Last updated on May 13, 2022 - My Free Marketing newsletter 👀
Recently, on our 12th Sumo team retreat in Tulum, Mexico, I sat down with my co-founder and CTO, Chad Boyda. We reflected on his entrepreneurial journey and the lessons he’s learned along the way.
Growing up, Chad dreamed of being an entrepreneur. But it didn’t work out for him like you see in the movies or read on TechCrunch.
Chad has been building businesses since he was 16 and shared a ton of INCREDIBLE insights during our conversation, including:
I’ve known Chad for a long time (we worked together for nearly 10 years). Even knowing him for years, I learned crazy new insights from our discussion.
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Before starting Sumo, Chad created a number of startups.
Chad’s biggest learning experience — and startup failure — was a company he built with his own money, plus money from friends. With the capital, Chad and his team spent a year building products.
The first problem: Chad and his team assumed people would need these products. They did no validation on the product before they started building.
After pushing the product to the public, Chad heard crickets. The product wasn’t solving anyone's pain point.
When the capital ran out (a year after launch), Chad was making payroll on his own personal credit cards to make sure people got paid. This led to over $100,000 of personal debt. It took Chad 10 years to pay off this debt.
10 years of paying off credit card debt from a failed startup is a lesson you don't forget. Chad learned many things from this experience, but had one major takeaway
“We built upright without caring about what people actually wanted.”
Customers should be central to product development. No matter what you’re working on, validate your idea with customers, get their feedback, and iterate.
Customers don't always know what they want, but it's important to test your assumptions before you invest too much time or cash into something.
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Growth happens when you step outside of your comfort zone. But most people don’t want to rock the boat:
To be successful, you have to embrace difficult conversations.
One New Year's Eve, Chad challenged himself to have AS MANY uncomfortable conversations during the year as possible.
He wanted to talk about things that made him nervous, and share outside his comfort zone.
The “embrace difficult conversations” resolution was the best resolution Chad ever did. The skills he developed have turned out to be incredibly important throughout his life and career.
Without being able to embrace tough discussions — plus the mindset that comes with it — Sumo wouldn’t be the 8-figure company it is today.
If you tend to avoid uncomfortable situations, how do you get started? How do you learn to love discomfort?
Chad’s advice is to start small.
Having uncomfortable conversations doesn’t mean you have to act like a dick. It just means you’re truthful and honest with yourself.
These types of conversations can be awkward, but they’re great stepping stones to feeling confident embracing difficult situations.
Next time you feel nervous about asking a question or approaching a conversation, embrace the nerves and just do it.
Taking feedback and moving into action is an incredibly valuable set of traits.
It's tough for many of us. How often do we use feedback to better ourselves?
Many people hear feedback, get nervous, and repress it. “That’s not true” or “I don’t need to change,” we say.
If you think this way, you're missing out. If someone is willing to have a difficult conversation with you and share open, honest feedback it’s usually because they care and want to help you improve.
My friend Neville and I have had TONS of heated debates, but ultimately things get hot because we both want each other to grow.
Once you’ve received feedback, how do you use it to fuel personal growth and self-improvement?
It may not seem like much, but staying aware of what you need to work on can make a huge difference in your personal and professional success.
As entrepreneurs, we like to think we blaze our own paths. But, that's ignorant. There’s so much we can learn from others.
Learning is one of the driving factors behind my podcast:
As a 16-year-old, Chad graduated high school early and decided against going to college.
Chad’s a strong believer in education, but he was bored of what he was learning. He wanted to pursue his own education on his terms.
So, Chad set out to build his own companies. He experienced some small successes, and was feeling good about his decision to go from high school to full-time work...
But then the dotcom crash happened and shit hit the fan.
When the future looked bleak, Chad shifted his strategy:
“I had been working for myself and building businesses all these years with no idea what I was doing. I thought I should learn how other people do it.”
Chad started working for other entrepreneurs who taught him a TON about building products, A/B testing, marketing, pricing strategies, and more.
By becoming an employee and opening himself up to learning, Chad elevated himself into a better position to succeed as an entrepreneur.
Don’t let your ego get in the way of learning.
You might want to be an entrepreneur and have “founder” in your Twitter bio, but there’s nothing wrong with taking a step to the side in order to learn and improve your skillset first.
Most of my readers want three things:
It doesn’t happen overnight. All success starts with baby steps.
Becoming successful starts with creating a vision for success.
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Once the vision is clear, you can take small, calculated steps.
Over time, each of these small steps will add up to make a huge difference in your life.
At Sumo, we have the concept of “1% ideas.” Every week we aim to get 1% better at something. Over a year, these changes compound to massive improvement.
Imagine in your own business:
Don’t be blinded by the big picture. Think about how you can break down the journey into small, manageable steps.
Most importantly, start moving towards your goal. Don’t sit still.
“You don’t always have the right answer.”
I thought I wanted a fast, sexy-AF sports car. I was wrong.
I thought people would pay to remove Sumo branding from their site. I was wrong.
I thought I would work at Facebook forever. I was wrong.
The lesson here? It’s okay to not always have the right answer. The important thing is to constantly test and experiment with your assumptions.
At Sumo, we’ve changed our pricing seven times in the past two years (!!!). We’re going to keep experimenting to find our sweet spot.
Without testing, you’re leaving a whole bunch of opportunity on the table:
You can’t answer questions like these without testing.
This approach also translates well into like outside of business. I’ve been using my “Test Shit Out Strategy” to optimize my happiness and figure out what’s really important to me before I commit.
Always be testing.
For more about failing in a business until you eventually succeed — and lessons learned along the way — listen to my full conversation with Chad.
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