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Carewell’s Cofounders on Love, Marriage and Growing Old

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.

Meet the Headliner: The husband-and-wife team founded Carewell, a curated e-commerce platform of elder care products at competitive prices. 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. Headline caught up with them to learn more about how they’ve grown their business alongside their relationship, and how they’re changing the conversation about old age.

Bianca Padilla & Jonathan Magolnick, co-founders of Carewell | Headline

The husband-and-wife team founded Carewell, a curated e-commerce platform of elder care products at competitive prices. 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. Headline caught up with them to learn more about how they’ve grown their business alongside their relationship, and how they’re changing the conversation about old age.

Meet the Headliners: Bianca Padilla & Jonathan Magolnick, co-founders of Carewell

Taj Kamranpour is co-founder and COO of portfolio company Stotles, whose Seed round we share today. Together with John Witt (CEO) and Carsten Schaltz (CPO) he’s building the operating system for business-government collaboration.

Current processes for businesses to work with governments are fragmented and time-consuming. Opportunities are missed, mistakes are made, and taxpayer funds are spent inefficiently. Stotles is helping reshape how $12 trillion in public procurement is spent by driving competition into the segment. 

Taj grew up in Ecuador, has worked in some of the world’s most extreme places, and is now building Stotles in London. He likes to chat and does so with humor and an ever-present sense of appreciation for his co-founders.

What’s something you learned early and still have fresh in your mind?

“Don’t half-ass it.” I was a high-energy kid. I’d get in trouble all the time. My teachers’ feedback was that I was capable, but that I’d rush things, finishing them quickly so that I could go out and play. My dad would always tell me to focus and to do the important things properly. By the time I finished high school, his advice eventually clicked. 

So much so that your first employer was a gold mining company. It doesn’t get any more practical…

Straight out of university, I joined Kinross Gold Corporation (One of the largest gold mining companies in the world) as an engineer. They sent me to Chile’s Atacama desert, then a small town in Nevada (USA), and then to Mauritania in West Africa. Tough places with people that work tough jobs. Learning how to build relationships in that context taught me to feel comfortable working with almost anyone, and I’m ever thankful for that time. Once you have to manage an infrastructure project out in the Mauritanian desert, across 3 languages, with people from 4 different countries, you’re pretty comfortable doing anything! I remember buying coca colas for the team from a trading spot out in the desert, the owner was always in the same spot and had a pet baboon that was an absolute menace… luckily we don’t have those kinds of challenges getting team meals in London! 

Give us a concrete “Doing Anything” example…

The mining company had water pipelines that ran for over 50 miles. One of them leaked, and a camel had been caught in the mud that was created from the leak . At 2 AM I caught wind and rallied our team, to go and get the sinking camel unstuck. On the spot, you think “this is not my job”. But then you immediately switch into gear to help this poor animal (which is often the entire livelihood of a local family). We got our hands dirty - and the camel out in one piece!

How did things continue, after you left Mauritania?

Eventually, I moved to the corporate headquarters in Toronto where I joined the Strategy team. Things got even more exciting there. I was able to work with brilliant people who taught me a lot about structured and efficient thinking. I got to focus on M&A, buying and selling gold mining projects around the world. It was a ton of fun and I got to work on some of the coolest deals of that time (like the largest land package purchase in North America at that time!) 

You are now building SaaS. Anything you miss, in the transition to software?

No. Even when you are working for a great, environmentally conscious company, it’s undeniable that the mining industry has a big ecological footprint. Stotles, if we get it right, is going to create a net positive impact. We can help every single person living in society today. Government procurement encompasses the roads we drive on, the hospitals we visit, the schools our children attend. Stotles is improving all of that, and that’s something that should get everyone excited.

Biggest contrast?

Product-market fit. The concept doesn’t exist in an industry that has been there forever and produces commodities (like gold). You don’t have to think about what the customer wants, you focus on operations.  In a tech startup, you have to obsess over it. 

In my mining days, I never felt the company was ever vulnerable. The outcome of my work couldn’t kill the company. Whereas in your early days as a founder, you truly feel the outcome of your actions. Emotionally, it’s very high stakes.

How do you keep sane?

I take at least one weekend day off. And two hours daily where I focus on something else, whether it’s going to the gym or going for dinner before returning to work. You have to keep your own mind clear before you ask everybody to bring their best self to work. At Stotles, everyone gets a monthly allowance of £130 to spend on well-being. It can be for a gym membership, for mental health services such as therapy, or anything else that helps you be the best version of yourself. 

But first, you had your startup internship…

As part of my MBA, I joined Fat Llama (a peer-to-peer rental marketplace). Strong founders, strong team. They taught me the basics of early-stage startups and opened my eyes to a new career. Most importantly, they showed me that you can test almost any assumption without having to spend a ton of money. No matter how much funding you raised. I took that over to Stotles. Eg. When we were MVP’ing Stotles in the early days, we used Tableau (an off-the-shelf interactive data visualization product), without even removing its logo and branding. And we still managed to sell contracts.

