“Being a founder is really hard”

Being a founder is really hard. There are some challenges that only other founders can understand. And then there are other challenges unique to your business that no one else will understand. An important step for modern founders is to treat mental health as an integral factor as important as physical health. It’s never too soon to find a therapist in whom you trust and can confide and who can help make you the best leader you can be.

Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles.

Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup.

I had the pleasure of interviewing Ran Craycraft.

Ran Craycraft is the Managing Partner and co-founder of Wildebeest, a hands-on digital agency for innovative brands. With over two decades of experience building award-winning products and brands, Craycraft has helped elevate teams at General Electric, NBC, AOL, General Motors, Toyota, Google, Microsoft, Hulu, Snap, Coca-Cola, Frito-Lay, and more. Ran is actively involved in the Silicon Beach startup scene and is a proud alumnus of DAAP and Newhouse.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

For sure! I got my career jump-started with NBC in Rockefeller Center. I was an unpaid intern working odd jobs off-hours to make ends meet while living in New York. I worked in the promos department and when an urgent video editing need came up while several folks were on vacation, I got the opportunity to sit down in a big boy chair and put my film degree to work.

After several years at NBC in a variety of increasingly digital roles, I became a producer in the Digital Innovation department, tasked with crafting complementary products and brands for NBC properties like Heroes, The Today Show, America’s Got Talent, and more. I made the move to the West Coast with AOL to lead the Entertainment division and took the reins of internet fossils Moviefone, Sessions, and Winamp. An opportunity came up with a Swedish agency I really admired to launch their US division with a focus on building their product and entertainment portfolio. Here, I was able to get my feet wet in advertising, and I soon saw an opportunity to construct a more balanced creative agency that equally values strategy, tech, and design–and that’s how Wildebeest was born.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

When I was working with my first advertising agency, I was surprised by how the creative stakeholders called all of the shots. Whether or not a concept made business sense for the client or was technically salient, it didn’t matter; as long as the concept was sound and it could win an award, we did it. Focusing on such short-sighted client engagements was a bit off-putting for me. Instead, I chose to build a consultancy that understands brands have business needs, too, and that clever solutions that align strategy with design and technology can give them a competitive advantage.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

When I was sixteen, my mom made it clear that I needed to get a job to help out with bills. I landed a job as a server at Pizza Hut for exactly one day–one glorious Saturday. I had to show up at what seemed like sunrise for a teenager and sat in the walk-in freezer for hours, prying apart frozen pizza dough disks and placing them in their signature cast iron pans. It was mind-numbing. I eventually got to start waiting tables around 10 a.m. (sidenote: who goes to Pizza Hut at 10 a.m.?) and after a couple of hours, I had only made about a dollar in coins.

While I stood at the counter waiting for customers, a bitchin’ red truck peeled into our Appalachian Pizza Hut parking lot blasting Def Leppard, and a handsome young man and woman danced out in their swimsuits and started spraying water on our restaurant’s windows. My eyes were the size of frozen pizza dough disks as I asked my manager if I should go stop them.

She told me, “No, that’s Dirk McDougal. He washes our windows on Saturdays.” And then five minutes later, Dirk and his golden tan come in and give a wink and a nod to my manager who responds with twenty bucks. Shortly after the door closed behind him, I left my red apron on the counter and started my first company, a window-washing business! Now while this wasn’t directly how Wildebeest started, this was the nudge I needed as a kid to understand it was possible to make a very good living doing something you enjoy.

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

We stand out because we’re so small. So many of our contemporaries measure success in headcount and that’s never been a motivator for us. My partner and I love getting in the trenches with our clients and helping them solve problems one project at a time. If I owned a brand that needed an agency, I would want to make sure I get the attention of the most seasoned professionals, not just the junior folks at a mega-agency who happen to be available at the time.

