perceive as “less important,” that’s a big red flag for me.

How does this apply to venture building? Never hire people who look down on others – whether it’s their direct reports or the office cleaning staff. In some startups, there’s a noticeable difference in how misbehavior is handled depending on a person’s role or perceived value within the company. High performers, whether they are salespeople or rockstar developers, shouldn’t get a free pass on behavior that wouldn’t be tolerated by the rest of the team. You can set high standards and demand a lot, but still treat everyone with respect. This holds particularly true for founders; you may have an inner voice telling you that things aren’t moving fast enough, or that they are not being done the way you would do them personally, but especially as the business grows you need to appreciate that others don’t think the same way as you do. Back to workplace behavior, nobody should ever leave a meeting feeling bad about themselves.

Since you mention the workplace: What’s an object you keep in your office to remind you of who you are? I have a ton of photos of my friends and their families. I work long hours, and I like it. As long as you still make time to spend with family and friends, it doesn’t have to become emotionally draining or a downward slope. I aim to speak with friends and family before and after work every day, bookending what can be very long work days. As a founder, there’s a risk of ending up in a “me and my problems” mindset, but speaking with people outside the business gives you perspective and helps keep you grounded.

Another thing I have on my desk is some of my very first business cards from my time at Klarna. Now, the branding isn’t nearly as slick as it is today, but it’s a reminder of where my journey in fintech started.

“When Klarna closed the $155M investment round in 2011, there was so much work to do that I went to the office on a Thursday morning and came home on Saturday at 5 AM. And I loved it.”

Let’s get to Klarna! You were there super early and with the company for almost 7 years. How did it start? I ended up in Stockholm by chance! I was wrapping up my Master’s Degree and working on a thesis with quantitative data collection among a cluster of Stockholm’s science and tech companies. Klarna, at that time, was still a very Swedish company, doing online invoices, and looking to grow both geographically and in terms of the product offering. Like most Business School students back then, I had dreams of McKinsey or Goldman Sachs. When they approached me, I entered the interview more interested in getting interview experience than a job offer. My interview was with Sebastian Siemiatkowski, Klarna’s founder. He was incredibly compelling, so I wanted to give Klarna a try and accepted. Then everything happened so fast. There was so much to do as Klarna was internationalising. Six months in I was promoted, and from there it was a wild entrepreneurial ride. When we closed the $155M investment round in 2011, there was so much work to do that I went to the office on a Thursday morning and came home on Saturday at 5 AM. And I loved it.

What’s your fondest memory of that time? The teamwork. Everybody really wanted to make it work and they cared. Even though things could get messy as the company grew, the early days had no politics. Everyone had a very “how can I help” attitude. Everyone would do a bit of everything. I was running around projects, Operations, PR, sales, and marketing. Brite’s COO, Alexander Kassai, was also at Klarna back then, and we must have had hundreds of vending machine dinners; really boring pasta with tomato sauce. The so-called “Klarna Mafia” formed around that bad vending machine pasta.

When did you know it was time to go? When I started feeling, “I’ve done this already, I already know how this works.” When Klarna acquired the German direct payments company Sofort, I saw that the company was loved by consumers and wildly successful with a high-margin but fairly basic product. It was my first exposure to account-to-account (A2A) payments. However, I received an offer to join a financial services company as Chief Product Officer. Having experienced sales and marketing at Klarna, I wanted to be on the other side and experience product development. Making that decision was very difficult and emotional, as I felt a great deal of loyalty towards Klarna. Just a few months in, I was CEO of the new company, which was eventually listed on the Stockholm Stock Exchange.

And from there? Eventually, I started thinking: Why is there no instant payments product that combines a strong consumer brand and an easy-to-use product with a state-of-the-art platform and a compelling business proposition for merchants? Something that decreases the cost of payments for merchants overall, as well as taking away the credit and fraud risk. The idea of Brite Payments started forming. The turning point was talking with a friend about the account-to-account space. We agreed that the opportunity was massive, but disagreed on how it should be tackled. I started arguing that it should be done in a certain way, and the more we spoke, the more I realized I already had a plan of sorts. A plan for what became Brite Payments.

“I’m not the typical “go big or go home” founder. I have always had a big vision for Brite Payments but wanted to do things at our own pace and reach profitability as fast as possible.”

You are a first-time founder. Was it what you were expecting? I was mentally prepared for choppy waters and plenty of ups and downs. What I wasn’t prepared for were the sleepless nights in the early days. I was accustomed to getting little sleep because I had too much to do, but it was a new experience to wake up at four in the morning thinking, “This can actually go south and not succeed.” I started speaking with other founders and then realized this was completely normal. And it really is normal, in the early days of a business, to endure a lot of mental pressure. It gets better.

