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6 Lessons on Life and Fundraising

Jason Yeh
September 3, 2021

6 lessons to use while raising millions in venture capital...or in everyday life 

In my podcast Funded, we tell the crazy stories of what founders had to go through to raise money for their companies. At the end of every episode, there is a debrief with my producer Olivia, who does not come from a startup or investing background. The outsider perspective is refreshing and as we rehash key insights, she often remarks that she might be able to apply some of the fundraising lessons into her own life.

This is not strange to me at all. While focusing all my energy on helping entrepreneurs understand how to raise money, there are many things I always refer to that sound more like general life lessons than tips on how to land millions in venture capital. Here are 6 important concepts that may help you in your daily life as well as in the pursuit of investment dollars.

In pitch decks and in life, the journey is the destination

I often get pushback from founders around spending time building pitch decks. The reasons vary (I don’t have time, I do better without a deck, no one’s asked me for one yet, etc.), but no matter what they say, I’m always quick to share how valuable the process of building and refining a pitch deck is. 

In my opinion, the process is just as valuable as the end result.

Working on a pitch deck forces you to confront what are the most important parts of the business to you, why you’re building this business, and how you’re going to be successful. Stripping out all extraneous detail is essential to creating the most effective deck possible and doing so can shine a light on deficiencies in the business that need to be addressed before you can successfully raise money. Iterating towards a great deck is one of those classic “slow down to speed up” moments that I try to force on founders.

That cliché of “the journey is the destination” is more often applied to life in general than it is in pitch decks but it never clicked with me until I applied it to my fundraising frameworks. In situations where you have an end goal in mind, appreciate and respect the journey to get there - it often has as much if not more value than the destination itself. 

Lose vs. Learn

In podcast interviews, emotional stories provide some of the best tape. It’s why I often ask guests of Funded, “do you have any horror stories from your fundraise?” I know all founders have been rejected and that there are usually painful stories behind those rejections.

When I interviewed the founder of Levels, his answer was “not really.” Don’t be misled; that answer didn’t reflect a lack of rejection while fundraising. In fact, it was quite the opposite. He had over 500 pitches that didn’t end with an investment. The difference was how he framed rejection in his head. To him, rejection was pointed feedback and an opportunity to get better.

That’s what you should think rejection is in fundraising and in life. This is not to say rejection isn’t painful. It is. But, if you can see the opportunity beyond the rejection, that pain can be a short stop on the way to a much better place.

Be authentic

One concept in startup investing that founders hear often is “bet on the jockey, not the horse”. That concept is easy to nod along and agree with but harder to fully internalize without seeing a string of startup successes and failures. Because of that, I spend extra time on this with founders. I make sure they go a step further to highlight their authentic self and its connection to the business when pitching.

The strongest example of this I’ve seen is with Topper Luciani, Founder/CEO of the online thrift store Goodfair. I interviewed Topper and learned about his path to raising $5MM as an industry outsider. In the beginning, his reaction to early rejections was to change who he was and match what he thought the venture capital industry wanted him to be by wearing suits or button-down shirts in meetings. When he finally embraced his authentic self, wearing head-to-toe thrifted clothing (and not the fancy kind), is when Imaginary Ventures saw him as the founder they had been searching for to lead a business dedicated to recycled clothing.

You’ve heard this one since you were a little kid, and it turns out it still applies as an adult trying to raise millions of dollars. Be yourself. Know who you are and embrace it. Realize that the point is to find people who think your authentic self is special. If you go through life trying to change in reaction to people that don’t matter, you risk missing those who were searching for you all along.

Be chased

When founders start fundraising for the first time, there is an understandable awe and anxiety around the process. That makes sense. Asking for millions of dollars to accelerate a company you care deeply about is a big deal. These sometimes crushing feelings are even more prevalent in BIPOC and other underrepresented founders because of societal pressures.

This completely natural feeling can lead to some of the most damaging behavior within a fundraise. When founders start chasing investment, they create the perception that they’re desperate and no one wants to invest. In so much of investing, perception is reality so following this mindset creates a self-fulfilling prophecy. In other words, those fundraises are essentially DOA.

Part of the reason repeat entrepreneurs and founders that come from privilege have an easier time raising is that they believe they deserve to be funded. They embrace a hard to internalize truth within entrepreneurship: Founders do not ask for money. Founders OFFER a valuable and limited opportunity to invest.

This lesson is all about confidence and self-belief. Whether you are pursuing venture capital funding, asking someone out on a date, or applying for a new job, remind yourself that you’re great and it’s an opportunity for them. People will believe if you believe. Be chased. 

Shoot your shot (ask!)

For 30+ years I had a really hard time asking for help. A combination of imposter syndrome (If I ask they’ll know I don’t belong), fear of rejection/failure (getting told ‘no’ will be the worst thing ever), stubborn pride (I should be able to figure this out), and my Asian upbringing (model minorities never rock the boat) held me back from getting to where I knew I wanted to be.

With many founders I work with, it’s not uncommon to see some or all 4 especially when they begin fundraising. This is something I work on fighting past as soon as possible. Fundraising is difficult already without handicapping yourself by not accessing all the help you can get...and I feel the same way about life!

Asks can short circuit long learning cycles and unlock doors to great success. They can connect you with amazing people and help you avoid catastrophic pitfalls.

In fundraising and in life, the willingness to ask for help is the ultimate cheat code. Everyone should be using it.  

Build a Meaningful Network. Anyone can.

So many things to say about networks and networking but I’ll try to keep it short.

First: no one wins on their own no matter what hero stories you read in the media. There are families, communities, and networks all conspiring to make successful people successful. Internalize this reality and begin to make building your network a priority.

Second: some people have advantages but anyone can build a meaningful network. Be kind to people, support others, and live with integrity. With those guiding principles, you will naturally build a meaningful network through the normal course of life.

Last (for now): when building a more targeted network, realize that people and industries that feel far away are likely closer than you think. One strategy for accomplishing this is finding people who are in the networks of the people you want to meet but are easier to get to. For instance, maybe you went to the same school as someone who works for a person you’d like to talk to. Start with the initial person you have the alumni connection with before finding how to connect to your ultimate goal.

And, while this is an incredibly important lesson in startup fundraising, it is also an essential life lesson. It’s the reason Laura Del Becarro from Sora told me she has been committed to diversity in everything she does professionally. From hiring engineers while at Mixpanel to building her cap table for her startup Sora, giving back means contributing to diverse networks so that societal advantages don’t keep accruing to the majority.

Build a meaningful network and help others build theirs, anyone can.

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