Winning in Tech Without Losing Your Soul
Winning in Tech Without Losing Your Soul
How can business owners create a culture that values winning?
I hate to lose—it drives me crazy. This is actually one of my interview questions because I want to know if others share that same passion. Everyone loves to win, but for me, losing is especially hard. It keeps me up at night, replaying the details. I’ve passed that drive on to my son, who plays basketball and hates losing as much as I do.
I try to surround myself with people who have that same passion for winning and a deep dislike of losing, whether it’s my business partners, my wife, or my top employees. If they’re okay with losing and just see it as a “learning opportunity” without feeling the drive to do better, something’s missing.
What factors should business owners consider when taking growth risks?
You need to think about what you want to accomplish. If you’re okay with a lifestyle business, keep doing what you’re doing—no need to take big risks. But if you want to scale, you have to take some risks, depending on your comfort level and timing.
Ask yourself: if you took the risk and failed, could you start over and be okay? If yes, go for it. If failing means a serious setback, consider it more carefully. And when you take risks, partner with people who balance you out. For instance, my partner acts as a counterbalance, making sure we have cash reserves in case things go wrong.
If both partners are highly risk-tolerant, that can lead to trouble, as cash flow could run out. But if both are overly risk-averse, growth will be limited. Some of the wealthiest people I know took fewer risks and succeeded steadily over decades. Decide on the approach that’s right for you.
What key decisions can drive business growth through calculated risks?
We took risks for the first time. The Mitchell Group, especially with Jeff being more risk-averse, had been cautious. For us at Higher Cloud, a few key decisions marked our commitment to growth. First, we asked a long-time employee of the Mitchell Group to move from Arizona to LA. She was crucial for accounting, finance, and administration, and we needed her experience and trustworthiness in our office.
Second, we decided to open a new, beautifully designed office. We invested more than ever before, focusing on hiring quality talent and taking on challenges we previously would have avoided. We took risks on people—even if we weren’t entirely sure they’d work out—and committed to a five-year lease, knowing it was a gamble. From relocating a valuable employee to signing long-term agreements, Higher Cloud's foundation was built on risk and decisive action.
How can entrepreneurs align success with personal values and family goals?
For me, business is something I enjoy, but my true “why” is my family. My goal is to provide a great life for my kids and wife, eventually passing down a legacy that makes a meaningful impact. The more success I achieve, the more I can give back to the world.
I invest in tech startups and advise various companies, helping them grow. I also donate to causes I believe in, like children’s charities and organizations that uplift the community. Beyond family, I’ve always wanted to succeed in business. Competing in the business world is like a continuation of sports—there’s no limit to how far you can go, whether as an individual or a company.
How can business owners prioritize family events in addition to work commitments?
You have to let people know that you want to be part of everything important, but there will be times you’ll miss certain things. I’m intentional about choosing what I prioritize. If it’s a school or sporting event, I’m there. I set the expectation that I’ll always show up for the big moments and will be at other events when possible, as long as it doesn’t interfere with our family’s success. My family needs to know they come first.
Balancing work and family is tough. Sometimes you choose work not because it’s more important but because it requires your attention. I don’t have all the answers, but I’m learning. One thing I’ve improved is focusing entirely on my family when I’m with them. I haven’t necessarily spent more time with them, but I’m more present. This small shift has made a positive difference.
What is the value of having diverse perspectives about risk-taking?
Alone, I would take certain risks without hesitation. But with a family, it’s a different level of responsibility—it’s not just about me anymore.
My business partner, who is more risk-averse, brings balance to our work. Similarly, my wife, who is also risk-averse, balances me at home. She’s not interested in luxuries or extravagant trips; she enjoys a calm, simple life. Her perspective reminds me that we don’t need more, and sometimes I realize she’s right. That balance is important. I wouldn’t take major risks now because the responsibilities I have extend beyond myself. I’m fortunate and content with what I have, so taking on big risks wouldn’t be worth it. At this stage, I’m focused on making a bigger impact without putting my family at risk.
*This interview has been edited and condensed for clarity.*