Tell me about the time it got worse. What was the toughest moment? When we had just launched our product, there was a time during which a competitor started going after our early customers really aggressively. They managed to take some large clients from us. We were at the point of almost breaking even, and all of a sudden, we were back to burning money and having to look carefully at our runway. It was like hitting a wall. Eventually, however, you rationalize and begin to see the value in greater diversification.

Sounds like a blessing in disguise... Some of our initial customers were quite international. This led us to open lots of markets quickly. We launched in Sweden, Finland, and the Netherlands in quick succession. We had no choice but to go where the customers wanted to go. Although this rapid expansion was costly, it got us thinking beyond the relatively small domestic Swedish market very early on.

“Sure, money can buy growth at all costs, but at a certain point, you start overpaying. You can spend a ton on marginal improvements and revenue that doesn’t stick. We don’t seek that.”

Your fundraising story stands out. You founded Brite in 2019, raised a small angel-led Seed, doubled profitability in 2022, and raised a $60M Series A from us and Dawn Capital in 2023. Why? I’m not the typical “go big or go home” founder. I have always had a big vision for Brite Payments, however I wanted to do things at our own pace, with the goal of reaching profitability as fast as possible. Seeing some of our peers raise significant rounds in early 2022 did make me question this growth strategy though. I wondered, are we scaling fast enough? But the market dynamics then shifted, and we’ve seen some of those companies that expanded very quickly needing to lay off staff and scrap expansion plans. It was the perfect time for us, however, to fundraise and use the strong foundations we had laid to move faster. But we won’t ever think in terms of spend, only of investment and growth. If we aren’t as fast as we should be, we’re not going to be spending as much. To some extent, we’re front-loading the investment. We are building a lasting business, and while we cannot preempt market developments, we want to stay in the sweet spot where we only tap into the side of the market that is sustainable for us to address long term. Sure, money can buy growth at all costs, but at a certain point, you start overpaying. You can spend a ton on marginal improvements and revenue that doesn’t stick. We don’t seek that.

How did you choose your cap table? We optimized for people, not for brands. Of course, the immediate question was: Does this fund have a good reputation? How large is the fund? Where are they in the fund lifecycle? From there, we thought about the individual investors. Conversations with fellow founders confirmed a universal truth: Money is interchangeable, but the real differentiator is the people you choose to work with. The question then changed to: Who are you likely to have a good relationship with? Who understands your vision? Of course, everyone promised “value ad,” but I didn’t necessarily think we’d receive help and introductions. The fact that it has happened is something I have not taken for granted.

What’s the most important company metric? Boring answer, but it’s churn. It’s a good metric to see how good your product and company really are. Brite Payments has really low churn on both the merchant and the consumer side. Our business is reaching the age in which we can really appreciate it: When your company is one year old, customers that were onboarded three months ago don’t tend to churn yet. While some companies might be very focused on top-line growth and payment volumes, or transaction margins, I believe that churn paints a clearer picture.

“We treat trial or probation periods as actual test periods to get a real sense of the collaboration. If a team member continues past their trial period, it’s usually the start of a long tenure at Brite Payments.”

The churn among Brite Payments employees is also quite low, especially for a fintech. How have you achieved this? Firstly, we treat trial or probation periods as actual test periods to get a real sense of the collaboration. If a team member continues past their trial period, it’s usually the start of a long tenure at Brite Payments.

Secondly – and this is common in fast-growth startups – people can stay in the same role as the company grows while the nature of the role changes completely. For example, imagine running accounting in a 20-person startup in 2020. Two years later, the company might have 200 employees – same job title, but the job has gotten so many times bigger. With Brite Payments, we’ve tried to hire a lot of experienced and senior professionals who are still flexible – helping us to grow a team of leaders that are the right fit whether we have a headcount of 20 or 200. This has made sustainable growth so much easier.

How do you tackle the quasi-monopoly of Visa and Mastercard? First off, a lot of merchants don’t love card payments. They have to offer them because it’s the standard that everyone expects. But they aren’t reluctant to decrease the proportion of credit card payments. They are expensive, they are not that fast, and they aren’t that convenient in handling returns and preventing fraud. Secondly, we are getting to a point with our proprietary instant payment network – Brite IPN – where we cover enough markets to make us a suitable option to cover all the local needs of the largest merchants. Thirdly, the convenience of online banking apps is significantly improving, making non-card payments more attractive. Outdated methods like the scratch cards used by some banks are becoming obsolete, replaced by seamless mobile app integrations. The stars are aligning; market awareness is growing, consumer expectations are increasing, and Brite Payments technology is built on what’s going to be the next payment standard.