What do people get wrong about procurement?

I hate when people mention War Dogs (a 2016 movie that follows two-arm dealers who receive a U.S. Army contract to supply $300 million worth of ammunition to the Afghan National Army). There’s this strange misconception of public procurement being this super corrupt, dirty business. In reality, it is the backbone of our society and is a highly regulated industry in most places - making it complex to navigate as a business trying to sell to governments. It’s also huge (14% of a country’s GDP flows from gov to businesses). 

Any cringe moments while pitching this Seed round?

Most interactions were good. But one VC we pitched to insisted on how “data-driven” they are. We didn’t really have a conversation, we were told to answer specific questions so that the associate could fill out the form for their database. So every time we would try to tell the story we’d get cut off - it was a bit awkward, to say the least.

This was your second fundraising. What changed?

In the first round we were on our own. This time we had more experience, and the support of Jeroen (Art) and Toyosi (Ogedengbe) at Speedinvest. They were massively helpful in the lead-up, prep, and execution of the raise. I could spend ages on this, but if any founders want to chat on this I’m happy to dive deeper into the topic!

What’s something you are proud of?

Our team is pretty diverse, and that’s no accident. We focused on it early to make sure it compounds as we grow. From the moment we created job descriptions, we made sure they wouldn’t be tailored to one specific group or another. We interview in batches that are 50/50 male/female, both to hire a diverse group and to be fair towards everyone involved. There’s still much work to do of course: It requires constant attention.
 
You told me that if you had to, you’d write a book about the mesmerizing power of action sports. Why?
  
I have always loved the excitement of action sports, be that motocross or wakeboarding. You are doing something with your body that allows your mind to focus entirely on it to achieve something that’s normally reserved for the movies. The stakes are high, and the exhilaration you feel during and after is therapeutic. It gives you perspective and has a cleansing effect on the mind. I sound like a telemarketer now, anyway, I am sure someone more eloquent has already written a book about this!

Something you don’t like about startup culture?

There’s this “personality cult” element around startup founders. I don’t buy into it. It comes down to the collective group. In our case, the entire team is collectively responsible for any success (or failure) we experience. Yes, as founders we are leading the charge, but even then we are heavily reliant on the information and feedback we get from the team. Companies are built by teams, not individuals!


Meet the Headliner: Headline interviewed Taj Kamranpour, co-founder and COO of Stotles, an all-in-one platform streamlining public sector sales. Public procurement is fragmented and time-consuming. Opportunities are missed, mistakes are made, and taxpayer funds are spent inefficiently. Stotles is helping reshape how $12 trillion in public procurement is spent by driving competition into the segment.

Taj Kamranpour, co-founder of Stotles | Headline

Public procurement is fragmented and time-consuming. Opportunities are missed, mistakes are made, and taxpayer funds are spent inefficiently. Stotles is helping reshape how $12 trillion in public procurement is spent by driving competition into the segment.

Meet the Headliner: Taj Kamranpour, co-founder of Stotles. "I don’t buy into the personality cult. It comes down to the collective group."

Jordane Giuly is the co-founder of Defacto, an embedded B2B lending platform. Built with a “Capital by API” mindset, Paris-based Defacto allows companies to receive financing instantly, an antidote to the up to 4 months of processing time of traditional banking. A third-time founder, Jordane has previously built Spendesk, an all-in-one spend management solution that recently passed the billion-dollar valuation threshold and an unsuccessful first attempt that changed his mindset. After a Seed round led by Headline, Defacto announces today a $15M Series A round led by Northzone and an increased lending capacity of €400M annualized. Jordane speaks gently and jokes often, in the clear, optimistic, language of great product managers.


What is one early learning that shaped you?

To have fun. In a sense, my parents were my first business mentors. Both of them are entrepreneurs, and they started their company together over 26 years ago. Banking software for small banks: FinTech before the concept existed. They taught me about the importance of fun: When you work, you need to enjoy it. The moment you get bored is also the moment you become inefficient. With my co-founders Morgan (O’hana) and Marc-Henri (Gires), we have a routine where we ask each other: “Are we spending 80% of our time on things we enjoy?” If the answer is no, then it might be time to reshuffle our roles. Or to hire others who will enjoy those specific tasks.

How often do you run this exercise?

Once a quarter, monthly if necessary. As our company scales, our roles change often. So it’s extremely important that we enjoy ourselves in what we do, and communicate it transparently if we don’t. Making sure we enjoy our work is the only way to make sure we have the energy to carry out the tasks ahead.

