I had the privilege to sit down with Tailwind’s co-founders, Danny Maloney and Alex Topiler, to talk about our company’s culture. The exact reason I told myself if I could work anywhere, it would be here.
Why did I want to work for Tailwind so badly?
As a newly single mom who had just moved to Oklahoma City, when I researched the “best family-friendly tech startups to work for,” I noticed Tailwind listed on every website.
I took a closer look into Tailwind and found Glassdoor reviews talking about the flexible life balance for parents and the humility of the founders. Add yearly team trips, free snacks in the office, ping pong tournaments, and six key values that define the company (listed below).
I quickly realized Tailwind was not only passionate about the quality of their product but motivated by the happiness and growth opportunities for their team members too.
Here’s a snippet to show how committed Tailwind leaders are to their teammates’ growth and to give a glimpse into the type of culture Tailwind has ➡️
Tailwind is a company unlike anywhere else because of its founders, Alex and Danny. And their extraordinary idea of putting the structure of Tailwind’s culture into the hands of their team members. (We’ll get more into that later. )
Every company has a culture, and while many brag about it, few are authentic. Now, let’s dive into some radical candor about how Tailwind established and maintains a culture that feels like a family.
Alex and Danny met at Lean Startup Machine, a weekend hackathon in New York “geared towards people who wanted to be founders but needed to learn how.”
Both co-founders had jobs in big corporations and longed for more which led them to this event.
Alex had been working at a large financial institution, and Danny at some of the most prominent and influential companies: Google, YouTube, and AOL.
They didn’t realize it at the time, but this hackathon would be a catalyst for their dreams materializing.
“When we went through that experience (weekend hackathon), we got really good feedback on the concepts we were building. That’s when we said, “Hey, you know what? There might be something here. We should keep doing this. We shouldn’t just let it end this weekend.”
It was through meeting up on nights and weekends while still doing our full-time jobs that we began to realize we work really well together in a bunch of different ways. It’s a little bit like dating before marriage. But it happened organically in that way.”
Alex Topiler, Co-Founder of Tailwind
This won’t be the first time “family” is brought up. Throughout this interview both Alex and Danny mention the “marriage” of new team members into the company and a desire to create a mutually supportive environment.
While Alex and Danny found a flow in their working relationship, Danny had one potential issue on his mind that would determine the outcome of their endeavor. Investors.
Danny, our CEO, was thinking big picture. He saw a once-in-a-lifetime opportunity to start a business with someone he worked well with and was just as enthusiastic to succeed. Yet from Danny’s background, he knew it could be difficult getting investors to take a chance on a company built by two men who hadn’t known each other for very long.
“One thing I heard a lot in the early stage is investors like founding teams who have known each other for a long time. They know they get along, their personalities mesh, and they enjoy working for each other. For us, that period was us feeling that out and getting to know each other in the first place. But it is critically important.
One of the reasons businesses don’t work out, especially early on, is if founding teams have a lot of conflicts. And they end up just disbanding and going their separate ways.
There’s a real risk of that in very early businesses. Thankfully, that didn’t happen to us, but I think that was a really important period, just to get to know each other first.”
Danny Maloney, Co-Founder of Tailwind
Danny and Alex wanted to be part of the 10% of business owners who made it, which meant they couldn’t fake anything. Their partnership had to be as authentic as their concept, or they’d fall into the other 90%. Either they naturally worked well together and could show that to investors, or not.
And spoiler alert, despite those odds against them, they got their funding and became full-time Co-Founders of a brand new company that just surpassed 1,000,000 users!
Sure, most people aren’t necessarily happy in corporate jobs, but it’s a lot of effort building a new company from scratch and getting it off the ground. A person can only work that hard if they’re excited about something.
So, what were Alex and Danny so passionate about that they spent all of their free time working on this idea despite having demanding full-time jobs?
“The goal is to make the world better, solve real problems, and help people. And if we do that right, growth comes with it. But that’s really the journey, and I think a lot of the fun too. It was always about that.”
Danny
“It was very similar for me. It came down to just wanting to do something meaningful. And something that would make a difference for many people and could be really valuable. The actions, specific visions, and goals constantly changed as we learned more things. But those core aspects of it have remained the same to this day.”
ALEX
Alex and Danny didn’t want to start just any new company. They wanted to make a difference and bring value to small businesses.
“It was an obsession almost. You wake up thinking about it, and you fall asleep thinking about it. I burned my hand cooking breakfast pretty badly after picking up a pan because I was busy thinking about it.”
DANNY
Eventually, their hard work paid off. They not only got investors but were able to quit their corporate jobs, and then, Bridesview, which would later become Tailwind, was out in the world.
And how did it feel when this dream they’d tasted for so long came true? Just read this heartwarming quote from Alex and find out:
“I wanted to wake up in the morning and be excited about what I was doing. I spent six years working in finance at a large corporation doing something that wasn’t fulfilling for me. I knew I needed a change.
