Kristin Westberg

Where were you in life when you decided to start The Rev Collective?

I believe in the saying, “Every cloud has a silver lining.” When I decided to start my business, I was in the middle of one of the most challenging seasons of my life. I was going through a divorce, and my 6-year-old son was starting Kindergarten, navigating his own social and emotional challenges. It felt like everything was happening at once, and starting a business wasn’t part of any plan I had.

The opportunity arose unexpectedly when the company I was running as CEO had to suspend operations due to legal and financial difficulties faced by its owner—completely unrelated to the business itself. What seemed like the worst possible timing actually opened a door. I was able to take that moment of upheaval and start fresh with the remaining clients and team members who were still with me.

It hasn’t been easy, but I’m learning to embrace what feels like a complete life makeover. While the circumstances were difficult, they pushed me onto a path that now feels full of possibility, and I couldn’t be more optimistic about the future.

What resources would you recommend to someone starting a business?

First and foremost, for someone starting a business today, I can’t overstate the value of having a group of trusted advisors. These are the people I turn to when I’m stuck or unsure—whether it’s a big strategic decision or just needing perspective during a tough moment. Their support has been a lifeline more times than I can count.

Second, having a team you trust makes a world of difference. I’ve been fortunate to work with individuals whose skills and integrity I deeply respect. Knowing you have people who will show up and deliver is incredibly grounding, especially when everything else feels uncertain.

And lastly, technology has been a huge help. I’m always looking for ways to work smarter, not harder, and the right tools can make such a difference. AI tools, in particular, have been game-changers for me, but I’ll be the first to admit there’s still a learning curve.

Starting a business is a daunting journey. I’m constantly learning and leaning on these resources to keep moving forward—and I try to remind myself that it’s okay not to have all the answers.

Do you have any fears that keep you up at night?

One fear that keeps me up at night is the possibility of failure as an entrepreneur. Starting my own company earlier this year has been one of the most terrifying—and exhilarating—things I’ve ever done. Every day, I wrestle with doubts about whether I’m going to succeed.

I took a significant risk by investing all my resources to build a new service line focused on sales training and coaching, something I feel deeply passionate about. It’s a business I’m building entirely from scratch. In doing so, I walked away from a different service that had a steady stream of clients and predictable demand because, ultimately, that work didn’t fulfill me in the same way.

Some nights, I question that decision. Did I let go of the safer, less fulfilling path too soon? Should I have stayed with what was working, even if it didn’t light me up? Despite those doubts, I’ve made a commitment to myself to see this through. I remind myself that the risk is worth it because I’m pursuing work that truly aligns with my values.

While the fear of failure is real, it’s also a motivator. It pushes me to show up every day and give my best. I know this journey won’t be easy, but I also know that it’s where I’m meant to be.

What is your personal motto?

My personal motto is inspired by a quote a friend recently shared with me: “Courage is regret insurance.” I remind myself of this daily. It’s a powerful reminder not to let fear drive my decisions but to stay true to a path that aligns with my goals and dreams.

I once attended a workshop where we were asked to consider what we’d want written in our epitaph. At this stage in my life, that question resonates deeply. It pushes me to reflect on the legacy I want to leave and how I want to be remembered.

I try to use those reflections as a compass, guiding my decisions and actions. For me, it’s about living with intention and purpose, knowing that the courage I show today will shape the impact I leave behind.

What does success look like for you?

Success has meant different things to me throughout the various chapters of my life. Early on, it was about recognition and status—earning validation and building a name for myself. Over time, it evolved into a focus on performance and results, driven by achieving measurable milestones.

Now, success has taken on a more personal, holistic meaning. At this stage in my life, my professional and personal successes are deeply intertwined. I view success as the ability to show up as my best self—in my actions, in my relationships, and in how I contribute to the world.

For me, success is going to bed each night knowing I did my best, acted with integrity, and lived with purpose. It’s about being fulfilled, enriched, and aligned with the values that matter most to me.

In the moments of self-doubt or adversity, how do you build yourself back up?

Self-doubt is something I navigate regularly—it’s pervasive and often feels like an uninvited companion in moments of adversity. In those times, I remind myself to pause and ask, “What’s the worst that can happen?” This question helps me examine risks in a healthy, grounded way, rather than letting fear take over.

Recently, I worked with a coach who helped me uncover a powerful truth: the more we can tolerate moments of extreme discomfort—whether it’s embarrassment, failure, regret, or any other challenging emotion—the more resilient we become. If we’re willing to feel those things and move through them, we start to realize that they don’t have to hold us back.

For me, building myself back up means leaning into that discomfort, knowing it’s temporary and that it’s a necessary step toward growth. The idea that I can handle whatever comes my way has been transformative. It’s not about eliminating fear or doubt but learning to coexist with them and not letting them stop me.

Kristin Westberg is a Sales Transformation Leader at her company The Rev Collective, where she works directly with founders and CEOs to modernize their sales approach and design scalable solutions to fuel profitable growth.