3 days ago
Entrepreneurship: It's Not All About Success—It's Also About Having Fun
Vivek Bhaskaran is founder & CEO of QuestionPro, a global leader in survey and research, data and insights services.
When people think about an entrepreneur's legacy, what most often comes to mind is the flashy exit they made, the quarterly board meetings (thankfully, I don't have to deal with those) and whatever they're planning to do after their current big thing. But I'd argue it's not about any of that. It's about the wild ride itself and the people who are with you—the moments when you're laughing so hard at your own audacity that you forget you're supposed to be stressed about burn rates and market penetration.
After building QuestionPro from zero to where we are today, I've learned something that most business schools will never teach you: The legacy isn't the valuation—it's the stories your team tells at the bar five years later. It's whether people genuinely miss working with you and want to work with you again, or if they're just sucking up on LinkedIn.
We're all so obsessed with being the next unicorn that we forget to enjoy building the darn thing. I see entrepreneurs grinding themselves into the ground chasing the PE money, the valuation and the fame, instead of building the experience that actually matters to your employees and to, most importantly, your customers.
Who are the entrepreneurs I respect? They've figured out that sustainable success comes from creating an environment where people genuinely want to show up, not because they have to but because they're curious about what crazy stuff we're going to pull off today. They've mastered something that's both simple and incredibly difficult: making the journey itself irresistible.
Most companies treat success like checking a box—send an email, maybe mention it in the next all-hands meeting and move on. That's lazy celebration culture at its finest. When we hit our $10 million revenue milestone at QuestionPro, we didn't just announce it. We took the entire company to Thailand. And not just the leadership team—everyone. When we blew past goals in 2021, everyone in the entire company got a bonus— everyone, whether their role had bonuses associated with it or not.
Why? Because these moments become part of your company's DNA. New hires hear these stories during onboarding. Veterans share them during tough quarters. They're proof that success isn't just acknowledged; it's celebrated like it actually matters.
Building a culture of celebration and boldness doesn't require a massive budget; it requires creativity and a willingness to look ridiculous. Being frugal isn't something that people should be ashamed of; frugality can lead to the wildest innovations. Some of our most talked-about company moments have cost virtually nothing but generated enormous cultural value. Take our 'Rickshaw Challenge': Instead of expensive team-building retreats, we organized rickshaw races through SFO during Dreamforce. It was epic. Now, getting the rickshaw imported from India is a whole other experience that's become its own piece of QuestionPro folklore.
The goal isn't to spend money on fun—it's to demonstrate that your company values creativity, spontaneity and shared experiences. When employees see leadership willing to be playful and take calculated risks, it gives them permission to bring that same energy to their work. This translates directly into more innovative problem-solving, better collaboration and the kind of workplace energy that makes people excited about Monday mornings.
It might be easy to say this as the boss, but very few of these ideas and activities have been mine! What we've done is give key team members discretionary spending authority with one simple rule: Don't ask permission, just make it happen. Whether it's our annual customer conferences or surprise and delight for a long-time customer, giving your leaders budgetary freedom and responsibility to create an experience demonstrates trust at the highest level. When you give someone budget authority without requiring approval, you're not just delegating tasks. You're delegating judgment. You're saying, 'I trust you to make decisions that align with our values and goals.' This level of empowerment creates an ownership mentality faster than any equity package or performance bonus. It also generates the kind of creative solutions and customer experiences that you could never have mandated from the top down. Let your team run a little wild, and you also might end up with a live Texas Longhorn or a Grammy award-winning singer at your next event.
The PR and media might remember all the companies you bought, sold, built, failed at and succeeded at, but real legacy is something you can't control. When teammates move on and life continues, the stories, experiences and folklore are what people will be talking about years later.
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