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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

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

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

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

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

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

Stefan Ytterborn founded CAKE, category-defining electric motorcycles that push the world closer to zero-emission mobility.

Based in Stockholm, Sweden, he built 7 companies including popular sport helmet and apparel manufacturer POC. In his long career, he also introduced the IKEA PS product category in an effort to re-launch Swedish design in the 90s!


We met in 2019, referred by our good friends at Creandum. Stefan's relentless drive and energy to build an electric urban mobility brand stopped in our tracks. We had to join.

What words would your enemy use to describe you?

Too optimistic. Too naive. Too much of a risk-taker.

The largest risk you took?
Starting POC. My background was in design and architecture. POC would make protective sport gear. People told me how brave I was by moving in a completely different direction. It didn’t feel so for me. I was still developing products to support a certain meaning. I didn’t feel I was taking a risk. It’s my own personality. When I need to do something, that thing becomes a matter of survival. I have ambition for purpose, innovation, performance, and quality. If I don’t implement my convictions, it kills me. Implementing keeps me going.

Something your parents told you that still influences you today
To try again and not give up. My mother was a gym teacher. She introduced my brother and me to all sorts of sports. Competition is the fun side. It’s not only about winning. It’s about perseverance and patience. Learning until you achieve something. Potentially my main driver, to this day.

The moment you thought your career would fall apart...
In 2008, athlete Scott Macartney was wearing one of our helmets in the Kitzbühel downhill competition. He failed the last jump, at 145 km/h. The fall was terrifying. He hit his head and his POC helmet split in two. Unconscious. My phone started ringing: Newspapers from all over the world wanted to know why the helmet we made could break. It was our second year in the World Cup circuit. Our brand was new and cocky: Lots of people wanted to see it fail. I called Scott’s parents and promised a full investigation. We realized the helmet had been designed to break on high impact, to reduce the amount of energy passed. Scott had experienced forces 26x higher than what tested for. The helmet saved him. His fast, full recovery became our proof of concept. What could have ended our company accelerated us.

What’s something people often misunderstand about you?
Despite working around design my whole career, I am not a designer myself.


Directing design processes is what I do. My key competence is in maintaining an understanding of things. It’s never a one-man show. I liken my role to that of the orchestra conductor. It’s not about mastering the violin or the trumpets. Rather, to make sure the intended kind of ambition is materialized to serve your market. I was lucky to work with some of the top designers in the world: It’s very old-fashioned to look at the artist as full control of delivery. Today’s society is way more complex than Renaissance’s. To succeed, there are many competencies that must interact and optimize each other.

How does it influence your approach to product?
For me, sustainability passes through physical and aesthetic qualities. Achieving both engineering and design leads to extended product lifecycles. Two items that can become classics and be passed down generations. I want to build bikes that will be sold in auction houses one day. The biggest challenge our planet faces is our own pace of consumption. I don’t believe customers really prefer low-quality items to throw away and buy anew.


But lack of financing options leads to faster and faster consumption.

What’s something nobody tells you about being an entrepreneur?
There’s this idea of overnight success. That running your own company is a run in the park. Reality: Most founders put more time and effort into what they do than the average person does. It’s a job where you solve problems that never stop appearing. If you are not willing to accept it as your reality, you must get out. Enjoying it is what entrepreneurship is about.

Something you disagree with...
The exit mindset. Young business school students are taught to develop business concepts with a clear exit perspective in mind. It’s not just about getting rich. To make a dent in the universe, you must be meaningful. There are other drivers but money to prioritize. I consider this a consequence of today’s speed of capitalism, and it disturbs me.

When did you know you had to start CAKE?
The first time I saw an electric motorcycle. It spoke to me. I could see myself on a trail in the woods without disturbing the forest or polluting it. I tried electric motorcycles from different brands, with no intention of starting a business. I saw how electric would flip the motorcycle industry upside down, if only for its simplicity. It’s akin to padel and tennis. Tennis is beautiful but complex. Everyone can play padel. With electric motorcycles, there is no clutch. No gears to change. Limited maintenance. And it meets our obligations towards planet Earth.

