Jeremy Goldberg is the President & Quarterback of LeagueApps and oversees all marketing, business development, investor relations and people operations. He is also an Operating Partner at 212MEDIA, a venture development firm.

One of my favorite parts of my job is spending time with sports organizers. I’m inspired by their hard work, the value they add in their communities and I love to hear their dreams for their organizations: new facilities, new locations, new staff, new programs. As a founder myself, their challenges are familiar: staffing, capital, cash flow, culture and more.  

As LeagueApps approaches the milestones of more than one billion dollars processed on the platform and growing our team to more than 80 people this year, we wanted to share with our community some lessons we’ve learned from scaling LeagueApps.

1) Stay in business long enough to figure out how you’re going to make money

“Everyone has a plan until they get punched in the mouth.” That’s a famous Mike Tyson quote and one I think applies well to running a business. Whatever idea you have for how to build your business is invariably different from what will actually work — the key is staying in business long enough to figure it out. It’s about surviving, and adapting, until you uncover what the market needs and how you can make money solving it.  

LeagueApps actually came out of another product: Sportsvite, a recreational sports network aimed at helping players, teams and organizations find their sports community. We reached hundreds of thousands of people, but competing for sports advertising dollars was difficult. Still, our core idea was right, here was a need for better tools for sports organizing and community discovery.  We noticed the “super users” of our site, sports organizations trying to find players, had something else in common: they all needed better technology. That was our lightbulb moment — LeagueApps was born. The path we took gave us insights and helped us focus on what are now our product’s greatest strengths: flexibility and usability.

It will always take longer than you think to figure out how to translate your idea into an organization that is sustainable and thriving. Anticipate that, and be smart about how much you spend in the early days of your organization. Be agile like an athlete: listen for signals, adjust your strategy and welcome change.

2) Define your values and culture early — and explicitly

We’ve spent time with leaders of some of the largest tech companies in the world and we’ve seen a pattern in their advice: the difference between good companies and great companies comes down to culture, which influenced the people they hire, develop and keep.  

We took this advice to heart, and when we were a four-person company, we set out to define who we were. We asked each other, our early partners, our investors and advisors:  What was it like to work with LeagueApps? How would we describe our most successful team members?

We saw similar responses, and identified the core values already evident in how we were building the company.  We came up with an easy way to remember them: SPORTSDoG: Sportsmanship, Passion, Openness, Results, Team, Student of the Game, Difference Maker, and Grit. We then put those values in front of us all the time — literally, by posting them on our office wall and figuratively, using them to evaluate and train new hires. We also give out regular awards tied to specific values.  

Know what you stand for early on, stay true to it. This will help you build and align your team and guide decisions as you scale.

3) Seek outside advice, especially on areas you don’t know

Scaling an organization is hard, and full of x factors. Surround yourself with people outside your organization who can offer experience and guidance. Having informal mentors or even paid advisors will force you to get out of the day-to-day, and can accelerate your learning. This can be a mix of people who know your business well — and people from other sectors who bring specific experience in an area: management, finance, marketing and the like.

We can look around LeagueApps and see the impact of external advice. There’s the flash financials tool Jim helped us develop for real-time visibility into financial performance and projections; the product process Brian trained our team on that helps ensure we’re building the right features at the right time; and the management techniques we learned from Joe to get the most out of our team. We regularly post questions to a listserv of other tech companies seeking recommendations and introductions.

Find peers you admire and set up a monthly call to exchange ideas. Identify other business leaders you respect and learn how their success might translate to lessons for your business.

4) Create playbooks to track wins, losses and lessons

Paul, one of our early investors who had run a multi-billion organization challenged us early on:  “Winning in business is not about trying to be the best. It’s about being the best at getting better every day.”  

We had plenty of success, and failures, and more failures, to learn from. The key is keeping track of those lessons so we could learn from them. We create playbooks for every part of the business — from how to talk about our product, to our launch process, to how to run an offsite meeting. We use Google Slides to track versions, share comments, and make our playbooks accessible to our whole team.  

Playbooks help you to look back at things you’ve tried, identify where processes may no longer work, and manage transitions.

5) Embrace the hard things

Scaling a business is hard. If it was easy, someone else would have solved the problem and the opportunity wouldn’t exist, but there it is, in front of you. Be leery of shortcuts and easy answers. Recognize that you create the most long-term value when you do things that are hard — tasks that require grit, sweat, and perseverance.  

Reid Hoffman, the prolific entrepreneur and early Facebook investor who led PayPal, founded LinkedIn, put it best:  “To scale, you need to do things that don’t scale.”  

When you jump in, roll up your sleeves and do things to grow your business that seem impossible, you’ll discover how to grow and how to be scrappy. You are also creating a barrier to entry because most aren’t willing to do that same hard work. In our case, that meant a willingness to reach out to grassroots organizers directly and personalize the service we deliver.

Bonus Lesson:  Never stop learning

We’re reminded of the adage about parenting: As soon as you think you have it figured out, everything will change. One guarantee about scaling your business — you’ll constantly face new challenges because what worked before likely won’t work with continued growth. You’ll need to develop new playbooks and surround yourself with new people. You’ll also get through those challenges by staying true to your values and culture, and not being afraid to be gritty.  

Best of all, enjoy the journey.  We’re so appreciative of the experiences we’ve had, and the team we’ve done it with, and are excited for what’s ahead.

Resources:

A few great resources on scaling businesses that helped us:

• The Hard Things about Hard Things by Ben Horowitz
• Scaling Up:  How a Few Companies Make It…and Why The Rest Don’t by Verne Harnish
• Reid Hoffman’s “Master of Scale” Podcast
• First Round Review Blog

We want to hear your tips on how you’re scaling your organization.

Are there books you are reading? Podcasts you are listening to? Share them with me directly at JeremyG@leagueapps.com and we’ll share them back with our community