Are you building a startup that resonates with these themes? Feel free to reach out directly to our General Partner Jonathon Userovici here.

Growing up with more than 15 cats and dogs running around at any given time, Brandon Werber affectionately calls his childhood home the “Dr. Dolittle House.” “We even had a couple of rats, too,” he laughed. “Nala and Ace Ventura. We absolutely loved them.”

His father took in most of the animals after they were left at his veterinarian clinic. As a child, Brandon watched his dad dedicate himself to his profession. It instilled in him a strong love of animals and desire to improve their lives.

Brandon followed in his dad’s footsteps, not by becoming a vet but by working to expand access to quality pet healthcare through his startup, Airvet. He launched the company in 2018 to offer pet parents a stress-free, virtual option to connect with a licensed veterinarian 24/7. Now, Airvet caters to enterprises who want to provide pet telehealth as a benefit to their employees, embracing the future of work to include family in all its forms. Airvet is today one of the largest animal telemedicine companies in the country - more than 250,000 pet parents have used Airvet’s services and over 3,000 petcare providers have partnered with the platform since its founding.

Airvet is addressing a serious vet shortage at the same time that pet ownership is reaching record highs. More than 70% of US households have a pet, meaning the ubiquitous nature of pet ownership along with the evolving definition of family has created a pressing need for employers to reconsider how they are defining and broadening their approach to wellness and family benefits.

After investing in Airvet’s Series A in 2020, Headline recently doubled down on its support for the company by participating in the $18.2M Series B. We caught up with Brandon to discuss his journey as an entrepreneur, his mission to revolutionize petcare, and why today, more companies are recognizing the pets behind the workforce and adding Airvet as an employee benefit.

Sounds like you had a pretty unconventional upbringing. How did your experiences as a kid inspire you to found Airvet?

It was unconventional in every sense of the word, that’s for sure. I’d come home from school and a herd of animals would be waiting to greet me. I loved it. For a time, I wanted to become a vet, too—I worked at my dad’s clinic every summer, hoping one day I could save animals just like him.

But I soon realized that most people don’t have the luxury of having a vet for a parent. I can just swing by my dad’s place for a quick check-up if my dog is feeling sick, but most people have to do research themselves, wait in long lines, fill out paperwork, pay for an ER visit, and more. Because of backlogs, some animal hospitals are even forced to decline service when it comes to non-life threatening emergencies. It’s incredibly stressful.

Becoming a vet might’ve been my goal originally, but as I learned more about the industry, I thought, “Why help 50 pets a day if I could help 50,000?”

What was the eureka moment that inspired you to launch Airvet?

I decided to launch Airvet following a stressful experience I had with my little Frenchie, Carlos. He was sniffing around our backyard and ate pieces of an Asparagus Fern—a plant that’s toxic for dogs. He started vomiting profusely. At the time, my dad was out of the country so I had no way of contacting him.

I was in panic mode. I didn’t know if the situation was life-threatening, if I could handle it at home, or if it was going to cost $5,000 to go to an ER.

Your pets are family. When they’re sick, you’re scared. And if you can’t help them, it’s the worst feeling ever. This was the first time I felt that kind of fear—my eureka moment. But I know that for many pet parents, this happens more often than it should.

Around this time, digital transformation in healthcare was starting to pick up, and the experience inspired me to explore the potential of telemedicine for pets. With just one click, pet parents can hop on a call with some of the best veterinarians in the country. And by using an affordable platform like Airvet, people won’t have to choose between investing in their pet’s health, paying off student debt, or going on a family vacation. Airvet was created to save pet parents valuable time and money while also helping them access top-notch veterinary care.

Airvet’s growth is impressive. Looking back, what do you think contributed most to your success?

It’s all thanks to my team. I was a solo founder, but if I could do it all over again, I would’ve invested even more time into building my “crew,” as I like to call it. Without someone to bounce ideas off of and share the inevitable burdens with, building a company can get difficult, and lonely. Sometimes you start to question yourself.

Now that my team is as strong as ever, it’s a totally different experience. It’s not just about delegating responsibilities, although that helps with productivity. It’s the fact that my teammates truly believe in the company’s founding purpose—and they’re invested in the mission just as much as I am. We’re in it together. With them, I feel bulletproof.

More than ever, employers believe in Airvet too. What makes access to telehealth a valuable benefit for pet parents?

Pets are important family members in the vast majority of households. Companies need to take that into account when considering new benefits for employees and their families.

There’s no question that benefits offering easy access to pet care will bolster employee mental health in the long run. It’s also a fact that pets, in general, improve symptoms of anxiety and depression in their owners. If companies want a productive and happy workforce, they should be investing in the health of their employees’ pets, too.

What’s on the horizon?