When did you understand you were no longer enjoying your role at Spendesk?

In late 2019. Spendesk had passed the 150 employees mark. From three to one-hundred-and-fifty in three years. With the Series B round, it was all about scaling. It’s super exciting. But back then I realized I was more of a scrappy builder than an organizer. I thought my impact would decrease over time. It’s important to be transparent with your doubts. My co-founders understood me and we made sure all the operational tasks I was in charge of were covered by the time I left the company, just around the 200 employees mark. We left super amicably.


Yet, your former co-founder Rod (Ardant) is one of your first investors at Defacto. How did that go?

He was the first FinTech investor I sought. It was natural for me to think of him, and natural for him to invest. We believe in one another, whether it’s a co-founding or an investor relationship. Since leaving Spendesk, we never stopped being in touch. Both professionally and personally. I called him as usual, but with a concrete ask. It was a fast decision for both.

You have fundraised for three different companies by now. What have you learned?

That is a tough exercise. You have to create momentum, negotiate, and close the deal. It’s a lot of back and forth and you never know what is going to happen. And that selecting your initial cap table is more about finding smart money than finding money in the first place. We could have waited 3-6 months more before raising Defacto’s pre-seed. But we wanted long-term partners like Headline and GFC on board. The right investors can be a tremendous help. But after raising you need to know how to leverage them by being proactive with asks and intro requests. You want to stay top of mind with everyone.

What’s in your stack of self hacks to keep sane?

No meetings in the morning: They drain my energy. If I work on weekends, it’s reading and long-term thinking. Not for execution tasks.

And I try to stop working every day at 7.30 pm: I am not a machine. My goal is to arrive before my baby daughter goes to sleep. What’s the point of working if you don't get to see the people you love? Her bedtime is my hard stop. I organize myself around it: This is my routine. And it requires discipline. Eventually, you come to understand that as a founder, your work is never over. Every minute you don’t work is a minute you give away to your competition. It never ends, and it can only work if you give yourself both deadlines and boundaries.

Did you ever experience burnout?

Never. I attribute avoiding it to two elements: Having examples and reading about them. My parents are an example. They had a cool, successful company but would be home by 8 pm. A good reading to start from is the book “Rework” by the founder of Basecamp. It shows you that you don’t need to go crazy at work to call it a job well done. You are not a surgeon, nothing is truly urgent 99% of the time. You have to remind yourself that you have the right to have a work and life balance. 

What’s a pitch you still cringe about?

The ones of my first company, Rebble. My friend and I, both engineers, had just finished school. It was 2013: paper-only newspapers were in their last days, online-only publications in their early ones. We tried to develop a marketplace of contributions and contributors, a stock exchange for articles. We were so overconfident that we believed we didn’t need a business model. If Facebook and Twitter didn’t have one when they started, why should we? Let’s just say those pitches presented some big loopholes.

You must have felt pretty crushed afterward. How did you get over it?

Between Rebble and Spendesk, I was the first product manager at Coorpacademy, an EdTech company based in Paris. I learned a ton from the co-founders, who are serial entrepreneurs. It gave me maturity and humility. A failure can hurt your self-confidence. So you need to do something that rebuilds your set of assumptions about what being a good entrepreneur means. And being overconfident isn’t one of them.

What’s something that nobody tells you about being an entrepreneur?

At the very beginning, it’s almost a ping-pong with your customers. Your friends might find your ideas ridiculous.  You might have erratic days. Your people might have to work around you. You might feel lonely. Most importantly: you need to be selective with the feedback you receive. You start the company with a bunch of hypotheses, like “B2B financing is broken”. You interview all sorts of industry experts: If you listened to all of them, you would ultimately build nothing. Things are always complicated. There is always the argument that Google, Amazon, or somebody else can do it. You must keep everything in mind but make your pick. The real answer always comes from the market.

Continuing on this: What’s a misconception in product management?

That you are not done the moment your product goes live. You are done when people are buying your product. And product marketing is what connects the two points in time. 

You talk with customers, understand their problems, try to model them, come up with a solution, work with the engineers to deliver it, test it..and you think you are done. Wrong. Now you have to train your salespeople to sell that feature, make sure your users come across and understand it, and understand how to package it. 

At Spendesk, we started thinking about this role when the team was perhaps 20 people.  I think Spendesk started to really take off when we understood this and started having more product marketing resources.

Defacto reaches its series A with a purposely small team of fewer than 15 employees. What’s your experience with hiring?

Hiring is as much of a long-term play as it is an everyday routine. A good hiring pipeline means that you are sourcing and contacting candidates on a daily basis. Working in batches where you focus 100% on hiring only creates shocks and waves but never pays off. You need to be constantly asking for intros and meeting candidates for coffee. Maybe someone you think is great is not actively looking now, but they might be in one or two years. That’s the long-term part: You need to be yourself and kind, and keep in mind you might work with everyone eventually.