ALEX
And I will never forget the feeling I had the day I quit my job to start working with Danny full-time. I felt like I achieved my goal.”
As Tailwind began to take shape, Danny and Alex needed to find reliable teammates to help the company become what they envisioned. And with hiring more people, they started a journey of establishing a culture through a mix of personalities.
In the interview Danny emphasized the importance of bringing the right people onto the team and not rushing the hiring process. Danny and Alex especially didn’t want an environment like the corporate ones they came from.
They wanted to establish what felt like an extended family with individuals who cared about the quality of their jobs, as much as their leaders cared for them as human beings.
It is that family, it’s a marriage, and you want to have a good long-term relationship.”
DANNY
Tailwind treats its team members as humans first, which creates a feeling of family and loyalty.
Behind the scenes, Tailwind has channels in Slack where we “taco” (say thank you and give shoutouts) for things, and it’s common to see excerpts like this one.
The added success of our core values is due to the co-founders modeling it themselves. Their example is what carries the tradition of empathy despite the growth and changes in our team.
“For me, it came down to one thing at the core. Culture is the people you decide to put in a room together. Who did we choose to bring onto the team?
Culture’s not about any one person, despite what some people might believe. It’s not something you can dictate from the top down. You can’t create it just by hanging inspirational posters around the office.
I recognized that something magical happened when I was with others who loved their job. I think that’s what establishes great culture, because that’s when people can truly do their best work.
Amazing things happens when a group of talented, growth-oriented, and passionate people come together to strive towards a common goal.“
– ALEX
Chills. ✨
As the team expanded, the culture organically evolved.
Then, when Tailwind had a team of 10-15 people, Danny and Alex wanted to define what the company stood for.
And they ended up doing something really unique, which we’ll talk about next.
Alex and Danny knew for their company to grow they needed to provide an environment that added to people’s overall happiness.
“The way it got formalized was quite amazing. Because establishing our values as they stand today came up organically from within the team. It didn’t come from us. It came directly from the team in a company-wide discussion regarding what people loved about working here. What they valued, what was important to them. What made them happy, what fulfilled them, and what would make them successful.
Danny and I took ourselves out of it. Seeing some of it come back is how we knew we were on the right track. And we also saw how important it was for us to continue to build upon it because you could see the difference it makes at that moment.”
ALEX
Danny also had some beautiful words about why Tailwind’s culture has been so important to him as our CEO.
“Life’s too short. We don’t know how many years we get. And if I can choose a life where I love the work I do, and I love the people that I work with. I love the way we work together. We help each other grow. I can help them grow, and we all end up better at the end of that period.
I think life is a journey of growth. And the culture that we set dictates the pace of our growth. And it also dictates how much we enjoy that growth process.“
DANNY
Their dedication to team members is apparent when individuals move on. As a small start-up, several team mates were given their first chance by Tailwind.
I’m personally one of them, along with this person.
A former team member shared that when she received several job offers for a career change, Danny coached her on how to get the best offer.
Have you ever heard of a CEO doing that?
Tailwind’s culture is so successful because Danny and Alex lead by example in living and showing our values.
Growth. Bravery. Performance. Inclusion. Ownership. Transparency.
They’ve accomplished a lot together. From leaving their corporate jobs to start a business, hiring for over 50 positions, managing offices in OKC and NYC with several fully remote employees, and hitting a huge milestone of 1 million users!
Tailwind has grown from becoming the #1 Pinterest scheduler app to adding support for Instagram and Facebook. Alex and Danny built a team that has pionered new concepts like Tailwind Create, which designs visual content for our members. Essentially striving to become a complete marketing system for small businesses.
But, what are they proudest of?
“If I had to choose, I would say it comes down to the team we built and the culture we’ve established. It’s far from perfect, and we can continue to improve a lot of things. But I think that’s what I’m most proud of.”
alex
“The team is a really big part of it. Going back to the culture and why positive culture works. And being able to look back at team members who went through really fun growth curves, it was a joy to be a part of that portion of their life.
And then the other side of that, it’s not about the money. It’s about the fact that we’re bringing value to the point where our members are willing to spend their hard-earned money. For the type of small businesses we serve, we know most have tight budgets and every dollar spent matters.
And if they’re seeing enough value that they’re entrusting us, that means they’re getting value back. We’re creating value for people. We are helping them live out their dreams, the lives that they want to live. And the individual stories behind those are always so much fun to hear.”
DANNY
Danny and Alex set out to help others accomplish what they did ten years ago, and I think it’s safe to say they achieved that goal. I’m immensely grateful to be a part of such an inspiring, compassionate, and able team.
Tailwind didn’t just survive; it thrived because of the vision and leadership of our co-founders.
Interested in working for Tailwind? We’re hiring.
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