How Gatsby CEO Brett Bernstein grew Gatsby to $120K revenue and 100 customers in 2019.

hello everyone my guest today is brett bernstein uh he's a two-time founder sold his first company at age 24 and then worked a box through their ipo and started his latest company gatsby in 2017. he's been through a ton of entrepreneurial ups and downs from founder fears to selling a business that helps 50 000 students eat healthier every year again now focusing on gatsby which helps identify and engage your most influential customers brett you ready to take us to the top sure nathan thank you you bet so that first company you sold at age 24 was that the the student kind of eat healthier business that's right that was natural cravings uh it was a great passion project that we grew out of uh the obamas coming into the white house and we were there to fill that that void that michelle obama came up and said hey students have this obesity epidemic here especially in california and we were able to help aid her mission by providing healthier food options for school districts throughout the state bro what do you mean michelle obama just came up she doesn't just come up to people how'd that actually happen oh sure so uh if you remember one of michelle obama's most um probably recognizable initiatives when she was in office as well as first lady was around you know creating awareness around the obesity problem in america and her focus was on children and so we happened to have started a business my my father my friend and i a little before she came into the white house and we were focused on healthy school vending and then when she came in and put you know shown light on the issue we were able to really capitalize on that on that and what was the model there i mean obviously that wasn't software were you just selling and making margin off kind of food you were putting in cafeterias yeah we actually supplied the complete top to bottom solution we provided the healthy vending machines themselves we did the restocking and we also did the best part was picking the products themselves right so again to decide what was uh the best for the schools and students we had technology in there as well that would tell us what was selling the best what was out of sell and was to be restocked and it was very efficient and processed why did you sell the company so we grew too fast which is a great reason but uh unlike software it's not as scalable to grow physical businesses so we had to deal with increased employees insurance vandalism things like that that were like basically we got three major school districts in the course of one week and we had to have hundreds of schools um with machines by end of summer which was about three months away and so we looked at our options we tried to partner with a food service business that was already distributing hot foods to those school districts and ultimately we decided that the best thing for our students in the schools was to sell to a larger company to actually be able to deliver in time and was this like a life-changing moment for you to the point where you don't have to worry about money the rest of your life or was it more like hey this is a great learning experience i launched company i sold it now i'm going to go into box uh yeah it was definitely life-changing the standpoint of the experience right um it was incredible to grow a company from nothing up to an acquisition uh be part of a mission that was extremely close to my heart and uh it propelled me into my next career okay so how did you land in a box after that so when i sold right so actually i had some friends from college who were working at boston in the very early days uh so i was familiar with them and when i sold national cravings i was actually in the bay area where boxes based so as i'm negotiating the sale of my first business i'm actually uh interviewing with box and that experience got me into a great position there and helped me grow pretty fast with the company because your friends kind of obviously brought you in there and then app box helped me understand so it sounds like you started there in maybe 2012 where did you kind of accelerate to to the year you left so i loved my time at box it was so exciting to work there with aaron levy and the rest of the great team there um i got fortunate enough to come on to the customer success team actually what i was choosing uh to work on at a time when it was a very small part of the company right there was maybe 10 or so people managing tens of thousands of clients right and so i got lucky enough to get in there early enough to work with some of our most recognizable brands at the time i will mention their names but i almost did and that allowed me to have a lot of exposure and and understanding of how enterprise software works so over the next two and a half three years i actually worked my way up through through box ended up moving to the marketing side um helping directly with our strategy around partnerships integrations with the ecosystem so we're talking about microsoft dropbox google how we compare and contrast and work with those folks and then eventually decided after the ipo that i took you know i'm now in my late 20s at that time and i decided let's take my experience with my first business which i grew from zero to acquisition and then my experience with enterprise software box which i was at from a couple hundred employees through over a thousand and take these two things together and find my next business for myself and that's where gather was born okay so what year was that uh the idea for gatsby started in 2015 the tail end of it so almost 2016. first line of code was 2016 as well that's right okay so uh first line of code then and then help us understand again what what the company uh does okay so here's actually a very interesting story um i didn't sit down and decide i want to build a marketing or social media company i never believe that that's really how the best ideas are created uh rather it's through iterations and customer feedback so when a very first iteration of gatsby was very very different than it is today we had i looked around at the market and said what do i know what am i skilled at and where are their problems and my number one philosophy when starting a new business is look for a business model that currently exists but only services an elite minority of the population if you can modify that business model and make it available to a larger audience that's an investable and scalable business that was my approach so i was looking around i came across a concept at the time called social media vending um large brands i remember very specifically old navy would do this strategy they would launch a new a new location a new storefront outside of the location they would have a vending machine it'd be branded as old navy it'd be stocked with slippers the side of the machine would say tweet for your feet and as you walked by the vending machine patrons would be encouraged to tweet about old navy in exchange for a free vend of slippers yup makes sense very cool concept of converting foot traffic into marketers leads but also marketers right that was the idea so i started so my very first few weeks of gatsby was wow really cool idea but very expensive talking 100 000 a month to run a campaign like this not accessible to most brands so my thought was if i can walk around to malls and movie theaters and have them place a turnkey machine that's branded my own branding but it has the same idea where they can just rent access for a week or a month at a time and have the same ability to convert foot traffic into their patrons that's a good business within two weeks i actually had a major mall in la give me an agreement to sign in time for black friday and right as i said in the agreement i'm like having flashbacks to my time running natural cravings where i thought oh my gosh too fast yeah hey just bro there's a lot of story you want to capture so speed up to essentially how you pivoted from the physical stuff to where you are today with the instagram handles and virtual influence so at that very moment before i signed the agreement i decided i spent three and a half years at box how can i pivot this into e-commerce right where on where in the e-commerce landscape is a vending machine quote-unquote and i discovered the pop-up window so the pop-up window exists on almost every single website and it's the same idea give us your email in exchange for a reward that's a vending machine in many ways so i thought if i could make that experience social what would that be like would brands like it would consumers do it so our very first version of gatsby uh very easily was like follow us on instagram in exchange for a discount code yeah and in the process of that happening we captured email address and more data points as well including follower stats there were some issues with that first version you know let's just say we had to go through the api and there was drop off and obstacles right but the overall premise worked we put our heads together came up with a better version which exists today and luckily timing just like the time with the obamas and my first business we had luxury of fire festival help us out tremendously here as well so about two years ago right we're about to launch our product the new version the fire festival takes place are you playing with the fire festival yeah yeah i think i think our audiences as well so and just fa bret fast forward okay we're taking a lot of time here on the...