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From Professional Violinist to Experienced Founder: Caroline Winnett on The Power in Purpose

The Crunchbase “Female Leader Series” is comprised of stories, Q&As and thought-leadership pieces from glass-ceiling-smashers who overcame the odds and are now leading successful companies.


Caroline Winnett is the executive director of the Berkeley SkyDeck, a global hub for entrepreneurship, and one of the leading accelerators in the world. 

She launched the Berkeley SkyDeck Fund, a VC fund investing in SkyDeck startups that shares half of the fund with UC Berkeley. She is a serial entrepreneur, civic activist, angel investor, adviser and board member of several startups, as well as a frequent speaker on startups, accelerators, women in business and consumer neuroscience. Winnett received her MBA from Haas School. Her undergraduate studies were at Brown University and she earned her violin performance degree at the Indiana University School of Music.

In this Q&A, Winnett shares her tips for improving your sales pitch when speaking with investors, and explains why finding a mentor isn’t just important—it’s essential to your success as an entrepreneur. 

 

Q: What is one challenge you’ve found as a female leader, and what advice would you give to other female leaders or founders in a similar situation?

Starting a company isn’t easy. From the outside, it looks glamorous. The media have almost fetishized entrepreneurship.

The reality is different. In the beginning, you’re doing the jobs of five other people. Starting a company requires you to be a lawyer, engineer, human resources expert, marketer and analyst. The earliest years are a constant juggling act, where you can’t drop any balls. The days are long, the work is grueling and the pressure is immense.

A supportive partner, can also help lighten the load. Just as you wear many hats in your day-to-day work, they can help in other ways. They can be your daycare worker, therapist, cleaner, cook, taxi, courier and more. When I say a supportive partner, I don’t merely mean someone who will pick up the slack while you’re burning the midnight oil. I’m talking about someone who understands the pressures of being a founder. A person who will take care of you during the most challenging years of your life in the hope of a better future together and the potential to create something that changes the world.

Entrepreneurship isn’t just hard on the founders. It’s hard on the spouses and partners of founders, too. They have to deal with the tight household budgets, the burden of childcare, long workdays and periods apart while you visit investors and partners in other countries. A supportive partner will persevere through this period with you and keep your ship afloat.

 

Q: You used to be a professional violinist. How did this experience help you transition into a founder?

So many successful founders have nontraditional backgrounds. A CompSci degree or an MBA is no longer a prerequisite to launching your own successful company.

The soft skills that matter in life—discipline, perseverance and focus—can be fostered in many ways. My professional music career began at a conservatory. These are hugely competitive places. Hundreds of talented applicants fight for the same position. Only the most dedicated, self-sacrificing musicians win.

My teen years and early 20s were spent ignoring distractions and forgoing social events so I could practice. I was single-minded in my determination to become a successful violinist. This discipline served me well when I later applied for business school.

I wasn’t afraid to be assertive, and risks didn’t scare me. Musicians take them all the time—it’s the nature of the job. Think about it: Spending your teenage years focused on one thing, just for the 1-in-200- chance you’ll win a coveted spot at a conservatory.

 

Q: Can you share three tips for improving your sales pitch when speaking with investors?

Let’s start with the most obvious one: practice. This is something musicians know well. Before a big performance, they’ll spend months and weeks rehearsing, turning elaborate orchestral pieces into muscle memories that can be activated on instinct. Treat your sales pitch like that. Script. Think. Rehearse. Record yourself delivering your pitch and watch it. Test your pitch with friends and family and ask for their honest feedback. Always look for opportunities to polish and improve.

Here’s the great thing about practice: When you know something cold, there’s less room for anxiety or nerves. It feels natural when you know your pitch inside and out, even memorizing the cadence of your speech and when to inflect for emphasis. You’re simply doing something you’ve already done a hundred times before. So, why would you feel nervous? Well you do, but you will have a better shot at framing your nerves as excitement. If you tell yourself “I’m not nervous, I’m excited” and you have thoroughly practiced and know your pitch cold, you can get into a positive frame of mind. Try it. It works.

Next, it’s essential to have a long-term view. Don’t be afraid to be audacious. Show your investors the “big world domination plan.” Talk boldly about how you’ll reshape the industry and demolish competitors.

One of the most prominent mistakes early-stage startups make when seeking investments is focusing on their specific industry niche or the modest accomplishments they’ve made. Investors want to see huge potential for exponential growth.

When an investor backs a company, they’re making a bet. They know nine-out-of-10 companies they invest in will fail. The one that succeeds will recoup the losses from the other nine and deliver a healthy profit. That means they’re instinctively looking for ambitious, expansionist companies that aren’t afraid to take risks in pursuing growth.

Finally, keep the dialog going. Delivering your pitch is the easier part. The tricky bit is maintaining investor interest. Keep them excited and interested. Maintain lines of communication.

 

Q: What is the main lesson you have learned as a business leader about building a sales community? What are the most important things to look for?

Excitement matters. It’s contagious. If you’re enthusiastic about your product and have a crystal-clear vision for how it’ll change the world, others will share it. People have an intuitive ability to detect bullshit. It’s obvious when someone is simply selling an idea to get a paycheck.

