Top 10 Lessons From Season Two of Speaker Series Rewind

Here are ten key takeaways from season two of Speaker Series Rewind, our podcast featuring leading investors.

Article by
Emma Ryan

For those unfamiliar with our podcast, each week, we revisit our favorite interviews from High Alpha Speaker Series events. In Season One, we released ten episodes that featured co-founders and CEOs, including Brad Rencher from BambooHR, Matt Blumberg from Bolster, Beth Paretta from Paretta Autosports, and more. 

Season Two gave you a peek behind the curtain into the world of venture capital through conversations with leading investors from Foundry Group, Emergence Capital, Bread and Butter, and more. ⁠

Season Two consisted of ten episodes featuring:

If you’re new to the podcast and you’re not sure which episode to listen to first, below are a few key takeaways that bubbled up to the top for our team:

1. Investors Look For Founders With a “Growth Mindset”

What I look for in entrepreneurs is self-awareness. That self-awareness is key because it's a signal of a growth mindset, which in my mind is the most important indicator around whether or not you're going to be successful.
Carlotta Siniscalco, Emergence Capital Principal

Listen to the full episode here.

2. You Can Be Successful Anywhere — Not Just On The Coasts

I’ve had lots of successful companies that I’ve invested in that have been in the Bay area, but I’ve never subscribed to the notion that you need to be in a particular place. Actually, the inverse of that has been important to me, which is you choose the place you want to live and you build your life around it.
Brad Feld, Foundry Group Managing Partner

Listen to the full episode here.

3. Find Personal and Professional Alignment

It’s also so thrilling to be out of your comfort zone. That’s where we are now. Fast-forward three years later, I decided this pilot experiment was permanent and that I am deeply passionate about investing in the early stage specifically.
Mary Grove, Bread and Butter Ventures Managing Partner

Listen to the full episode here.

4. Entrepreneurial Stereotypes Are Dangerous Narratives 

Today, entrepreneur tends to mean a high-tech entrepreneur, right? Someone likely in Silicon Valley, but that’s a dangerous narrative. The prototype of a new builder describes a much broader and more diverse set of people that are starting businesses today. Again, people don’t realize this because tech is so dominated by white males. But the truth is that the fastest-growing segments of people starting businesses are women, people of color, and immigrants.
Seth Levine, Foundry Group Partner and Co-Founder

Listen to the full episode here.

5. Stay True to Who You Are, Not The Narrative You Tell Yourself

Stop doing things that you think look good for the story, and start doing the things you actually want to do. Because that's what you're going to be good at, and then more opportunities will open up.
Jenny Lefcourt, Freestyle Capital General Partner

Listen to the full episode here.

6. Having The Right Leaders Make or Break a Company — Regardless of How Great the Product Is

For me, this job is all about the people. You can have an amazing product and a large market, but if you don’t have the right team at the top that knows how to build culture and true leadership, and know how to think a number of yards down the field, to go after a very, very large outcome and vision, then you shouldn't waste your time.
Kobie Fuller, Upfront Ventures General Partner

Listen to the full episode here

7. Focus on Your Strengths, Find Teammates to Complement Your Weaknesses

If we all played the same role in the firm, the company would not be as great as it is. Luckily, we all have different perspectives. For example, one of my partners is a relationship person. I am not a relationships person but I am an ideas person. My whole career has been seeing these trends before they occur. So, I just focus on what I am good at.
Gordon Ritter, Emergence Capital Founder and General Partner

Listen to the full episode here

8. Your Culture Should Evolve as Your Company Grows

The culture at a ten person company is not the same as the culture at a hundred person company and it's not the same at a thousand person company. Global company culture evolves. You want it to evolve, right? You want cultural diversity and you want diversity of thought.
Alex Bard, Redpoint Ventures Managing Director 

Listen to the full episode here

9. Support From Investors Should Go Beyond Capital

Every investor should be trying to capitalize on what they think their strengths are.
Lisa Coca, Toyota Ventures Partner

Listen to the full episode here.

10. Start Taking Yourself Seriously

As an industry, we don't do ourselves any favors by talking about ourselves as startups. If you have $1 revenue from somebody you don't know, you're no longer a startup. That's not something you should wear on your arm and be proud of. The minute you have one customer that is not somebody you know, you are a business.
Paul Singh, Bump Health Co-Founder and Chief Strategy Officer

Listen to the full episode here

You can also stay up to date on the latest episodes of Speaker Series Rewind by subscribing to the podcast wherever else you like to listen.  You can find us on Apple PodcastsSpotify, Google Podcasts, and Stitcher.

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