The Mysterious VC

The world of investing, specifically venture capital (VC), can be opaque and intimidating. Lots of acronyms, insider vocab, and websites with general terms like vision, tech, or support.

If you’re a founder, startup leader, or aspiring investor who wants to learn more about VCs, how do you get started in learning things like:

• How do VCs think?
• What do they care about?
• What are differences among investors in personality and strategy?
• How do they like to work with people?
• What are their pet peeves?
• What business ideas or markets are they excited about?

Good news! No mind-reading necessary. VCs are sharing their inner thoughts all over the internet.

By regularly reviewing some great blogs and podcasts, you can start to understand the wide range of personalities and philosophies, as well as the similarities.

6 Ways to Get Inside a VC's Head

1. All-In Podcast

Jason Calacanis hosts David Sacks, David Friedberg, Chamath Palihapitiya each week in my favorite podcast in the VC and investing space!

• 4 super smart, successful investors who are “besties”
• 4 different perspectives on investing strategies and world views
• Lots of heckling and jokes
• Many innovative or non-mainstream opinions
• Discussions of current events and market conditions

I’m exposed to new concepts and perspectives every week!

2. Both Sides of The Table

I’ve been reading this blog by Mark Suster, Partner at Upfront Ventures, for over a decade.

Mark is candid, funny, specific, and opinionated! He regularly and boldly advocates for underrepresented groups which I love.

He shares specific scenarios, email language to use, and shines the light on unspoken assumptions or rules of the VC world.

A few good ones to get you started:

• How To Ask For Help, Favors, and Intros
• What You Should Send Your VC Before a Meeting
• How Much You Should Raise in Your VC Round? And What is a VC Looking at in Your Model?
• Why Confidence Is So Important In Fundraising

3. AVC

Fred Wilson, Managing Director at Union Square Ventures, publishes a bite-size post several times a week on this great blog. He shares a reasonable, calm, long-term perspective on many investment and life topics.

A few examples of the diversity:

• Employee Equity: How Much? - one of the top articles on this topic
• Competing To Win Deals - inside look at VCs
• Swapping NFTs - call for founders
• A Range Anxiety Weekend - personal story with innovation opportunity
• New Leadership at Tech:NYC - New York community news

It’s interesting to compare Fred and Mark. Very successful VCs with wildly different styles. They each care passionately about entrepreneurs but have varied investing philosophies, market interests, and personal priorities.

4. 20 Minute VC

Harry Stebbings interviews a different VC in each podcast episode. With several episodes per week, that’s a lot of VC exposure in a short time! David Friedberg was a recent fascinating one.

The Memo is a sub-category of the pod that dives into the “why” of an early investment in companies like Pinterest, Snapchat, and Doordash.

Find out:

• What investors looked for
• What gave investors conviction
• What the risks and unknowns were
• Fun stories from the early days

5. Invest Like The Best

Patrick O’Shaughnessy interviews different types of investors including VCs on his podcast. Learning about non-VC investors is helpful in understanding the broader ecosystem.

For example:

• Jenny Lefcourt is a 20-year investor and entrepreneur sharing what markets excite her (elder-focused tech, future of work, low-code/no-code) and what she looks for when investing.
• Jenny Johnson is CEO and President of the one of the world’s largest asset managers, Franklin Templeton, overseeing $1.5 trillion dollars.

Both investors named Jenny, wildly different stories!

6. Venture Deals

A classic book by Brad Feld and Jason Mendelson on VC deals, terms, motivations, legalese, and more.

It explains:

• What terms VCs care about and why
• Where to negotiate
• What to let go of
• What signals you’ll be sending (good and bad)

It’s incredibly helpful if you’re going to be fundraising or negotiating term sheets! It’s very specific so if you’re not there yet, start with the others.

VCs Revealed!

1. VCs are more transparent than you think. VCs candidly share what they care about, how to work with them, and how they invest. Get the inside scoop through blogs, podcasts, Twitter, LinkedIn, books, recordings, and more.

2. Each VC is different. Job titles look similar but VCs are very different! Learn the various personalities, leadership styles, and investment strategies with common themes around success.

3. VCs are human! They have good days, bad days, personal stress, intra-firm politics, quirks, egos, strengths, and weaknesses. They make mistakes, great decisions, and get lucky. It’s easy to create a mystique about them or put them on a pedestal.

The reality is – VCs are smart folks who know their industry. Just like you.

What other VC blogs, podcasts, books, and resources do you enjoy? Do they help you understand the inter-workings of the VC brain? What remains a mystery?