Rob Dyrdek likes to say he was “raised by entrepreneurial wolves.” Lately, he’s been imparting advice to young Bruins.
Dyrdek, a serial entrepreneur, venture investor and media mogul, began his career as a professional skateboarder at the age of 16. Just two years later, he started his first company — and never looked back. In the nearly three decades since, he’s helped create dozens of businesses, built a media empire that has made him a fixture on TV for a generation and mentored countless young entrepreneurs through his philanthropic ventures, including the Do-Or-Dier Visionary Foundation. That long and winding entrepreneurial road led to the creation of the Dyrdek Machine, a Los Angeles-based venture studio that has already seen exits totaling more than $450 million since its founding in 2016.
Just prior to the pandemic, Dyrdek joined the Venture Accelerator at UCLA Anderson as an advisor. He takes part in the Accelerator’s semiannual Showcase, has served as the premiere guest on the Accelerate podcast, has hosted several Venture Accelerator company founders on his own popular business podcast, Build with Rob, and in early 2022 held a fireside chat at Anderson about scaling startups.
Dyrdek offered his top tips for the newest Accelerator cohort — and all entrepreneurs tapping the resources of UCLA Anderson’s Price Center for Entrepreneurship & Innovation.
1. Define your vision
“When you start with a vision, it should be super narrow. You want to take the time to get extraordinarily clear, do a ton of self-evaluation and really define it. You want to find simplicity on the far side of complexity. But know when you set out to realize that vision, it’s going to continue to reveal itself. What it actually takes to realize that vision and how that vision is going to evolve and change and get more dynamic over time are going to be incredibly exciting and incredibly motivating — but if you do it right, it’s still going to be the same vision you had at the beginning.”
2. Expect struggles
“When you start and grow a company for the first time, it can be painful. You’re responsible for so much, you don’t even know what you’re responsible for because you’re learning how much you have to do on the fly. Maybe you’ve raised a little bit of money. Maybe you start generating enough revenue to hire. You’re still going to ask yourself, ‘Are we ready to hire?’ Even if that hire could drive the company further, it’s a struggle to make that decision. All I can say is ... embrace it.”
3. Make your business easier to run over time
“As an entrepreneur, your goal should not be working 18 hours a day. I hear so many early-stage entrepreneurs say, ‘Let’s just keep grinding it out!’ That is not the goal when you build a business. Instead, you want to grow it in a way that you can begin to hire the right people, and design, automate and optimize the systems to get a higher output from your business with less effort. Why? So that you can actually enjoy running your business.”
4. Design the day
“A lot of people will say, ‘If you win your morning, you can win your day.’ And that’s true. But if you design your day, you can win your life. Understand that mastering your time is going to give you the balance you seek and give you the peace of mind that you’re searching for. You’ll be able to fit in all the things you need to feel energetic and feel great, because you’re doing it with purpose. It starts with designing the day in chunks and saying, ‘Here are the things I’m going to commit to and here’s when I’m going to commit to them.’”
5. Fail small
“Everybody talks about learning from failure. But I also learn deeply from success. Even though something might work, you also see, ‘Wow, if we had done this, this and this, then it really would’ve worked.’ Failure is just the more painful side of learning lessons. You want to get to a place where you’re micro-failing all the time, not macro-failing. When you’ve tried an idea and it goes completely bust, that’s the most painful way of learning. But as a business, along the journey, if you’re failing left and right in small ways, you can make those pivots and adjust and take your idea to the next level. That is the joy of it, you get to continually evolve and grow.”
6. Hire someone to do the hiring
“As you begin to scale, focus on hiring the one person who’s going to hire everybody else. Spending all that time and energy to find that person who understands the vision, understands you, understands the mindset and skill sets needed, is going to make them the person on the front line recruiting everyone else, interviewing everyone else. If you make sure that one hire is the one you do not miss on, by the time people get to you, they’re vetted so perfectly — boom, you’re on to the next one and on to the next one.”
7. Doing new things is scary — embrace them
“In business and in life, there are all these aspects of doing something for the first time that make it really difficult. While you go through the process, it begins to get easier over time. I think if you can take the time to realize that and set your own personal expectations every time you do something new, there is going to be a process of learning, evolving and growing — until it gets past a certain point where it finds a rhythm, where it feels more natural and organic and you can enjoy it.”