What’s a small change that made a big difference?

Understanding that you don’t have to focus only on the big things with zero-to-one potential. If you improve by 1% something you do 1000 times a day, then it’s a good return on investment. It’s good to be aware and work on the small things that take tiny bits of your time and energy every day. Using the Superhuman email client was too much for me, but I taught myself to use Gmail automation instead.

Big question last: How do you frame Defacto within the industry?

Finance will continue to be more real-time, cross-border, and context-based. Personally, I don’t believe mankind should pursue growth for growth’s sake, but rather for efficiency. Historically, finance has been about creating credit that value creation could redeem. In the 80s we started associating it more with capital markets and derivative products that eventually became much bigger than the initial underlying assets. We started losing sight. To me, finance’s purpose is to allow real businesses to stay afloat and grow. We created Defacto as an API-first infrastructure that allows credit to be delivered efficiently and instantly. To achieve the best possible cash efficiency and make sure every B2B transaction has a good impact on the real economy.

Meet the Headliner: "The moment you get bored is also the moment you become inefficient". Jordane Giuly is the co-founder of Defacto, an embedded B2B lending platform. Built with a “Capital by API” mindset. Headline led Defacto's Seed round, and doubled down in their Series A.

Jordane Giuly, co-founder of Defacto | Headline

"When you work, you need to enjoy it. The moment you get bored is also the moment you become inefficient". Jordane Giuly is the co-founder of Defacto, an embedded B2B lending platform. Built with a “Capital by API” mindset. Headline led Defacto's Seed round, and doubled down in their Series A.

Meet the Headliner: Jordane Giuly, co-founder of Defacto

When it comes to decisions in business or the kitchen, Shane Hegde honors the creative process. 

“Whether you’re cooking or starting a company, you have to wing it,” he explains. “I’m not following a recipe. You’re going to make a million mistakes, and they don’t matter.”  

Shane anchors that go-with-the-flow philosophy in his role as CEO and Co-Founder of Air, a centralized, digital workspace he built with former college roommate and best friend Tyler Strand. They developed Air. for marketing and creative teams to find, approve, and share content more easily –– recognizing that as companies across industries increasingly rely on compelling storytelling, teams need more organized systems to unlock creativity. 

We got in the kitchen with Shane as he cooked Butter Chicken Sandwiches and Kori Rotti, his favorite comfort foods from his home city of Mangalore, India. We discussed how he strikes a balance between driving organizational growth while enjoying the process – and the essential spices for flawless Indian cooking. 

You just pursued a trending method of fundraising via Operator Angels. Could you tell us about that process, and why you made that decision? 

We decided it would be great to pull together cash from folks who could teach us about our business and where it should go next. I think collectively across all of our fundraising we raised from 100 former CMOs, creative directors, and brand founders. Think: AllBirds, Harry’s, HubSpot, and SweetGreen, they’re all now investors in Air.

I think what’s really difficult is acknowledging the fact that I’m not the customer. I’ve never been a marketer. I've never had a marketing job. So, how do I build a product and a company that intimately understands what these people need? We could have tried to fake it, but the way we approached it was by bringing operators on as partners who provide real mentorship for myself and the team. 

How do you successfully leverage a skill set of 100 experts? 

I effectively got them to sign on for an hour every month. In that hour we can say, "Hey, you're a CMO of HubSpot, our Head of Marketing would love some perspective on how we're thinking about our performance marketing." Because, what am I, Shane, going to teach our head of marketing? It’s about being able to fill the gaps in my own knowledge.

You and Tyler were friends first – what’s your secret to co-founder harmony?

Tyler and I are spoiled as co-founders because we have a pre-existing relationship. We never put this company before our friendship. We legitimately just like hanging out with each other. We take the same approach in our 1:1s, I don’t know if it’s intentional or not, but we keep them unstructured by design. We have a natural rapport so we always end up just picking up where we left off.

How does your co-founder relationship influence Air’s company culture? 

For better or worse, our company is obsessed with this idea of really enjoying the journey. And I think that stems from our relationship. We laugh because we always say, "I don't know what else I'd rather be doing with my life and hanging out with one of my best friends." He's not here, so I can say all these nice things.

What’s something you’re trying to learn and why? 

I’ve been trying to get my team to work the way I do. And now I am trying to understand how others work and mold my management style. My most important meetings of the week are one-on-ones. Now, I do a one hour call with my reports, and we structure deep docs on what’s going well, what’s not, where we want to improve. They give me feedback, too. 

I do all six on Friday; it’s my favorite way to end the week. 

You’ve mentioned before that you believe every company will be a media company. What do you mean by that? 