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

I know more than a few agency leaders who question the intrinsic value their advertising campaigns for big brands bring to the world. I get it. In fact, I’ve felt that way, too. This is why my team makes it a point to find a balance in the work we do that combines giant brands, causes we believe in, and promising entrepreneurs with big ideas. Ultimately, we feel it’s healthier for our business and, frankly, more fun to keep us honest. When we were all working in-office, my partner and I would make it a point to celebrate our company’s birthday each year by inviting our entire team to volunteer in our community. We worked at animal shelters, delivered meals to people in need, and built websites for nonprofits that needed an update.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Stubborn. Bootstrapping a creative agency doesn’t make a lot of financial sense. From the early, low-paying projects, high contractor expenses, to helping launch then wave goodbye to the businesses of tomorrow, it takes a stubborn, laser-focused, masochist to keep doing this and try to do better each time.
  2. Loyal. There have been a lot of opportunities to cut ties whether with teammates or clients in favor of getting a little ahead. That’s just not who we are. Being a loyal business leader and consultant means always having the best interest of our employees and clients in mind–because you’ll never know when you’ll need them in your corner.
  3. Fiercely Independent. If it weren’t for my innate yearning to make an impact and do something different, I think my life would be a lot easier. I often tell young entrepreneurs that if there’s anyone in the world you’d like to work for, do everything you can to seek them out and offer your services. Because being an entrepreneur is hard, it’s often thankless, and frankly, there’s an excellent chance it will fail. If you have the ability to work at a big company with a stable job and decent salary, do it ten times out of ten.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

The worst business advice I ever received was probably to “get it in writing”. Just because you have a contract doesn’t mean it can or will be enforced. When you’re working with national or global partners across state lines, enforcing a breach as a small business against a recognized brand is virtually impossible. When multiple jurisdictions are involved, it gets hairy and very expensive for a small business to litigate. Instead, know your risk, know who you’re planning to do business with, and if anything seems suspicious about a deal, pull out. Always have a plan B.

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

When we were first getting started in the business, we took on a project from a client who falsely represented their role at their company. This person didn’t have the right to sign for their company and had ulterior motives in soliciting business with us. When he got our signed contract and invoice, he used my signature and company information to forge loan applications and successfully took out a lot of money in our company’s name. The details and end result of this story are for another day, but this was an enormous challenge for our young company to overcome. We had a combination of a steadfast team, loyal clients, and unrelenting determination to help us get out from under this and rebuild our company.

Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

We’ve seen more than our fair share of challenges in the years since we started our company. We’ve gotten into a cadence where it seems each year, we go head-to-head with a new Titanic struggle. The drive we have to surmount each new challenge is our strength in acknowledging everything we’ve already overcome. Being an entrepreneur is a rollercoaster–you will have the time of your life, may scream at the top of your lungs, and you will definitely feel your stomach in your throat.

The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

Don’t get comfortable. When things feel like they’re finally right and you’re firing on all cylinders, this is when you need to grow. Founders can be hunters or they can be gatherers. It’s important to be on the same page with your co-founders to know how you’re all going to contribute. In some cases, a hunter can compliment a gatherer. However, in other cases where you need a more aggressive plan, everyone needs to be hunting–that is, being proactive in growing your company rather than becoming complacent with what you find laying around.

Let’s imagine that a young founder comes to you and asks for your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

It’s easy to answer this one by asking if “you need it?” but after seeing the difference between startups with unlimited funds and bootstrapped ones, I think the better answer here is asking about the socioeconomic status of your network. If you or your family have a high net worth, then absolutely raise some money and surround yourself with a heavy-hitting team. If you don’t happen to own a real estate conglomerate or rideshare service, then consider starting with enough seed money to get you to profitability. Prove out your business model and then use your progress to raise the money you need to scale around the concepts you’ve proven.

Ok super. Here is the main question of our interview. Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”? If you can, please share a story or an example for each.

  1. Be a goldfish: For those ‘Ted Lasso’ fans out there, you know what I mean. Great things are going to happen to your business and so will some terrible ones. Never get so excited or defeated by any one turn of events to make you lose sight of your goals. When something great happens, celebrate it and move on. When something terrible happens, understand why and then move on.
  2. Assemble and empower your village: You are the passion behind your business. It wouldn’t exist without you and when you’re getting started, there is no one who can do a better job than you. However, it’s your mission as the founder to comprise the strongest village you can and empower each of them to use their unique experience and talents to solve problems. If you find yourself too in the weeds, constantly solving problems for your village, it’s time for some changes. I worked with a startup founder who believed his experience and intellect were superior to that of his team. The result of this was a team that operated in fear of missteps with an emperor wearing no clothes.
  3. Disable cruise control: If you’re not growing, you’re shrinking. When everything feels right and the pieces you’ve assembled are finally all making sense together, it’s time to shake things up. Take big steps and don’t let your team or processes get complacent. You might as well ask the dealership to just rip out cruise control completely so you can have complete control of your speed, faster or slower when and where you need it.
  4. Find ways to measure progress: Your unique business’s progress isn’t always directly measured by revenue or daily active users. Examine your business and find the metrics you can keep an eye on and track progress. Maybe NPS makes sense for you. Or maybe a unique ratio of revenue to DAU divided by revenue per user. Airtable is a great tool you can use to track data points from several different sources and write formulas to measure their change over time.
  5. Never be afraid to blow it all up: Remember that your company is not the same as your software. Your company is your people, your processes, your data, your ideas. Your software is a collection of code that connects you with your customers. Never be afraid to blow up any part of your business, especially your software, if it means progress. In the early dotcom days, it was a CEO’s worst nightmare to have to rebuild their software in a few years. This is probably the biggest procedural change in the last twenty years. If you’re not constantly blowing up your software and reimagining it in a more efficient, scalable, and secure way, you’re on cruise control (in which case, refer to number 3).

