Charlie O’Donnell sat down to chat over coffee about the biggest secret to cultivating a successful career: investing in serendipity. This idea of investing in serendipity is the opposite of most career and personal branding advice where every meeting, interaction and social posting should be goal driven and intentional.
Charlie is a general partner and investor at Brooklyn Bridge Ventures. He manages $30 million across 3 separate funds where he invests this money in pre-seed and seed companies. Which basically means he invests in baby or brand new companies. What sets him apart: He will talk to you PRE-PRODUCT and PRE-DECK with NO WARM INTRO.
Social media creates opportunity, whether you know it or not. Therefore investing time into social media is investing into your own serendipity. The more chances you have to get on someone’s radar, to show up for an opportunity, or for someone to hear your name or your idea. Charlie made a great point: someone is more likely to take a meeting with you, or invest in what you’re proposing, if they’ve heard of you before regardless of if you have a really cool powerpoint deck or not. Social media keeps you on the radar for investors, partners, and VC firms. Charlie pointed out that while he has met many founders the ones that stay on his radar by following and engaging with him on social media are the ones that usually stay within his orbit.
When celebrities enter the start up world does it guarantee success? Sometimes a celebrity CAN be a helpful to a company and move the needle but other times it doesn’t make a difference at all. It comes down to two points: how authentic is the alignment and how involved is the celebrity in the company. Are they actually involved or did they just attach their name to it and walk away?
Charlie hears a LOT of pitches, so naturally I wanted to hear what the secret is. What makes a good pitch? What makes a bad one? The answer was more simple than expected. A bad pitch is an unclear one! People try to impress with fluff and buzz words but sometimes the idea gets lost. Getting to the point and being clear is the secret to success. Be clear, tactful and confident.
Charlie also gets a lot of cold emails. Here are the strategies he says work best:
Know WHY you’re reaching out to the person and explain your why in the email.
Ask yourself if you can genuinely bring value to them, be honest with yourself on this.
Take time to look at the persons online platforms. If you mention something they’ve recently posted it’s almost a sure way to get a response back!
Charlie switched the script on me and asked me if I have specific goals with my personal branding and social presence…
Here are the 2 things I’ve focused on:
1- Connecting with others. My ah-ha moments usually come from things that other people have said to me in conversation. Therefore, how do I create more of these moments? Note: Charlie recommended the book, Where Good Ideas Come From by Steven Johnson which is all about the cross pollination of ideas!
2- The more you give the more you get! I create time to give more than I receive. Ironically, this ends up creating more opportunities for me!
Charlie aims to be the most accessible VC in New York but has very specific boundaries on how he does this. Scheduling is key. He tries to host 1-2 dinners per month that are set on a reoccurring basis. Creating replicable moments becomes easier as time goes on, therefore more opportunities become available to him.
Harry Stebbings was 18 when he started the 20 Min VC Podcast. He mass emailed a HUGE list of VC’s and one by one got them to agree to come on the show. The more people who agreed the more guests and access he got. He became so well connected that someone offered him his own VC fund! It’s a good reminder that even the smallest of steps can pay off.
The next big company according to Charlie? Esembly Diapers! It’s a reusable diaper that doesn’t leak and is environmentally friendly.
The next app you should know about? https://stoopinbox.com/ which is an inbox specifically for newsletters.
One of Charlie’s favorite scheduling programs or chrome plug ins? Calendly makes it super easy to schedule meetings without having to go back and forth on emails to find a time.
Best place for what’s going to be big? Charlie’s newsletter where I have gotten so many good resources and tips: NYCWeeklyNewsletter
Next week we’re having coffee with Myka Meier and talking all about business etiquette. Add it to your calendar. It’s going to be a good one!