We had the pleasure of hosting Rinky Sethi, CISO & Chas Larios, CMO from Upwind Security - one of the most dynamic players in the cloud security space today.
In this episode, we talk about what it actually takes to build a successful startup in 2026, and how Upwind is using community as a real strategic advantage. Together, they share practical insights on authenticity, growth, and standing out in a crowded market.
What stood out across the conversation is that success in startups today has less to do with polish or hype, and more to do with being real, staying close to the problem, and building strong relationships.
Authenticity matters more than messaging
Startups that are honest in how they communicate tend to build stronger trust over time. People can tell when something is forced or overly polished. The companies that stand out are the ones that feel consistent in how they show up, internally and externally.
That same idea applies inside the team. When people are open about what’s working and what isn’t, it creates a healthier environment where ideas move faster and people collaborate more naturally.
Focus on the problem, not the solution
A strong theme from the discussion is the importance of staying focused on the problem rather than getting attached to a solution.
Startups that do well tend to stay flexible. They’re willing to change how they solve something, as long as they stay committed to solving the right problem. That mindset makes it easier to adapt when things change.
Not all problems are worth solving
There’s a big difference between something that’s “nice to have” and something that actually hurts when it’s not solved.
The companies that break through are usually solving problems that force action, problems where people can’t just ignore the issue or stick with the status quo. If the problem isn’t painful enough, nothing else really matters.
A different approach to cybersecurity marketing
Cybersecurity has traditionally leaned on fear to get attention. That’s starting to change.
Upwind’s approach is more about making things approachable and human:
- Clear product experience and design
- A brand that feels less intimidating
- Community-led engagement instead of one-way marketing
- Using data and signals to guide outreach
The goal is to make cybersecurity feel less like a black box and more like something people can actually engage with.
Community is becoming a real advantage
One of the strongest points in the conversation is how much weight community now carries.
Instead of treating customers as just users or leads, companies like Upwind are building relationships through events, conversations, and shared experiences. That creates trust and feedback that you don’t get from traditional marketing.
Curiosity and trust shape how teams work
Curiosity keeps teams learning and trying new things instead of getting stuck in routine. Trust allows people to take risks without second-guessing every decision.
When both are present, teams move faster and work better together.
Hiring for how people think, not just what they know
In fast-growing companies, experience matters but mindset matters more.
The people who tend to succeed are:
- Curious
- Comfortable figuring things out
- Able to handle uncertainty
- Willing to take ownership
They don’t just follow processes they help shape them.
Finding the balance between speed and structure
Early-stage companies often win by moving quickly and staying flexible. But as they grow, they need some structure to keep things from falling apart.
The challenge is adding just enough process to support growth, without slowing down what made the company work in the first place.
Final thought
Across everything discussed, a few things stand out clearly.
The companies that do well are the ones that stay close to real problems, build genuine relationships, and don’t lose their sense of honesty as they grow.
Everything else tends to follow from there.
If this sparked ideas or questions, feel free to reach out. We’d love to hear from you and keep the conversation going.