"10 Cheat Codes I Learned While Scaling to $400M ARR" with Yext and Roam Founder Howard Lerman
"10 Cheat Codes I Learned While Scaling to $400M ARR" with Yext and Roam Founder Howard Lerman
"Teddy Roosevelt, the previous U.S. President, suggests the 5-minute meeting. As president, his secretary would set a timer, and he would hold 5-minute meetings."
All of the ten cheat codes below might sound ridiculous, but they’re all tricks Yext and Roam founder Howard Lerman stole from non-tech people who were geniuses in their field. These cheat codes are tactical, unconventional wisdom that helped scale Yext to $400M.
#1: Memorize Your Lines
Many people talk about how to tell your story as a company. You have to be a grandmaster storyteller. Nailing this skill is the most important thing you can do. That advice alone isn’t anything new, so how do you actually become a master storyteller of your vision?
John Lennon once said whenever he would write a song, he wouldn’t write it down. He encouraged the other Beatles to do the same. Why? Because you’ll know it’s a good song if you return to it a day later and still remember it.
When you’re crafting your story, memorize your lines. Being able to recall it later forces you to craft a more compelling story, like a poem. Repeating the same thing and getting into a rap-like rhythm around it is a formulaic process in storytelling.
So, memorize your lines and learn them by heart until your message is as clear and succinct as “She Loves Me” by the Beatles.
#2: The Live Demo is a Worthwhile Risk
Live demos are highly underrated. They’re super risky and nerve-wracking because every time you do a live presentation, there’s a chance the Wifi won’t work, or the AV will be subpar. Everything goes wrong when you plug your computer in, but you have to take the risk and do live demos.
When you go up on stage like Howard did for TechCrunch in 2009 to do a live demo, everyone knows you’re taking a huge risk, and everyone is taking that risk with you. Everyone wants to see what will happen next because they know you could fail.
That’s the live demo. Of course, the risk is all about the environment and not the product. If something breaks, that’s ok. You get sympathy points for trying it anyway.
#3: 1:1 Meetings are Terrible
”I think all meetings are terrible, and I especially have it out for 1:1 meetings,” Howard says. In 2014 or ‘15, he wrote a LinkedIn post saying so, and every proper manager in the world said it must be terrible to work for him and that he was ignoring basic management principles.
Why does he hate one-on-one meetings?
When trying to make things happen as fast as possible, having 30 scheduled one-on-one meetings with your direct reports means your entire schedule will be full of meetings – it’s a terrible idea and clogs your calendar.
If you schedule a meeting, people tend to queue up their issues, even if they’re urgent, slowing everything down.
1:1 meetings tend to become therapy sessions to air out grievances.
You’re trying to start a company and take over the world, so you must get stuff done and move on. It’s time to cancel the 1:1 meetings with your team. That doesn’t mean they don’t talk to you. It just means it’s not scheduled, and things are handled quickly.
#4: Tim Cook and Sunday Night Meetings
Howard holds Sunday night executive meetings. When starting a company, everything that could go wrong will go wrong, and even more things you didn’t anticipate will go wrong.
Sunday night meetings are the best hack to stay on top of this because you get ahead of the work week and hit the ground running with your team on Monday. The founders who are starting the company, and are trying to do the impossible, should be available for an hour and a half to plan the week. Usually, hestarts at 8 p.m. Sunday night.
Make it a part of your routine. Tim Cook does it, too. The meeting doesn’t have to be video, either. You can be on a call and figure out what you’ll do for the week, and on Monday, everyone goes after their priorities.
#5: Opt for Advisor-Led Growth
Dan D’Aniello founded the Carlyle Group, a huge P.E. firm. He also happened to be Howard’s neighbor when Dan was first starting the company, and Howard was around eight years old. After Dan became wildly successful, Howard was in college and called Dan to pick his brain.
He noticed they added James Baker, former U.S. Secretary of State, as an advisor to the Carlyle Group. Howard asked Dan about the choice, to which Dan said James Baker was a phone call away from anywhere in the world, and he wanted to tap into that.