Regardless of industry, I think it's really important to get out and tell the story about your business. The way that companies do that today is with content. You can do that with images and videos, newsletters and blogs. If we're going to keep living in this omni-channel world where there's a bunch of these channels that need content, then you have to be really thoughtful about the content that you create and how you distribute it. 

That's a media company. A media company specializes in storytelling through different channels. And at the end of the day, I think you can judge businesses by both what they're selling and how they're selling it. And yes, every business is not selling content, but how they're selling their services and their products is through content. And so, if that's going to happen, then people need the right infrastructure to be able to actually support that work.

Meanwhile, you’re elbow-deep in spices right now! Tell us what we’re having!

Anytime my mom comes back from India, she brings back packets of this spice from our hometown. You can’t make this dish (Kori Rotti) without it. It's a staple Mangalorean dish, which is where we’re from in South India. 

Can we convince you to share these recipes with us?

You lick it, throw some coconut milk in, and you figure it out along the way! Better than this recipe, here are the spices every Indian mom makes sure her kids have when they go out on their own: 

Meet the Headliner: When it comes to decisions in business or the kitchen, Shane Hegde honors the creative process. Headline got in the kitchen with Shane as he cooked Butter Chicken Sandwiches and Kori Rotti, his favorite comfort foods from his home city of Mangalore, India. We discussed how he strikes a balance between driving organizational growth while enjoying the process.

Shane Hegde, CEO and Co-Founder of Air | Headline

When it comes to decisions in business or the kitchen, Shane Hegde honors the creative process. Headline got in the kitchen with Shane as he cooked Butter Chicken Sandwiches and Kori Rotti, his favorite comfort foods from his home city of Mangalore, India. We discussed how he strikes a balance between driving organizational growth while enjoying the process.

Meet the Headliner: Shane Hegde, CEO and Co-Founder of Air

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…

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.

Meet the Headliners: 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.

Charity Majors & Christine Yen, Co-Founders of Honeycomb | Headline

Meet the Headliners: Charity Majors & Christine Yen, Co-Founders of Honeycomb

“There is always something that’s not going well literally every day,” he writes on his blog, which has the tagline: Musings about Startups, SaaS, Sales, Product Management, Philosophy, Productivity, and more. “Imagine if I keep worrying about such things every day. Life will be miserable and I will always be worried. That’s why I focus more on what’s going well and enjoy these achievements.” 

Since 2010, Aditya has published nuggets of wisdom and reflection like these on a regular basis. Other insights? Think of your actions as ‘experimentations’ that you’ll learn from instead of ‘decisions’ that are good or bad. Measure against your former self (retrospect) instead against others (comparison). And he has thoughts about everything from breaking your phone addiction to how to win competitive deals.

Aditya is applying his thoughtfulness and wisdom to Avoma, an AI meeting assistant startup that he founded in 2017 and now leads as CEO. We caught up with him to hear more about how his life philosophies—grounded in his spirituality—have guided him to where he is today.

We could all be better following the advice you talk about on your blog—worrying less, being more positive. How do you keep such a good attitude even if, as is often the case in the startup world, things get a little rocky?

I’ve always been very positive-minded since I was a kid. I think it comes back to the self confidence that whatever happens, I can rise back up. It's never too late. 

Was there a particular experience you had as a kid that instilled that self-confidence in you? How did you develop that philosophy so young?

I did not have a very great upbringing. Financially, my mom and dad struggled. There was no focus in my entire family about education. My mom and dad did not study, they had maybe a 10th grade education. But, there was one story I had heard growing up about two kids. They had alcoholic parents. One kid observed how his dad was an alcoholic and abusive and he said you know, that's how I'm going to live my life too. The other kid thought: I don't want to be like my dad, and I'm going to take a different path. This story stuck in my mind so clearly: you have to decide what your path is going to be. Your parents are not going to make the decision for you. Since that day onward, it was always a very crystal clear reminder: if I want to achieve something it’s completely on my own abilities. I'm not gonna say, “Oh, I was born in this little town with no resources.” If I put in my mind, energy and discipline, I can achieve it.

Was religion part of your upbringing as well? Did it play a role in how you think about the world?

I'm not a religious person, but I'm an extremely spiritual person. I think that's definitely the right way to put it: I do not believe in one particular religion. I believe in humanity, being positive, and assuming everyone is always trying to do good. Sure, there are bad actors. But still giving everyone the benefit of the doubt has always helped me.

Tell us more about your childhood. What was your family life like? How did you chart a path for yourself out of the small town in India?

We were a joint family in India. A joint family means that in one family, people don’t leave their parents—everyone just lives together and grows up together. Financially we were not a very well-to-do family. The key income source was agriculture, which used to result in challenging times, due unpredictable weather. There wasn't much importance given to education to find out other income sources. This constant financial struggle made me realize the importance of studies. So I would sneak out of the house to stay away from the negative thoughts and would rather spend my time reading books. Reading definitely helped me tremendously to keep learning the perspective that was beyond my little town, helped me start hearing perspectives of other people.