What were you wrong about?
At the start, I didn’t have enough competence around drive trains. I was eager to launch with something super simplistic. I thought we could buy medium-quality hub motors (rear wheel) off the shelf, from China. That’s what most of the industry was doing. When I started riding and training with professional off-road riders, I realized a hub motor would have killed the experience. We could do so much better. I shared with my investors these conclusions: We had to rethink the bike for a belt-drive motor. We stopped everything and postponed the launch for one year. Mistakes big and small happen all the time. As long as you realize you are more successful by making mistakes, you’ll have a forward motion. That’s my general philosophy.

Meet the Headliner: Stefan Ytterborn, founder of Cake. Based in Stockholm, Sweden, he built 7 companies including popular sport helmet and apparel manufacturer POC. In his long career, he also introduced the IKEA PS product category in an effort to re-launch Swedish design in the 90s! Stefan's relentless drive and energy to build an electric urban mobility brand stopped in our tracks. We had to join.

Stefan Ytterborn, founder of Cake

Stefan Ytterborn is the founder of Cake. Based in Stockholm, Sweden, he built 7 companies including popular sport helmet and apparel manufacturer POC. In his long career, he also introduced the IKEA PS product category in an effort to re-launch Swedish design in the 90s! Stefan's relentless drive and energy to build an electric urban mobility brand stopped in our tracks. We had to join.

Meet the Headliner: Stefan Ytterborn, founder of Cake

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“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. 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.

Aditya Kothadiya, CEO & Founder of Avoma

Aditya Kothadiya is applying his thoughtfulness and wisdom to Avoma, an AI meeting assistant startup 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.

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

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

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

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.

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.

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.

Meet the Headliner: We covered Julie Wainwright’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.

Julie Wainwright, founder of The RealReal

We covered Julie Wainwright’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.

Meet the Headliner: Julie Wainwright, founder of The RealReal

From med school hopeful to founder of a telecom company, from Airbnb host (for his own bedroom) to launching Cape Cod’s largest hotel chain, there’s no predicting what Yury Yakubchyk will do next. 

The last 18 months are no exception. In that time, Yury transitioned from the hotel industry to founding Elemy, which provides in-home applied behavioral analysis (ABA) therapy to children with autism. He raised two rounds of funding. He grew the company’s headcount to over a thousand. Today, Elemy is one the fastest-growing companies of its kind in the United States. 

I caught up with Yury to learn more about this circuitous path, the opportunity for changing autism care, and – how he does it all while keeping (an almost completely) empty calendar.

Elemy is not your first company – take me back to the beginning. When did you first get the itch to start something?

I started a telecommunications business in my early twenties, right after graduating college. I went on a trip abroad with my friends from high school, and we all had these crazy cellular data roaming bills. We were like, "We’ve got to create a better experience than that." So, we started a consumer wireless company called Wing. 

The telecommunications business had a very slow start. So while I was launching Wing, I had some Airbnbs to make ends meet in New York City.

...you were working the Manhattan Airbnb scene to make ends meet?

I had a three bedroom and I started living on the couch and renting out my room. I was like, "Wow, this is $180 a night." I was sleeping on my own couch. I was eating from fruit stands in Manhattan for half my meals. I was doing some tutoring. I taught myself how to code to do some freelance stuff...but the Airbnb thing was pretty gritty.

How did your roommates feel about waking up to you on the couch and a stranger in the bathroom?

Honestly, I think for the first five months, they thought it was hilarious. They were very supportive, thankfully. One of the other guys was an entrepreneur. At a certain point, he started renting his room out too. The third roommate eventually moved out. So that's how we got our first empty apartment. Eventually I had maybe 15 or 20 apartments. 

I got to meet a lot of international travelers from all over the world. I loved listening to their stories, hearing about their unique backgrounds. So I called a friend from college named Rami Zeidan. We started Life House on this idea of getting people together, big open communal spaces—no front desks, none of this tacky, weird, old hotel stuff. And the business ended up growing to the point where now Life House manages dozens of hotels all around the country. Today we're the largest hotel management company in Cape Cod and Nantucket.

Meet the Headliner: Yury Yakubchyk is the founder of Elemy. Yury's unbridled energy – and mission to improve the lives of children with autism – instantly won over our team. We invested in Elemy's Series A, and doubled down with a follow-on from our Growth Fund in Elemy's Series B.

Yury Yakubchyk, founder of Elemy

Yury Yakubchyk is the founder of Elemy. Yury's unbridled energy – and mission to improve the lives of children with autism – instantly won over our team. We invested in Elemy's Series A, and doubled down with a follow-on from our Growth Fund in Elemy's Series B.

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