Welcome to The Leap! For this IG Live series, Wethos CEO Rachel Renock sits down with entrepreneurs who took the leap toward working independently or starting their own project.

In this episode, Rachel sat down with David Greenberg, founder of Greenberg Growth and Greenpepper Studios.

David has a background in eCommerce and growth marketing — mainly around web optimization, Facebook, Google, and email. He's worked in-house at several large tech companies,  including Bread Finance and Maisonette. David began his entrepreneurial career in January 2021 leading a growth marketing agency studio called Greenberg Growth and he recently launched a new business, Greenpepper Studios, which focuses on TikTok and helping large brands match with creators.

Watch the full interview here, listen on Spotify, or read below to learn more about how David leveraged his network to get his business started, what metrics he uses to measure success, and his advice for anyone who wants to take the leap into entrepreneurship. 

Note: The following interview has been edited for clarity and length.

RR: Can you tell me a bit more about your journey and how that's evolved over time in terms of starting your business?

DG: Before I even started my entrepreneurial career I felt like I took a big risk. I was a financial analyst at a big Fortune 500 company but knew it wasn't what I wanted to do for the rest of my life by any means. So me and my now-fiancee, Lauren, moved up to New York City. I had no clue what I wanted to do but I knew I wanted to do things that were going to affect the bottom line of the company. I met a really awesome guy who took a chance on me, took me under his wing, and taught me everything about Google Analytics, growth marketing, Facebook Ads, Google Ads, prospecting funnels, retargeting…marketing 101 basically.

That’s how I found my niche within eCommerce and conversion rate optimization and analytics, and that was at Maisonette. Moving on to Bread Finance — a buy now, pay later company — they had about five hundred to a thousand companies under their belt. So I got to see all these different companies, what was working for them, what wasn't working for them.

When Bread got acquired by a bigger company, kind of the employees got taken care of. Got some equity that cashed out into our pockets.

And it wasn't much by any means, but it was a couple of months’ rent that gave me the confidence to say, "Okay. Let's give it four, five, six months and see what we can do."

That was how Greenberg Growth started. I got my first opportunity through my girlfriend's agency [because] they had talked to me before I had made the leap. That's one piece of advice I would give to anybody thinking about doing it — work your connections and see if there's somebody who will be ready for you when you're ready to make the jump. Try not to start with zero clients. Try to start with maybe half a client or one client. That was the confidence I needed to say, "Okay. Let's give this a roll." And sure enough that just led to more opportunities.

RR: I'm curious to get your perspective on going from having a full-time role in-house somewhere to starting your own freelance consulting business. What were some of the biggest challenges initially in that first year? Were there any advantages you had because you came from that background?

DG: I mean, advantages definitely being the network — the tech community people I worked with at Bread, people I worked with at Maisonette, were definitely the number one source for clients. People that know you, are cool working with you, and definitely enjoy working with you, I think that's a big [advantage]. People want to work with people they like working with. 

As far as the challenges, I could pull out a list of a thousand things that have been challenges. They're a little bit easier today than they were a year and a half ago, but they’re nonstop and they're constant. Being able to be in control of those challenges and have your own autonomy over the big things that come up, it's life-changing in both an awesome way and a, "Hey you'd better be ready to carry this around all the time because it's all on you” way.

The top challenges I'd say are invoicing, dealing with payments — which, hey thanks Wethos, you guys have made my life much easier with that! — taxes, and accounting. So kind of within the same vein. That was definitely the biggest hurdle. But yeah, there's platforms like Wethos and other ones coming out every day within the Web3 community and also the historical fintech community that are trying to make that a more seamless experience.

Because yeah, when you're doing your first invoice, it's definitely a bit scary like, "Okay, how does this money actually get to my bank account?"

RR: You mentioned that a lot of your clients come from your network, which is a trend that we see a lot. What does your sales [process] look like there when it comes to your network? Thinking tactically, are you super direct and tell people, "Hey I'm available!" or do you tweet it out and let them come to you?

DG: I've made the mistake of not blasting it out to the world when I first started. And that's something that I started doing as recently as today. I haven't been super gung ho about posting stories, posting on LinkedIn, posting on Twitter even though I'm on those networks pretty constantly.

But it was definitely letting the right people know. The people who I knew who would kind of be within that world, like agency owners and other agencies that I had worked with in the past and being like, "Hey I'm doing this now if anybody's looking for people, let me know."

The one thing I would just nail it down to is to be helpful. Be the helping hand for somebody. Say, "Congrats!" when they get a new job or a promotion. Be within their world. Keep poking, or as I like to say, “stoke the fires.” You obviously hear in sales and in life that relationships are everything. And yeah, those relationships I built at my full-time jobs are the reason I can freelance and do what I do today.

But yeah, still working on putting myself out there. Pretty much every client for Greenberg Growth, my initial growth marketing business, was all referral-based. Whereas now with Greenpepper Studios it’s like, "Okay. We're going out and selling this and putting this out in the world." which frankly, is a lot scarier. But at the end of the day, if you look out for people, they'll look out for you.

RR: I want to switch gears and talk a little bit about metrics for your own business. Something that a lot of people struggle with is how do you define success and measure success as a freelance studio? What do you think about that? I imagine as a growth marketer you must be metrics-oriented but is that the case for your own business?

DG: With Greenberg Growth, especially during Year 0, it was very much, "Can I do this and pay my bills?" which isn't a super-defined KPI, but yeah for me it was sink or swim. Like, "Can I survive doing this?" I definitely knew what numbers I wanted to reach but it was more like, is this sustainable or not?

RR: What are some of the metrics you measure besides revenue? Is it leads? Is it our close rate?

DG: Since a lot of my business is all through my network, I gave myself a challenge of 99 cold outreaches for Q3. Frankly, I'm not on track right now, but you don't need to have all your ducks in a row to be able to launch and do cold outreach.

Another metric I have is based on making a certain number of TikTok videos — we are on track with that one.

I will say that there are about six of them, and three out of the six were very monetary and client-based. But at the end of the day, they’re about getting yourself ready and in a spot to succeed where you want to be for the next quarter.

And you don't have to do quarterly goals. You can do it for the year. You can do it for two years. You can kind of break it up on whatever time horizon you want. But that felt like a good spot for me to think about what I want long-term.

RR: Any advice for folks that are going to take the leap?

DG: You can make your own time horizons. You can set your own tests. You only lose when you quit. You never know when that next opportunity is right around the corner. There are macroeconomic factors at play. There are your local community factors at play — there's opportunity everywhere. So don't give up and keep working and you never know when that big client or that big opportunity is right around the corner.