When did you start exploring entrepreneurship? Why do you think that was the right path for you?

I'm extremely bold. I don't worry about failure as much because as I've said, I know that even if I fail, I can come back. So just after 12th grade, it was a long summer vacation and nobody had any clue what we were going to do. The pool table was becoming a really popular phenomenon and we didn't have access to that in a smaller town. You had to travel to a bigger town or city to play those things and it was very expensive. So the idea at the time I had was: Why don't we buy the table and then charge people? It seemed crazy, but we bought the pool table, and got some money from each of our moms. We bought a shop. We had almost a club experience for people. Our friends started coming in and they used to pay us on an hourly basis, we used to run competitions to generate the buzz in the town. It was a very fun experience. We learned to manage money. We learned to pay people. My friends kept running it for many years after I went to a different city for engineering school. 

We named it "Yaraj Pool Club.” It was an acronym of my friends' initials – Yusuf, Ashish, Rohit, Aditya, and Jitin. "Yaar" means "friend" in the Hindi language. I guess I'm a fan of creating these acronym-based names—Avoma stands for "A Very Organized Meeting Assistant.”

What was it about the pool club experience that shaped your approach to being a founder today?

I think it was observing a problem, and jumping and trying to solve that problem and not holding back because no one had done it. Not thinking age is the barrier, not thinking experience is the barrier. At that time we didn't have something like that in the town, and we were doing something unique. We took inspiration from what was happening elsewhere in the world and we brought it to our people. And that applies to everywhere: if you observe a problem, do not hold it back. Have a point of view, have a creative mindset and try to solve those problems.

You mentioned the pool table business was one of your first bold decisions—what’s another example of a bold decision and where did it lead you?

I came to the U.S. as an immigrant on an H1B visa and I was employed at a large public company. I wanted to start my startup, but without a green card you can’t, and the green card was taking a long time. I was getting frustrated. I told my manager, “I want to take a break. You don't have to pay me any salary. Just keep my visa legal here.” So I didn't have any health benefits or salary for 6 months and worked on my first startup.

Out of nowhere, right around the time when my 6 months was ending, I got my green card. I told my manager I need to leave the company, officially, because I can start what I've been working on. He told me at the time: stay employed here. Come to the office two days and work on your startup the other 3 days. You're just answering to me, but you will get full salary, full benefits. It was an extremely lucrative option and my first kid was about to be born.

Everyone thought I would be crazy not to take it. But I realized at that time that it would be a mistake. I thought if I'm going to fail, I would rather fail by giving 100 percent, and I don't want this distraction at all whatsoever. So I declined that offer. 

That’s a lot of pressure with a newborn on the way! How did you manage it?

No pressure, no diamond. That's one of the things I always live by. I know that if I'm being pushed, if I’m being tested, if I feel like so many things are going against me. That means the pressure is being applied and it's going to happen. It's going to work out, and it's just a matter of faith and having perspective that always helps me address any kind of adversity, any kind of negative thing that happens.

But then what do you do with the pressure? How do you turn the pressure into something good?

One of the things that helps me to manage stress in general is to not feel like the Atlas Shrugged, where I carry everything on my shoulders. I think the best way is to break it down. Take the small first step. Even that little first step gives a little bit of momentum. That you feel that there is not a block anymore, that takes you to the next little step, and that's how eventually you don't feel the stress as much, and then you're able to still enter the progress. 

Meet the Headliner: Aditya Kothadiya is applying his thoughtfulness and wisdom to Avoma, an AI meeting assistant startup he founded in 2017 and now leads as CEO. Headline caught up with him to hear more about how his life philosophies—grounded in his spirituality—have guided him to where he is today.

Aditya Kothadiya, CEO & Founder of Avoma | Headline

Aditya Kothadiya is applying his thoughtfulness and wisdom to Avoma, an AI meeting assistant startup he founded in 2017 and now leads as CEO. Headline caught up with him to hear more about how his life philosophies—grounded in his spirituality—have guided him to where he is today.

Meet the Headliner: Aditya Kothadiya, CEO & Founder of Avoma

Steve Wen views his life as a countdown. It’s a feeling that has guided his decision-making since childhood.

Like when he was six and visited the U.S. for the first time, he decided he wanted to live there. His parents agreed, and soon they moved from China to Los Angeles. Their dentist licenses didn’t transfer to the US. Steve’s parents started their own port logistics company to make a living.