Make sure whoever sells your product shares your excitement and vision. Don’t hire anyone who doesn’t. A good sales community won’t just evangelize your product, they’ll listen to your customers. They’ll understand their needs and provide invaluable feedback about how your product can evolve to meet them.

Remember how I said early-stage founders wear many hats? As your company grows, you’ll take less of an active role in the sales process. You’ll hire people for that. Your involvement will shift to a managerial one, ensuring they understand the product and the customer. While you may not be selling to customers anymore, you should always keep an ear to the ground.

 

Q: What qualities have led to your success?

It’s those same soft skills I talked about earlier. Grit, determination and discipline. The ability to power through challenging months when the days are long, and you don’t have enough money to pay yourself.

These skills can be developed anywhere—I learned to play the violin, for example. Decades spent practicing, and learning to play entire compositions by memory flawlessly, taught me that I can accomplish anything if I put in the hours.

I’ve completed an Ironman marathon and many 100-mile bike rides. These taught me to ignore the discomfort and keep moving toward the goal, no matter how much my thighs ache or how tired I feel.

Anyone can be disciplined. And you don’t have to think about it as punishment or a form of asceticism, where you torture yourself for some future goal. By being disciplined, I was able to balance my time and work more effectively, allowing me to spend precious time with my young family during the early stages of my company. I’m not saying it was easy. But it was far more manageable because of discipline.

 

Q: Do you think mentorships are important as a founder? How do founders find good, reliable mentors?

Entrepreneurship is a lonely game. Finding a mentor isn’t just important — it’s essential to your success.

It’s easy to forget how much serendipity plays into business success. Chance encounters are often the determining factor behind failing or thriving. 

Mentors effectively stack the deck in favor of their mentees—they understand the landscape and have the relationships. They can introduce you to potential new hires and investors. In essence, they lessen the need for luck.

But here’s the thing: Mentors don’t advertise themselves as such. Nobody will email you out of the blue and offer to spend their time, pro bono, helping you. You’ve got to look for them actively. That’s the bad news. But here’s the good news: They can be found.

Join a community. Network. Meet people. Build relationships. Look for in-person events in your city. Get active on Twitter. For better or worse, it’s the virtual water cooler of the startup world. Twitter is where introductions are made and exciting conversations take place.

Eventually, you will find someone whose experience you’ll come to trust and depend upon.

 

Q: What is the premise behind Berkeley SkyDeck? What sets it apart from other accelerators?

The University of California, Berkeley has a storied history in the technology space. Its alumni include the founders of Apple, Intel, Tesla and Sun Microsystems. It’s hard to think of a university with a more significant impact on the technology landscape. It’s where the earliest work on RISC processors, which now power our smartphones and IoT devices, took place. It’s where BSD, which forms the basis of macOS and iOS, was developed. As such, it’s a logical place to start a global entrepreneurship hub. And I’m just scratching the surface.

Through our alumni network, not to mention our faculty, we’re able to make the introductions that can lead to business success. And about 1,800 Berkeley students attend our intern fairs each year looking for internships with our startups. This access to talent is something other accelerators can’t replicate.

We offer an attractive support package to our cohort of companies. This includes $200,000 in investment, 1-to-1 support, highly-curated content and the equivalent of $750,000 in free or discounted resources.

And, like a musical conservatory, places are highly sought after. We accept less than 2% of the companies that apply. To date, over 1,000 startups have gone through the SkyDeck program, and collectively they have raised over $1.4 billion.

We’ve begun to expand SkyDeck, opening a European location in Milan, Italy. This offers many of the same benefits of the original SkyDeck program but with a laser focus on the European market, which presents founders with different challenges and opportunities than Silicon Valley. We’re proud to have recently announced Batch 15 along with new tracks led by prestigious and renowned advisers and corporates. 

 

Q: What’s the main lesson you’ve learned since joining Berkeley SkyDeck?

In Silicon valley it can be seen as a good thing to drop out of college for your startup. Much is made of Bill Gates, Steve Jobs and Mark Zuckerberg, all of whom dropped out. Peter Thiel notably offers a package of investment to young founders, the $100,000 Thiel Fellowship, on the proviso they defer or drop out of university. And yet, joining a university gives a great sense of community. Students gain mission and purpose. They bring strangers from across the world together, expanding their social networks in ways that will prove helpful later inr life. These attributes are hugely important for business success.

There’s power in purpose. If a founder can clearly communicate their vision to employees and investors, they are more likely to succeed. Traditional education is where you can identify and catalyze the things that matter to you. It’s where you learn what you’re most passionate about.

 

Q: What are the most important things you look for when bringing on new cohorts?

Products matter. It’s basic, but the three “w’s often inform investment decisions.” 

  1. What problem does this solve? 
  2. Who is it for? 
  3. Why is it the right time to start this business?

Passion, drive and determination are all critical—vital soft skills we look for in founders. But they are no substitute for the fundamentals. We want the whole package—a great team and product balanced with a meaningful path to success.

  • Originally published September 9, 2022