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

  1. Waiting too long to launch. There’s been a lot of progress in founders’ understanding of MVPs over the last five or so years. However, there’s still room for improvement. Many founders are so afraid of failure that they put their heads down and plow forward according to plan regardless of results. It can be devastating for a startup to spend all or most of their war chest getting to launch only to find there were some assumptions that didn’t pass muster. Instead, it’s advised to launch with a product that has several different assumptions implemented that you can measure. Then after some traction, react to those results and relaunch accordingly.
  2. Leading by “gut feeling.” There’s nothing worse than working for someone leading a business by gut feeling. As crazy as it sounds, this is more common than you would think. While your gut may get you launched, it’s an impossible task for your growing team to buy into your vision and scale your business without being able to get inside your, well…gut. Ensure your team understands what drives your business, and empower them to find creative ways to succeed.
  3. Measuring success by headcount. 2020 slowed this thinking quite a bit. However, there are whispers of “look how big our virtual team is now” that will likely lead to some new lessons learned. Pre-pandemic, outgrowing your office and moving into a converted warehouse with exposed beams and polished concrete floors were all the rage. Now, teams are growing virtually and facing new challenges with payroll taxes, work-life balance, childcare, recruiting, employment law, and scheduling. Startup success will look different in 2022 and it won’t likely be measured by your headcount.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

  • There’s no honor in being exhausted from late hours in front of your team. Your enthusiasm and healthy lifestyle will be infectious to your team. While 8+ hours may not always be possible, do your best to sleep well each night–maybe with the help of a new mattress or melatonin.
  • Don’t eat like a monster. Be sure to take a lunch break and steer clear of any foods that might zap your afternoon energy. Especially as you enter your thirties and forties, you start to realize how much your diet impacts your brain health. I like to put a thirty-minute recurring lunch break on my calendar to ensure unexpected meetings don’t leave me on ‘empty’ when the afternoon marathon meetings hit.
  • Be sure your office setup keeps your eye and back health in mind. Start with an office chair that offers back support and is adjustable to your optimal desk height. Preventing eye strain is another huge factor. Set your display to turn on Night Shift and warm up your monitor’s color spectrum–this will help your eyes not have to work as hard to read text.
  • Being a founder is really hard. There are some challenges that only other founders can understand. And then there are other challenges unique to your business that no one else will understand. An important step for modern founders is to treat mental health as an integral factor as important as physical health. It’s never too soon to find a therapist in whom you trust and can confide and who can help make you the best leader you can be.
  • Some founders have no issues getting up early and running a few miles or hitting the gym. I’m not one of them. I’ve found it easier to stay physically active by joining a league or a club that uses peer pressure to keep you engaged. It’s much harder to skip when it means you’re letting your team down. Another perk of a league is networking–helping you to soft-sell team members and clients while staying healthy.

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 would like to have a better way for all of us to discover and support independent causes and movements that matter. We all hear about the big causes and when Facebook decides I should hear about the small ones, I guess I do. But wouldn’t it be cool to have a highly personalized discovery engine to find and fund highly specialized causes that need your help?

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

I’m inspired by the community work NFL star, Andrew Whitworth, has done in two of my favorite cities, Cincinnati and Los Angeles over the years. He pulled more than his weight helping causes and small businesses throughout the pandemic while putting an exclamation point on his NFL playing career.

How can our readers further follow your work online?

You can follow us on Twitter, our newsletter, or Linkedin.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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