Then, there was the time he decided to drop out of U.C. Irvine to become an entrepreneur. His parents didn’t agree with this choice, wanting him to graduate and seek a stable profession. Little did they know, he would ultimately follow in their footsteps and launch Dray Alliance: a port logistics company that uses data and analytics to modernize drayage-—the process of transporting massive shipping containers from ports and rail yards to local warehouses. Steve’s knowledge of the business dates back to working in his parents’ warehouse as a kid.

As his life-long countdown continues, Steve is looking to build Dray Alliance into a global business. We caught up with Steve at the shipping port in Long Beach, CA. It’s one of the two largest in the U.S., meaning virtually every home in the country has something that came through the Long Beach port. As we walk between shipping containers from all over the world filled with everything from food to household goods to toys—“Your Christmas present could be in here!” he says—Steve delves deeper into those life-changing decisions that lead him to Dray Alliance, and what he sees on the horizon.

Take us back to your first visit to the United States. What was it that made your six-year-old self want to come back so much?

It was actually very simple: I liked basketball.

Well, that was one thing. It was also that America was this land of the free where there was so much opportunity for my personality. I didn't grow up to be the most obedient child in China, where the culture was very much: be a good kid, earn good grades, take the equivalent of SAT and go to a good college. Everyone was on the same path. Having that freedom of experimenting, of doing what I wanted to do was very important to me. America seemed like the right place.

What’s something about your childhood that still influences you to this day?

Since I was 10, I started thinking about my life as a countdown. There are too many things that I am curious about and too many people that I care about, so there's an opportunity cost to every decision that I make. After this realization, I started to form a number of frameworks for decision making that I still use today from making highly impactful business decisions to mundane tasks in my personal life.

Is that what led you to drop out of UC Irvine and start down your path as an entrepreneur? How did you end up turning back to the world of shipping and logistics?

At UC Irvine I learned a bit about computer science and finance, and I started small businesses. Some of my original ideas failed and I eventually went into the ecommerce space due to the high likelihood of successes. I sold my ecommerce company, but that experience got me in touch with the supply chain. I saw that there had been virtually no change in how my parents’ business operated. The last mile of container freight was a common source of frustration across the industry. I noticed nobody seemed to like each other. So something had to be wrong. Before Dray Alliance, it was all fax and paperwork. Guys had to spend their Saturdays comparing paper checks to their invoices to make sure they had been accurately paid. So of course, they were extremely unhappy! So that’s where I focused my attention. 

But rather than start Dray Alliance upon seeing this business opportunity, you actually started a different company first. Can you tell us a little bit about that decision?

We knew there was a problem, but I didn't want to be a founder who doesn't truly understand the industry pain point. I believe what drives me is seeing how things are done in action. And being truly part of the stakeholders in these transactions would allow me to see the reasons behind everyone's frustration. There's no better way of doing that then being a future customer of myself. So before I started Dray Alliance, I started a traditional drayage trucking business.

I wanted to be as deep as possible. I wanted to be living in it. I wanted to feel the frustration and inefficiencies in my bones. It was a very difficult decision, because I knew it would lead to a lot of pain and, likely, I would not earn a profit. But I wanted to feel it before I started on something bigger. The other reason was also that this time around, I wanted to build a massive business. I didn't want to have any questions that I couldn't answer. We tested as many ideas as possible during that time and got really familiar with the nitty-gritty. After about a year and a half we felt we’d learned enough and started Dray Alliance in 2018—you can think about it like DoorDash but for massive shipping containers. 

Did your parents support you in that process? Did they help you with insight into some of these pain points?

I think they didn't agree with my choice of dropping out of college. They didn't fully agree with my decision of starting my own business at a younger age. They wanted me to find a more stable job. So there was not a lot of support from them. It was helpful, but they definitely raised a lot of questions and tried to persuade me to not do it.

When we first started the trucking company, my parents’ warehouse was our first customer. And we actually launched the business in the backroom of their warehouse with no windows and no AC. It's in the Inland Empire as well, so it got up to 120 degrees sometimes.

That’s a lot of pressure to have your parents as a customer! Do they use Dray Alliance in their business today? How do they feel about your decisions now that Dray Alliance is growing?

They have since retired—and I'm happy that they have retired. Although they did not agree with me, my mother put in almost all of her savings into the company as a first investor. So she's happy that the company is increasing in value.

My greatest regret is not being able to listen to my grandfather tell his story. He grew up in a war between Japan and China, then was able to participate as a decision maker in the post-war international relationships. There are many stories that have forever disappeared when he passed away. I wish I was able to record his stories and share them with more people.

By the way, what became of your basketball dreams?

I didn't go to my first game until I had enough money to pay for a ticket myself. It felt great, but I was also saddened because Kobe [Bryant] had retired already. It was in college, a Clippers game.