We’re here to fulfill an unmet need. Animal hospitals are understaffed, vets are overworked, and pets require fundamental healthcare that shouldn’t come with an atrocious price tag. Our goal is to provide affordable, accessible care for pets of every kind.

In the near future, we want Airvet to become the go-to online destination for all things pet health. Whether that’s picking up medication, scheduling virtual visits, looking at lab results, or even connecting with other pet parents in the Airvet community, we want people to rely on us for support in critical circumstances. This new capital enables us to invest in scaling and expanding our service offerings within and beyond telehealth, to help us become a single solution for enterprise-grade pet services.

Photo credit: Emily Dulla

A mention of adult diapers doesn’t usually sizzle on a first date. But for Bianca Padilla and Jonathan Magolnick, the topic sent sparks flying.

“I remember I was like, ‘Mom, I met the person I’m going to marry—and if he doesn’t want to marry me, at least he brought me a billion dollar idea,’” she said.

Bianca said her now-husband was, in fact, a little bashful bringing up his idea for an adult diaper subscription service while they sat together at a Miami Heat game. Little did he know, Bianca and her mother had recently become first-time caregivers for her grandmother, so the concept immediately hit home.

Soon enough, Bianca and Jonathan were laying both wedding and business plans. In 2017, the husband-and-wife team founded Carewell, a curated e-commerce platform of elder care products at competitive prices. As CEO and COO, they’re on a mission to be the most trusted resource for family caregivers, and are part of the fast-growing elder care services market, expected to grow to $1.7T in the next four years.

We caught up with Bianca and Jonathan to learn more about how they’ve grown their business alongside their relationship, and how they’re changing the conversation about old age.

It’s rare to become a couple and co-founders at the same time. What are some ways that’s influenced your partnership?

BIANCA: It’s funny, most people don’t even talk about finances until after they’re married and we were talking about them three months into our relationship. That’s one of the great parts of starting a business with your partner: Especially when you’re bootstrapping a business like we did, you’re using someone’s savings, or taking out a loan or working a second job. Discussing both personal finances as well as the business finances early helps you set boundaries and guidelines.

JONATHAN: Our relationship definitely came first, but as our relationship continued to strengthen, so did Carewell. The foundations of a strong relationship and building a source of support for caregivers are the same. They’re built on trust, care, compassion, and empathy.

BIANCA: We care for our caregivers in the same way that we care for our own families. I got to meet Jonathan’s family and he got to meet mine. Those are the people who we were thinking about when we built this service. Jon and I were the first customer care agents and we spoke to our customers and they spoke to us like family members. They felt that trust, they felt that care and that compassion and empathy come through.

What’s your secret to getting through the tough moments in your relationship?

BIANCA: We both work with an executive coach and one thing we’ve learned to identify is how we behave when we’re afraid. Everyone has a different fear response, but there are patterns: some people point fingers, some people become angry, some people will lie. It’s almost more important that you can recognize these behaviors in yourself. Because once you express that you’re fearful, it’s much easier to deal with the problem or challenge. It allows us to diffuse the situation and talk through it without so much emotion.

When Jon is afraid he tends to shut down—he doesn’t speak. I’m like, ‘I just want to hear your opinion!’ but I know he doesn’t like to talk in those moments.

JONATHAN: To the contrary, Bianca kicks into a new gear, working extra hard and way too long. I’ll have to say, ‘Hey you need to take a break! Slow down, and let’s do this together.’

How does your at-home dynamic compare to your at-work dynamic?

BIANCA: I have visions of how I want to structure the culture of the business, the vision for the company and where we’re going. Jon is more of an execution type role and really supporting me getting big picture things done by handling the day to day. I’d say that that’s the case also in life.

JONATHAN: I’m more like the laundry and dishes person.

BIANCA: It’s always a partnership: I continue building the path forward and he’s the one who’s laying the tracks behind. So we work in tandem to do that and make sure that we’re both happy, we’re both successful and we’re both on the same path.

What is your vision for Carewell today—what is the opportunity you’re seeing in the market that you’re driving towards?

BIANCA: Our hope is to really usher in a new era of innovation and a new mentality around what it means to age. This generation that’s about to age is really different. They feel younger and they are in better health and they are more excited by retirement and the opportunities post work life. The industry has to evolve to keep up with them, from the way we speak to the aging population to the way products are designed.

JONATHAN: There’s such a lack of creativity happening in this space, and this is a generation that we owe so much to. Our generation will be the ones who step up.

After talking to so many caregivers, what kinds of innovation do you think we need to see in elder care? What does this new experience of aging look like for your parents, for yourselves—for all of us?

