Greg Stewart of Ladder: 5 Things I Wish Someone Told Me Before I Became A CEO
By: Alexandra Spirer
Tags: CEO, Entrepreneur, Teamwork, Team

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I spent the first half of my career in finance, most of that time in investment banking at Goldman Sachs covering technology companies. When I got the opportunity to move to San Francisco with Goldman, I developed a much deeper appreciation for startups and entrepreneurs. In New York, my peers leaving Goldman were going to work in private equity or at hedge funds. Meanwhile in San Fran, the finance professionals I worked with were joining venture capital firms or taking operations roles at startups. It was a completely different world. The people I knew at startups were scaling their responsibilities incredibly quickly, they were solving interesting problems, and they were also just really excited to go to work every day. I quickly found myself gravitating toward those same startup rocketships and the endless possibilities that come with that world.

I loved and appreciated my experience at Goldman — it absolutely changed the trajectory of my career. But I eventually felt like in my role at Goldman I was outside the glass looking in. We were interacting with entrepreneurs, helping them value their business, and preparing later staged startups for IPO… but I didn’t feel like I was building anything myself. So, eventually I decided to leave investment banking to join a startup in Mountain View that was building a mobile ad network and creative platform. I joined as Head of Business and Corporate Development, which meant distribution partnerships and helping raise capital. It was my first glimpse into how a company worked. I sat on the executive team, I interacted with engineers, product people, sales leaders, ops people…you start getting a sense for all the pieces of the machine, how they work together and how they are dependent on each other. I loved it. I loved the rush of solving problems together, across each of these facets of the business.

After this role I joined a start-up in Austin, TX that was focused on building software tools for the residential and commercial real estate industries. I was hired to help the founder manage the business and the leadership team, and prepare the business for its next phase of growth. I ended up becoming CEO of that company after the business experienced a rough patch, and helped manage the business through a product pivot and rebuild of the company culture. This experience served as a crash course in all things leadership and change management.

A few years later, I was hired by one of our investors to join Amherst Residential. With DNA in real estate, financial services and technology and data, Amherst had been very successful in partnering with institutional investors to acquire, rehab, and maintain single family real estate across the country. At Amherst, I helped build an innovative consumer business that we would name Bungalo, which would sell a high-quality renovated home directly to a consumer home buyer. Our products were both the home itself (freshly renovated, well designed, built for today’s consumer), and also the experience of purchasing and financing the home. I got to build a leadership team and then a broader team around them from scratch, bringing in people from consumer, tech, and entrepreneurial backgrounds into Amherst. We built an incredibly talented product and engineering team and built a technology platform that digitized every inch of the home buying experience.

Eventually I got the itch to go back to early stage company building again and left Amherst to join Ladder. I was introduced to Ladder by Tom Digan, Ladder’s President & Co-founder. We went to college together and kept in touch. We both started in finance and ended up building consumer businesses in Austin, TX. I had tremendous respect for Tom. I wanted to stay focused on consumer and building transformative products and brands, and I wanted the opportunity to build a team again, and bring together the exceptionally talented people I’ve been lucky to work with over the years. Ladder was in a very early stage, but I could see the potential of what the business could become when I joined in Nov 2019.

Can you tell us a story about the hard times you faced when you first started your journey?

I joined Ladder in November 2019, and spent the first few months helping manage the business through a leadership change and essentially a rewrite of our culture and the core values that guide how we serve our customers and each other as a team. In early Q1, after I had a much better handle on the business, it became clear that the core business, which was an app that connected trainers with people looking for a personal trainer, was not going to be a business that we could anchor our future to. The fundamentals of the business were not in a great place, and we had learned that a consumer fitness subscription product only works if you are able to maintain the quality of the coaching, which was difficult working with independent coach partners across the country. We also learned that a key missing piece to the product was community, and that creating shared experiences, and social accountability and motivation is incredibly powerful in this space. We had been testing team-oriented training products and saw really strong signals so we decided to go all-in on a major pivot…moving away from the business the company was founded on and focusing on a smaller group of elite coaches and a team-oriented training experience where one trainer can work with a larger number of people, and where accountability and motivation is garnered both from the coach and the team. And we married this team experience with a best-in-class press-and-play workout experience.

As part of Ladder’s new journey, I recruited a new leadership team, essentially the best people I’ve ever worked with, with a mandate of building this new product and business from the ground up.

Then COVID hit. We were fortunate that this new business could thrive in a COVID world where people are working out at home. But this meant we had to switch to a fully remote team when most people had just recently joined the team, and in a time when collaboration and connectivity was mission critical in planning and building our new business. It also made fundraising very challenging.

Thankfully we made it through and this experience has made us stronger and has bonded us together. We designed the strategy, built the technology, and recruited our initial coaches in exactly 100 days, starting in Mid March, right when COVID spread was accelerating across the nation.

Where did you get the drive to continue even though things were so hard?

For better or worse this is the second business transition I’ve led, both for early stage startups, but the first experience helped give me perspective and a framework for managing a team and a business through difficult change. The driver for me is the team, and knowing that when we come out on the other side, the experiences we shared, while difficult, will define us and bond us together, which only makes us stronger as a team and business going forward. I want to be working with these people, and it was worth fighting to keep the business moving forward and this team working together while building incredible products that have the ability to change the world.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Not really a mistake, but one fun fact about me: I commuted to Austin from San Francisco every week for 4 years and for 2 jobs in a row. For the first role in Austin we were an early stage startup with very little money so my travel was economic to say the least. I took connecting flights both ways because they were cheaper, and when I wasn’t staying at team members houses (which was frequent), I was staying in some of the cheapest, dirtiest hotels and motels you could imagine. When I landed in Austin I had no idea where I was staying that week. Either a teammate would let me crash or I’d find something for $20 a night or less on a last minute discount site. While I wounln’t want to do this again, it was all part of the journey.