There's so much to build because there are so many problems to solve. All of the shipping news we're seeing today, where ports are backed up, every port in the world now has a backlog of container ships waiting to unload. And that's insane. What that means is that the consequence of all of these delays will affect years to come in supply chains. And we're in a changing world order in a way, where the current system was built in the eighties and nineties. So I think there's a real opportunity for us to build the 21st century infrastructure for global shipping, starting from the last mile. 

Steve’s entrepreneurial drive and his deep understanding of the logistics business made an immediate impression on our team here at Headline. Dray Alliance is uniquely situated to meet a large addressable market; and by digitizing the container trucking industry, Dray Alliance drives efficiency and accountability in this last mile of the supply chain. Our Fund VI will lead the company’s Series B financing round.

Meet the Headliner: Steve Wen is the CEO & Founder of Dray Alliance. He views his life as a countdown. It’s a feeling that has guided his decision-making since childhood.

Steve Wen, CEO & Founder of Dray Alliance | Headline

Steve Wen is the CEO & Founder of Dray Alliance. He views his life as a countdown. It’s a feeling that has guided his decision-making since childhood.

Meet the Headliner: Steve Wen, CEO & Founder of Dray Alliance

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!

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. 

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?

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.

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.  

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. 

Meet the Headliners: Nicole Clark & Alon Shwartz co-founded Trellis, an AI-powered research and analytics platform to make state court trial data accessible for the first time. Headline 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.

Nicole Clark & Alon Shwartz, Co-Founders of Trellis | Headline

Nicole Clark & Alon Shwartz co-founded Trellis, an AI-powered research and analytics platform to make state court trial data accessible for the first time. Headline 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.

Meet the Headliners: Nicole Clark & Alon Shwartz, Co-Founders of Trellis

Few companies can claim they are creating an industry: Homa Games is one of them.

It’s a complete tool stack that allows indie game creators to speed up development and compete with much larger studios. They provide intelligence, distribution, and monetization while game developers can focus on their creativity. 500 million game downloads and a $50M Series A round in, I sat down with co-founder and CEO Daniel Nathan to chat about company culture, painting as an antidote to emailing, and getting lost in the forest.

Let’s jump straight into it. Where does your itch to build come from?

My parents weren’t business people. But they would tell me stories about my grandfathers. One ran hardware stores. The other had a candy shop and a horse betting business on the side. I  met them maybe  10 times in total in my life: They were in Morocco and the UK, we were in France. In my mind, I made up movies about what great entrepreneurs they were. My mom would tell me that I was like them, that I could achieve all I wanted. I was growing up as the internet was growing up: As soon as I discovered blogs, I would read any entrepreneurship post I could find. Loïc Le Meur, TechCrunch when Michael Harrington was the sole contributor. I got the entrepreneurial mindset from the stories of my grandfathers and the internet gave me tech role models.

How smoothly did things turn out? Why Paris via Berlin?

In France, the name of the school you attend matters. When I was young, people would call me ambitious, and I was like: Yeah, I am. I really wanted to get into the best school. I didn’t and felt extremely frustrated, I struggled a lot because of it. I told myself that I might not be the most qualified academically, but that I’d be the best in business. That was a defining moment for me. I left for Berlin, Germany to go where nobody knew me and start from scratch. Years later, I realized how hard it was to hire talent there. Paris was not hyped and had plenty of engineers, so I decided it’s where I’d build Homa Games.

In a way, Homa also comes from a certain frustration you felt…

My previous companies were in AdTech, with a focus on user acquisition for games. It’s a tough value proposition. You get compared all the time to the performance of Google and Facebook, two walled gardens that have access to all the data and all the content. Their pitch is easy and you cannot fight it. I knew they’d never let us work in a level playing field against them. It frustrated me immensely: We had to have “our” content. We knew about user acquisition and monetization, but nothing about building apps. So we thought we could partner with those who did. We were used to companies that would spend 12-18 months prototyping a game before putting it in front of their users. These indie developers would have users test their games after two days. We realized how “easy” it is to build games compared to the challenge of finding the right ideas and distributing them. We saw we could offer a support layer on top of game engines and do something entirely new.

What were you completely wrong about?

In hindsight, it’s crazy. But we originally thought we needed to offer game design support. We were absolutely wrong. We needed more data analysts, to look at the data and clearly show game creators what their users are doing, signal why they churn, and better support with distribution and monetization. Today Homa is all about providing better and better data, not about influencing design choices.

Meet the Headliner: 500 million game downloads and a $50M Series A round in, Headline sit down with co-founder and CEO Daniel Nathan to chat about company culture, painting as an antidote to emailing, and getting lost in the forest.

Daniel Nathan, co-founder of Homa | Headline

500 million game downloads and a $50M Series A round in, Headline sit down with co-founder and CEO Daniel Nathan to chat about company culture, painting as an antidote to emailing, and getting lost in the forest.

From the Team