BIANCA: 90% of Americans want to stay at home rather than move to a nursing home. They want to stay close to their families and friends. But only 2% of American homes are outfitted to age in place safely. And they need products that are more innovative in terms of the way that they look: Nobody wants to fill their homes with hospital-grade wheelchairs or grab bars or toilet seats. People want things that look beautiful and that look comfortable and that have dignity to them. And so I think there’s a massive opportunity. This is why I’m always so excited about our businesses and helping curate these new and innovative products.

We love supporting visionary duos of all kinds. Check out our conversations with Honeycomb co-founders Charity Majors and Christine Yen, and Trellis co-founders Nicole Clark and Alon Schwartz for more insights into thriving partnerships.

We met up with co-founders Charity Majors and Christine Yen at the Orbit Room, a classic bar in the Lower Haight area of San Francisco. It’s where the pair has made important decisions about their company, Honeycomb.

The two engineers came up with the idea for Honeycomb — which helps developers more deeply understand the software systems they’re building — while working at backend start-up Parse (acq. By Facebook in 2013). Charity worked on the ops side, and Christine on dev.

They both realized that as more software companies move fully online, the job of sifting through massive amounts of data is no longer one that a team of engineers can do alone. With Honeycomb, they created a fast and flexible tool that engineering teams can use to get full observability of their systems, better predict potential issues, and debug code.

Let’s set the scene – we’re here on the corner of Laguna and Market in San Francisco. Can you tell us about this neighborhood? What does it mean to you guys and the Honeycomb story?

Charity: This neighborhood is where we both live, and it’s the best neighborhood in SF. The Orbit Room is where many early interviews took place and important company decisions were made.

Christine: We’ve had so many different offices over the years that none really hold outsized significance for us. Orbit Room, on the other hand, has been a constant—and some conversations are better had over a drink, instead of under fluorescent lighting.

How did you two meet? What advice would you give to yourselves back then?

Charity: We met at Parse, where we were both engineers.

Christine: Charity was the first infrastructure engineer at Parse, while I was a software engineer working on the analytics product—and while we were friendly, the early interactions I remember were all situations where some code I wrote resulted in problems in the reliability and stability of systems she had to operate.

If you weren’t working in tech, you would be…

Charity: Probably a philosopher.

Christine: Something with special effects in the movie industry. Or practical effects. I don’t really know—but I love the idea of bringing imaginary worlds to life.

What is your favorite memory of this business?

Charity: Watching people get promoted on the basis of the work they have done introducing Honeycomb, to their org, because of the outsized impact it had on the entire team.

Christine: What she said. A couple months ago, I went through a years-old deck to snag some slides with customer quotes on them—and I realized that each of the 4-5 customer references had a new title (but at the same company!) on LinkedIn. We always talk about partnering with and growing with our customers—and it was a visceral jolt of pride to see it reflected in such a simple, tangible way.

If you were to write a book tomorrow, what would it be about?

Charity: Well, observability, obviously. :)

Christine: Oh, man. If I had the time to write a book tomorrow, I would not spend that time writing a book.

Santa Monica-based Trellis has created an AI-powered research and analytics platform to make state court trial data accessible for the first time. Headline led Trellis’ Series A, announced October 2021.

There are plants in every corner: fern and palm varieties erupting out of their pots; thick, leafy vines climb the walls. There’s also a Guiana Chestnut — better known by its colloquial name, “money tree” — in their office garden. The tree is the subject of a running joke among the team, explains co-founder and CEO Nicole Clark: it represents growth in good times and is laughingly referred to as the financial backup plan during times of strain.

Together, Alon and Nicole tend to the growth of Trellis, an AI-based state court data analytics platform, with the care of gardeners. Even their own working relationship is the subject of thoughtful cultivation.

We caught up with Nicole and Alon for a stroll around their office neighborhood in Santa Monica to learn more about just what it is that makes their partnership, their business, and of course, their gardens — grow.

Let’s start at the beginning. You two seem like you’ve been friends forever — when did you first hit it off?

Nicole: Actually, my executive coach played matchmaker! She had also been Alon’s employee at one of his prior companies, and thought the two of us should meet. Obviously, she was right!

And the connection was...instant?

Alon: To me, it was immediately obvious. Nicole just has it. She has what it takes to be an incredible CEO. I’m not sure she even fully realizes it yet, but she has it.

Nicole: Alon originally joined me as a technical advisor to the company, but he was adding incredible value from the start, he was actually doing work. Most advisors just opine, which is great assuming they are smart and skilled, but leaves early founders with a lot of great advice and no one to help execute. Alon got his hands dirty immediately. I secretly knew I was recruiting him the entire time he was advising the company...I just kept integrating him more and more into the team and aligning with him on goals and strategy.

Why did it take you time to join as a co-founder?

