Cayla Weisberg #TAKEHEARTTRIBE

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Cayla Weisberg
These are fears I live with everyday — I can buy into them, or I can recognize that they are there and let them be exactly what they are: fears. Nothing more. Cayla Weisberg

Cayla Weisberg is a Partner at InvestHER Ventures, an early stage investment firm that partners with and invests in female entrepreneurs.

As a familiar face in the Chicago startup community, Cayla has built a track record for scaling startups and providing a voice for women in tech. She is focused on sourcing strong female founders with technology enabled solutions for large markets. 

Cayla’s enthusiasm for entrepreneurship began young, having launched a concierge shopping business at 17 years old. At 19, she joined forces with a fashion wholesaler, winning the business of national retail conglomerates throughout undergrad. Post grad, Cayla worked for one of Fortune’s “100 Fastest-Growing Companies” as assistant director, achieving record breaking sales performance for three consecutive years. Following this success, she transitioned into the startup ecosystem, leading business development initiatives for two fast-growing tech companies at a venture capital incubator.

Having built a plug-and-play sales roadmap throughout her career, Cayla offers hands-on thought leadership on start-up scaling, pivoting & operational excellence for InvestHER’s portfolio companies.

CAYLA, WHAT IS YOUR GREATEST FEAR?
What they don’t teach you about fear is that the more you stretch yourself — the more you have to lose. In my life, I have declared unreasonable goals to myself, my family, and my community. With these declarations, my commitment is my word: to actually do what I say I’ll do… and this is a heavy load to carry. Will my companies actually exit for hundreds of millions? Will I actually change the face of venture capital for women? Will my career come to a screeching halt once I have my baby? What example will this set for the thousands of women in the Midwestern tech community? Am I a good wife? Will I even be a good Mom? These are fears I live with everyday — I can buy into them, or I can recognize that they are there and let them be exactly what they are: fears. Nothing more.

WHAT EXCITES YOU THE MOST ABOUT ATTENDING THE FEAR PARADOX SUMMIT?
Now, more than ever, it is crucial for women to band together and get real about what’s holding us back, so that we can unlock our potential. Our community will only get stronger this way. I am so excited for the fear-inducing experiments during the summit because we don’t see opportunities everyday that challenge ourselves to get out of our comfort zone. Bring it on.

WHAT DO YOU HOPE TO LEAVE WITH?
I cannot wait to witness the immediate breakthroughs and eventual outcomes that I’m expecting out of myself and my community of powerhouse women.

WE LOVE HOW YOU ARE PLAYING A BIG ROLE BY PAVING A NEW PATH IN VENTURE CAPITAL AND HAVE SEEN ALL THE WORK YOU ARE DOING WITH STARTUP FOUNDERS ACROSS THE US. WOULD YOU AGREE THAT EDUCATED RISK-TAKING IS THE CORE OF ENTREPRENEURSHIP?

Do you find that there are risks or fears that founders often have that hold them back from reaching that next “milestone” with their company? I absolutely believe that calculated risk taking is a must in order for entrepreneurs to be successful. With that said, it doesn’t come overnight. Educated risk-taking is like a mastering delicate recipe. Like delicious dishes, not all startups are created equal- which is certainly the case when it comes to preparation and execution. Chefs need to come to the kitchen prepared with list of ingredients and steps to prepare the meal, just like entrepreneurs need a playbook and business plan. We all know that even if you follow a recipe line by line, things most often don’t go as planned. This is where gut instinct and labor intensity come into play. It is only with experience and mastery of uncertainty that these factors become second nature. The more we talk about skill and will, the more we will become able and willing to conquer the most difficult milestones.

CALCULATED RISK IS A HUGE PART OF YOUR WORK – IF YOU COULD ANTICIPATE WHAT ROLE FEAR MIGHT PLAY IN THE NEXT FIVE YEARS, HOW DO YOU CALCULATE THAT AND WHAT ARE YOU DOING TO MITIGATE FEAR THAT MIGHT IMPEDE ON OPPORTUNITIES?
One thing I have learned over the past year as a VC is the skill of quantifying risk. I make it a practice to notice my fear, and then inspect it. In the process of breaking the fear down, I have been able to associate a level of risk toward my worry with a metric. If my concern is around investing in a company, for example, instead of jumping into the feeling of doubt, I dissect each component: market size, team, product, scalability, price of the deal, etc. This helps me get clear with where I see the risk, and the opportunities that may outweigh my fear. In the next five years, I plan on using these tactics at a much greater scale to tackle bigger opportunities.


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