Work-Bench Spotlight: Daniel Chesley On Finding an Edge as a New Investor

Jan 8, 2024
Work-Bench Spotlight: Daniel Chesley On Finding an Edge as a New Investor
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Danny is an Investor at Work-Bench where he focuses on AI/ML, developer tools, and enterprise applications. He authors the More Intelligent Newsletter, where he shares the latest thematic research and technology trends he’s digging into.

We sat down with Danny to learn about his coming to VC journey, uncovering the highlights, standout moments, and unexpected twists along the way. Check it out:

Why did you decide to become a VC? And why Work-Bench?

I started my career at IBM, but as a curious person, I wasn’t particularly excited to pursue life at a big company. My family is entrepreneurial, and I knew the minutiae of day to day corporate life wasn’t for me. I wanted to make my own mark. I eventually dove into the world of startups joining Hyperscience. 

Over time, what drew me to VC was the opportunity to work with multiple companies at once. Working at one company allows you to think very deeply about one specific problem. But working across a portfolio of investments allows you the flexibility to dive into different spaces, and follow your own curiosity. 

From a firm strategy perspective, venture is a crowded space and firms need to play a differentiated game to be successful. When I first met the Work-Bench team, I was immediately attracted to how unique they were from other Seed and even multi-stage firms: 

  1. Team: First off, they’re all really great people. Thinking about building my career in venture, I wanted to surround myself with not only smart people, but people I enjoyed working with every day who I could learn from. 
  2. Grit: When Work-Bench first started 10+ years ago, they were able to hustle and prove value. Over time, this helped them win allocation into what would become unicorns like Cockroach Labs, Socure, Dialpad, etc. They also built the NY enterprise tech community from scratch, and I saw all of this as a testament to their grit and differentiated investing model. 
  3. Apprenticeship: From a firm perspective, Work-Bench is probably the most collaborative and value-driven firms out there. What I’ve seen is that many venture firms offer “two year and out” programs. Whereas I saw Work-Bench as a long-term opportunity where I’d get to work alongside people who themselves have grown and taken it upon themselves to level up their teammates.

What are 3 lessons you learned making the transition from operator to VC?

  1. It’s a long term game. Unlike public markets or private equity where the timelines are shorter, in early-stage venture everything you do has delayed gratification. If you meet a founder today, it may not result in an investment for over a year. Or if you meet an operator today, they may not be thinking about leaving their job and starting a company of their own just yet. It’s about building long-term relationships, so that you’re the first call people make when they need advice, start building something new, or begin fundraising. 
  2. Trust the process. Venture is a long feedback loop. You won't know if your research and relationships will lead to anything for a long time. So, it’s important that you enjoy playing the game. 
  3. Venture is a privileged job. Those in the ecosystem regularly seek out and can rely heavily on your opinion - many founders and operators could make company-altering decisions based on it.. In this sense, being in venture is a privileged position. Take that responsibility seriously and be aware of the messaging you give off – be well researched, well networked, and well thought out, while giving unbiased feedback. In short, don’t spew bull sh*t. 

What’s a piece of advice you would give to someone looking to break into VC?

First, identify what you’re optimizing for in your career. If you’re solely looking for a high status and glamorous role, this likely won’t be the job for you. Like I said before, VC is a long and competitive game where you don’t simply clock in and clock out…you really have to live the job and be genuinely excited about what you're investing in.

It's also important to develop your own taste and unique experience that makes you a compelling partner to founders. While this can come in many flavors, I'd recommend working at a relevant startup in your area of interest, go deep into the categories you care about, and identify investible startups even before you even land a role and can write a check.

What’s your best learning as a former operator?

Try to play to your own strengths. During my time at Hyperscience, I worked on both the product and GTM sides of the house. Now as a VC, I mesh those two knowledge bases together to help early-stage founders scale their businesses.  

What’s one non-obvious learning you’ve had?

Before becoming a VC, I used to think the best companies were those that raised the most funding and had the highest valuations (because markets are efficient, right?). But I quickly learned that a lot of the job is separating hype vs. reality, and that the biggest inputs to a successful fund are ownership and fund size. Not all that glitters is gold. 

‍‍If you’re an early-stage enterprise founder or operator — connect with us directly to chat about anything GTM or check out our events page to stay in the loop on all things happening in the Work-Bench community. ‍

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