Alon: Well, my previous company hadn’t ended well. I had promised myself that that was my last startup. Four startups is enough! Being a startup uncle (a.k.a. an advisor) was more appealing at the time — you get to come in and have fun, help the team learn and grow, and then leave all the difficult gut wrenching parts to the parents! But, at the end of the day, I’m a builder — not a consultant.

What strength would you most like to steal from each other?

Alon: Nicole is an outstanding salesperson. I am direct, sometimes abrasive. Nicole is the opposite, extremely poised and disarming. She has the power to get people excited: our team, our customers. People want to join her.

Nicole: Alon has been on every side of the table, CEO, CTO, investor, coach. It’s given him the ability to see various perspectives at once, and still prioritize. He is a master translator — he can make incredibly complex technical issues really simple and clear.

Where’s the line between your strengths?

Nicole: I have a million thoughts running at the same time, constantly switching contexts. Alon listens, brings me back to tackle one problem at a time, then actually executes — fixes it, whether it’s pushing the team, doing it himself, or in some cases pushing me. Alon is an excellent leader, and excels at driving progress. When he can’t push, he literally pulls us forward. But he gets it done. Every partnership needs that kind of balance.

Alon: I can put this simply: Nicole is like a kite — I’m the string.

The worst VC question of all time?

Nicole: What happens if Google gets into your space? You could say that to any company — large or small, corporation or startup. It’s basically a lazy VC question, it’s what investors ask when they have not dug in enough to ask relevant questions, or they simply don’t really understand your market or your business.

Alon: Without a doubt! There’s no answer to that question that will satisfy any investor. If you mention the potential for an acquisition, they get concerned the exit will be too early, too small. To quote Hamilton, “We will fight the fight and win the war.” What else is there to do?

What’s your motto?

Alon: “It’s not who’s going to let me, it’s who’s going to stop me!“ When I was very young, I found myself waiting for permission — I’ve quickly learned that I just need to do what needs to be done, even if the result is not guaranteed.

Nicole: “Life unfolds in proportion to your courage.”

You both have kids — what’s the essential routine, ritual, or question that keeps you grounded at home?

Alon: Tell my kids I love them at least once per day. You can’t say it enough. Yeah, also give them long, strong hugs.

Nicole: Bedtime!

Any brilliant advice for other Founders with families?

Alon: It’s not about quality time, quantity matters. When they grow, no one will remember you being at or missing an event, but the repeated memory of you reading them a book, listening to them telling you about their day, inventing a story, will stay with them. Some of it, I’ve learned later, but it’s never too late.

Nicole: In some ways I think the idea of attaining work life balance (particularly as a founder) is a bit of a trap. That doesn’t mean you ignore your family, it means, you should strive to be present wherever you are, at any given moment. And when you find those quiet moments with your family, at the end of the day, or in the morning, be there with them, be connected.

What’s next?

Alon: The first stage has been depleted and now we have this super booster in the second phase of the growth of the company. I told Nicole the other day, our tanks are full of jet fuel and now it’s time for us to go and execute in the fastest and most aggressive way that we can —there’s so much to do. The path is clear and strategy is sound.

Nicole: Really, this next phase of life is about growth in all ways — Trellis’ growth as a business, our team’s growth as professionals, and my personal growth as a leader, a parent, a partner and a human.

We covered Julie’s story from her upbringing in Indiana to her job as a riveter on the GM assembly line, then through the twists and turns that led her to start The RealReal.

We fell in love with the business – and Julie’s fearless attitude – immediately. Customers were absolutely obsessed with what Julie was building, and we wanted in. We’ve been with them since they were $100K in revenue, as their first VC investors. Today, the business is valued over $2B (NASDAQ: REAL).

Ok, let’s start at the beginning. You grew up in the countryside of Indiana – what was that like? How did it shape you?

We would go-kart, waterski, go fishing! It was very idyllic, but no one expected me to stay. My high school boyfriend’s dad told him, “Don’t get too serious with her: She won’t be sticking around.” I did well in school but never made it to the top of my class because I got Cs in Home Economics and Typing. I kept thinking: When will I ever have to type in my life? (laughs)

And your parents were artists, right? Does their creativity influence you today?

My parents met at the Art Institute of Chicago: they were commercial artists. My mom dropped out of school to marry my dad and didn’t end up working. My dad did packaging design for consumer goods and loved it. He’d come home, show us his work, and tell us about the problems they were trying to solve. It was an early crash course in consumer marketing. I loved it!

What did you think you wanted to be when you grew up?

I actually started out thinking I wanted to become a pharmaceutical developer! But during school, I spent a summer working at my fiancé’s dad’s plant – General Motors plant – as a Riveter. I put myself through college by riveting bumpers for the Chevrolet Monte Carlo. I literally sat on an assembly line all summer!