Let’s tie this story back to SaaS. If you think about the BDR/SDR outbound model, it’s inverted. When running Yext, Howard received so many crappy gifts he didn’t want as an attempt to secure a meeting with him. There’s empathy for BDRs, but the bottom-up model, isn’t a good model.
You want to take your cap table and use it as a weapon. Take all the stock options you have and think about who your target audience is. Instead of investing heavily in BDRs, SDRs, and outbound to generate demand, use your stock options to bring on advisors who can make a fast introduction to the top people and immediately get you in.
A word of advice: Make the stock only vest up to one year. Don’t make it four years. When you hire employees, it’s four years, but you use up all your connections in six months.
#6: Teddy Roosevelt and the 5-Minute Meeting
Teddy Roosevelt, the previous U.S. President, suggests the 5-minute meeting. As president, his secretary would set a timer, and he would hold 5-minute meetings. If he can make decisions in matters of national consequence within that time frame, anyone can do it.
Try it, if you like. Create 5-minute slots. You’ll be shocked that most people will finish within three minutes because it forces you to quickly get to the point instead of trying to fill a 30-60-minute meeting.
#7: If You Ever Have a Bad Day, Meet with Customers
Jim Steel, the president of Salesforce, says, “I’ve never had a bad day with customers.” They’ll cheer you up, so get on a plane and meet with them. Jim told Howard that when Marc Benioff hired him to found the Enterprise group at Salesforce, Marc used to tell Jim to get out of the office if he saw him in there.
“I have found a direct correlation in the Enterprise for the amount of time I see a rep in the office and how bad they are,” Howard says. You’ll never see your best reps because they’re with customers.
#8: Bill Campbell and the Board Chair
Intuit once considered buying Yext 10-12 years before going public. Howard got to know Bill Campbell before he passed. When they met, Bill showed up talking like a sports coach. Why does that matter? If you’re a founder and CEO at your company, you shouldn’t also be a chairman. Instead, that title should go to someone amazing who can open doors like Bill Campbell.
Make them Chair of the board. They have no power, only calling the meeting to order, but if you’re a Series A company or earlier, you want this next-stratosphere person. In those earlier days, the board structure usually consists of two founders and the VC. The VC has preferential voting rights, and seeing this incredible person interested in the company is a positive signal for them.
Not only that, but you’ve basically bought yourself an extra board seat because later on, Bill will be in your corner. It’s a no-brainer. Howard did this at Yext and Roam.
#9: Do Not Delegate
Every piece of advice you’ll receive as you scale will tell you that you need to delegate. Do not delegate. Here’s the thing. You have to delegate functions, but there’s an order to it.
First, it’s legal. That’s easy. Then, accounting, HR, and strategic finance. After that, operations, demand gen, sales, engineering, and storytelling. The second to last thing to delegate is recruiting.
Over your dead body should you delegate product market fit, Howard says. Your job as a founder is to own and dominate product market fit completely. You can’t hire someone to figure out product-market fit with customers. This is the single most important thing you can do.
The core essence of being a founder is finding, holding, and hugging product market fit and never letting it go, no matter how many products you launch.
#10: Have Fun. It’s Your Company
Remember, nobody knows anything. This is your opportunity at this moment in time to have a playhouse. It’s your company, so you can do things your way. People can tell you what works for them but don’t do it if it doesn’t feel right for you.
Your company is an extension of what works for you. Founder is the only permanent title, even as your company gets big and goes public. You might step back as CEO, but you’re the founder forever.
So, construct it your way, and never let anyone tell you how to do it against your gut because everything has to come out of your gut. When Apple made the iPhone, they didn’t make a better phone. They reinvented the entire retail experience.
Tesla reinvented how you buy a car. It’s different, and they did it their way. When you make your product, you can reinvent other parts of your business like admin, GTM, and anything else. You don’t have to follow any playbooks on sales or marketing. Make your company your own creative canvas.