If you could go back in time and talk to your younger self regarding life lessons, things you would like him to know, what would they be and why?

I think the biggest influence was my time spent leading a challenged start-up that needed a lot of work to get back on track. Money was tight, morale had hit a rough patch, and I realized that all we had was each other. It wasn’t about titles or resumes or college logos. It was about coming together in the trenches to win as a team. Everyone has something to offer, regardless of what role they are in or how you perceive their resume. What motivated the team was the team itself! Working together and seeing results. It’s easy to do weekly happy hours and team events, but it’s harder to win as a team when the mountain to success looks impossible to climb.

My two biggest learnings from this experience were 1) team and culture matter most. If you don’t nail both then then the odds of success are slim, and 2) transparency is an incredible motivator. When everyone understands the objective and how they are contributing to the mission, and then sees and understands the results, it’s magical what can be accomplished.

I also learned a ton in my first job out of college. I began my career in investment banking in New York City, just as the market was reaching its peak. Two years later and after many sleepless nights at work, I was unemployed and interviewing for entry-level financial services roles in the hardest job market in recent history and in the most competitive city in the world. I saw many of my friends pack up and head home, leaving New York and the industry before their careers had really started. I spent nearly a year unemployed, while trying my best to maintain a positive attitude, and I treated interviewing like a full time job. I was fortunate and finally found a great role, but learned to never take anything for granted, that nothing is guaranteed, to expect the unexpected, and that you have to fight hard for anything that really matters.

What do you think makes your company stand out? Can you share a story?

The people. Hands down.

In mid March, our small, but scrappy Ladder Team set out to completely shift our business and build from scratch what would become our flagship product while working remotely. As I mentioned previously, this feat was accomplished in 100 days, and the success of our launch is due entirely to the hustle, passion, and collaboration of every single person on this team. At Ladder, it’s always “where can I jump in?” not “that’s not my job.” When you find yourself surrounded by a group of talented people who are bound and energized by a sense of community and a common mission, you know you’re onto something special.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Our team does work hard, but we also have a ton of fun together, both in and outside the office. Before COVID, it wasn’t uncommon to find our team working hard shoulder-to-shoulder all week and then hanging out together on the weekend. We enjoy each other’s company. It’s a high energy and very collaborative group that knows when to focus and when to kickback. Keeping this balance as we grow is critical.

Managing a fully remote team during a global health pandemic brings a unique set of challenges. The line between work and personal time gets blurred. Creating authentic moments for the team to bond is difficult. We do virtual team lunches, weekly all hands on Friday afternoons, and other virtual team bonding events that keep it fun and bring folks together for casual conversation. We also added non-work slack channels, like #quarantine-eats and #netflix-trending to promote ‘water cooler’ conversation.

In terms of burn out we definitely encourage the team to take time when they need it and to block your calendar for ‘me time,’ whether that’s family lunch or dinner, workout time, morning coffee with your spouse….these moments should be sacred and they are important to avoiding burnout and keeping everyone functioning at their best.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

One of the best pieces of career advice was shared by my father, who stressed the importance of building meaningful work relationships. It all comes down to people and the opportunity to forge real relationships with a diverse group of people who share common goals but offer new perspectives on work and the world in general. When you build relationships at work that are grounded in trust, collaboration, and respect, you are building relationships that will last long after your work together comes to an end. Some of my closest friends and mentors are prior colleagues. These relationships have opened doors in my career that I never would have imagined. I invest heavily in maintaining and growing these relationships (friendships really) and making sure that I am adding value to their lives and careers as well.

I encourage everyone on my team to recruit their own personal board of directors. Folks they can lean on when they are stuck, or brainstorm new ideas with. The majority of my personal board of directors are former colleagues from throughout my career.

How have you used your success to bring goodness to the world?

The beauty of focusing on consumer is you get to build products that impact people’s lives every day.

At Bungalo we were helping people buy a home, and for many it was their first. Every day our team was thinking about how we can make it easier and more enjoyable to buy, sell, finance or invest in a single family home, the biggest purchase of people’s lives.

At Ladder we are focused on fitness, and making it easy and fun to train with the best coaches in the world while supporting and being supported by others around you. We are building products that literally make our members healthy, happy, and more confident, and we are creating meaningful shared experiences and connectivity.

At a micro level it’s been amazing to work with a group of the same people for many years. We are learning a ton together everyday, and when you step back and reflect a bit it’s really incredible to see how far we’ve come and how much we’ve all developed through these experiences together.

What are your “5 things I wish someone told me before I started my company” and why?

It’s all about the people…the who before the what.

It’s going to be 100x harder and 100x more rewarding than you think.

You can’t hire on resume alone…Pick hustle, creativity, curiosity over pedigree. AND…never hire the asshole. NEVER.

Any one thing might feel world/business ending, but it very rarely is…keep going.

Focus and prioritization is key…you can’t do it all…you have to pick what matters most and point the entire team at that.

Build a culture where you can have the hard conversations without it impacting relationships, both up and down your organization

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I truly believe that the experiences we’re building at Ladder right now have the potential to create a movement and change lives. At a moment in time when people are missing their studio workout classes, their gym families, and human connection in general, our team has created a fitness experience that brings entire communities of people together to lift each other up toward healthier lives.

How can our readers follow you on social media?

Ladder

Instagram: @joinladder

Facebook

LinkedIn

Greg Stewart

Twitter: @gregoryfstewart

LinkedIn