And you decided not to pursue a career as a riveter, apparently...

Well, first of all, I called off the engagement. I was too young! I felt my life would only get smaller with him. But doing his homework and learning from his dad made me realize how much I truly loved business. I changed my academic major from Pharmaceuticals to Business.

So, from the GM assembly line to selling software in London in the 80s. Explain!

I was 26 and I had spent the previous year and a half as a brand manager for Clorox. At Clorox, I realized all the people above me were older white men. I didn’t look like them, and I didn’t want to become one of them! It’s important to want to be the person above you.

So when I had the chance to join the productivity software industry, I took it. At the time, Software Publishing Corporation (SPC) was only at $4M in revenue. My manager at Clorox told me that he could raise the price of bleach by one penny and make more revenue than their entire company. By the way, he said all of this to me while I was standing in his office that had one of those buttons on his desk that could lock me in. It wasn’t a sexual thing...it was a power thing! Anyway, I was too young to care about revenue. I said: Okay and left.

What stood out to you as a 26-year-old woman working in Europe at the time?

I was a 5’3 (160 cm) woman in her 20s selling this whole new idea of personal computer software. So many stories! In Milan, I found myself in a 40 seat boardroom with 20 men. When they saw me, they all got up to move to the opposite side of the table. I asked why, and the best English speaker among them replied, “If we have to do business with a woman, we prefer to look at her.” So, I took a seat.

You moved back to the US...then what?

Well, years later, I joined this very promising startup. Pets.com (laughs). I got beaten up badly: Everybody knows about this spectacular failure. But let me add: The very morning Pets.com was to shut down, my then-husband asked to divorce me. I remember rolling over like, “Of course, you do!” Everything about the situation was bad. The press would be showing up at my doorstep. They’d follow my car. Wait for me outside the hairdresser. Close to 2200 companies collapsed in the dot-com bubble, but Pets.com was an easy target.

Companies obviously fail all the time – and tons more failed in the .com burst. So, why do you think Pets.com was such a point of focus for people?

People understood what we were doing. We had that sock puppet. I was always on television as one of the few female CEOs. We were an easy target. I felt like I had a public label of failure, that I was walking around with a big “F” on my chest. But once I got over it, I had no more fear. I was still there! And, I would never be afraid of public failure again.

It was about 10 years between all of this and The RealReal – how did you spend the time?

Oh it was my Odyssey. At one point a recruiter told me I was washed up. He was right! I am a woman. I am over 40. I have Pets.com haunting me. Even if I didn’t feel represented by it, I treated it as valid info. But I called bullshit. I was too young and had too much going for me! That’s when I decided to start my own company. I was at the bottom, and I came back. I was right.

Remind me, where did the idea for The RealReal come from?

I looked at Amazon for things they were bad at, like luxury. And those with a low entry barrier, like beauty. I made a large TAM, low-Amazon matrix! Then, I was shopping with a friend who went into a boutique and bought consignment instead of full price, I was shocked. She was like, “I got them at a really good price. Who cares if they are pre-owned?” But, She was adamant about not shopping on eBay. She didn’t want to risk getting fakes, nor have to haggle. I thought, “If she’ll do it in the right environment, anyone will.”

But after Pets.com you swore off of ecommerce businesses. What changed?

Within six weeks, I knew the total addressable market and I had tried every consignment platform. I knew it was it. After Pets.com, I had sworn: no more e-commerce marketplaces. But it had gotten so much easier to get a website up and test the concept.

This time, we were deliberately slow in fundraising: Only a few angels to start with. We knew it was a weird concept and wanted to work out the issues. Headline became our first VC, through Mathias, nine months later. And you were with us all the way to the $1.5B IPO.

What’s next for you?

I built a scholarship program for women with a STEM background going into business at Purdue. One at Parsons, for sustainable fashion. I push the San Francisco Art Institute to have at least 50% female students. Arts – and supporting women – are really important in shaping the future.

Daniela Binatti (CTO) and Ricardo Josuá (CEO) are co-founders Pismo, headquartered in São-Paulo, Brazil.

The two started the company together with Juliana Motta and Marcelo Parise – Daniela’s husband, after Daniela lured Ricardo out of retirement. From the earliest days when we first met Daniela and Ricardo in Sao Paulo, we saw the potential for Pismo to change the way banks run- in Brazil and beyond. And they did. After leading their Seed round in 2016 from Redpoint eventures (now known as Headline Brazil), Headline went on to lead their Series A through the US Early Stage fund and helped them expand into the American market. Headline continued to support Pismo in its Series B with an investment from our Global Growth Fund. Get to know Daniela & Ricardo in this interview.

What is the #1 trait the four of you share as cofounders?

Ricardo: This might not come across as a compliment, but… We all worry a lot! We don’t take things lightly. We are anxious about everything. True control freaks. But we are also extremely resilient.

What’s the most overrated founder trait?

Ricardo: Genius. People like to imagine entrepreneurship happens in giant leaps. Cue movie montage where people see algorithms solving themselves in front of their eyes. Reality: You need good intuition, but it’s how you implement and execute that makes all the difference. Great ideas are always an iterative process. No successful founder hasn’t ended up doing more than they think they could do. 20/20 hindsight is a form of vanity.

Daniela: From the outside, everything looks like an overnight success. The cult of personality is one of the tackiest aspects of the tech business. You create your story while you still struggle with daily things like everyone else. Success is always a joint effort. It’s circumstantial and based on the right time and people.

When did you know you would work together?

Daniela: We met in 1999. A life together! Ricardo was co-founder of Conductor, the company where I worked as infrastructure and technology director. When the company was successfully sold, Ricardo sort of retreated to the countryside. I stayed longer. But when I realized I wasn’t spending enough time with my daughters (then 7 and 5), I took a break. Visiting Silicon Valley, I saw the gap between the services their companies were building and Brazil’s own financial infrastructure. I saw the opportunity. I called Ricardo: I wanted him out of retirement!

At first, he didn’t seem interested. I kept insisting. Then we spent 7-8 months planning together. He’s one of the most intelligent people I have ever met and the only person I wanted as CEO of our company. He’s like a brother to me.

Pismo has four co-founders. Two of them husband and wife. How do you handle disagreements?

Ricardo: We have shy of 160 people working at Pismo. Dani and I still do every single new employee onboarding. And we tell them what we learned working as co-founders: You might see us fight with each other. Or vent about one another. Treat it as a sign of respect. There is no long-term resentment, no emotional grudges.

Daniela: I am the head of Engineering, and my husband, Marcelo, is our CTO. When the four of us fight, Marcelo and I are rarely on the same side. But we cannot imagine not working together.

Why did you name your company after a beach in California?

Daniela: In 2014, Marcelo and I were traveling in California. The podcast I was listening through mentioned how a company’s name didn’t need to have a meaning. It needed to be short and easy. We were driving from San Francisco to L.A. and saw this huge billboard: Pismo Beach. We told ourselves: We’ll name our company after it. And buy a house there if things work out.

Ricardo: Yes - in the event of a Pismo IPO, the original plan was to buy a shared house there. But I thought the communal kitchen was one step too much, after spending all this time together! So we settled on getting tattoos together with the Pismo logo. I deeply regret agreeing to that!

How did you convince the most important financial institution of the Southern Hemisphere to move core processing and payments on your cloud?

Ricardo: At the time it sounded preposterous even to me! No way they would listen to us. But they did. Dani and I tried to be as humble – we were like small kids to them. We told them we could help them run more efficiently. What impressed them was how fast we could execute. Now the inertia is on our side: we have been adding more than 2M new accounts every month!

Headline was the one inviting us to look at enterprise sales when Pismo was only 10 people strong. They pushed us to do it, to see what happens. They connected us to the right coaches. They made us intros and scheduled meetings for us. It became a huge part of what we are today.

Fill in the blanks. Because of Pismo, you will never ___ again.

Ricardo: It’s going to sound corny, but I’ll never dream small. Our previous company was successful: It now employs thousands of employees. But with Pismo, I’m having conversations with large banks in the U.S, in India, in Singapore. We would have never thought these things would be within the realm of reasonable for a company starting out of São Paulo.

Daniela: I’ll not feel intimidated in starting a company. I have struggled with impostor syndrome my all life. As a woman, I always have to remind myself I am not less than others.

My parents were from the countryside. They were schooled until they were nine years old. My dad often relied on the help of others to put bread on our table. When I was 14, my mom put me in a computer course. I was in love. Later, I didn’t have money to pay for my University. So, I started working as an intern for Brazil’s department of traffic. I assisted the guards with their fines. Every December 24, I would hold traffic stop signs in front of the shopping center. It was difficult for me. My parents still don’t have any idea of the scale of what we have built with Pismo! When I asked my mom how much Pismo was worth, she guessed 50.000 reals ($9500). I said: A little bit more!

Ricardo: She made it 100% against all odds. People would often discourage her. But she is so tenacious. She was with me, in convincing me to start Pismo. I tried hard to dissuade her, telling her how hard pulling this off would be. But she is tenacious. And she built a deep tech company on cutting-edge technology, something that was never developed before. She went to public school, and her daughters can now attend one of the best schools in São Paulo.