How Digits CEO Jeff Seibert grew Digits to $29.9M revenue with a 94 person team in 2024.

hey folks my guess it is jeff cyber he's a serial entrepreneur and one of insider's top 100 seed vcs he's created products that are required by google twitter and box and angel invested in more than 60 startups and start on the netflix phenomenon the social dilemmas newest company digits is revolutionizing business finance jeff you're ready to take us to the top i'm ready looking forward to it nathan all right what's more fun exiting to google or starring in a netflix show oh man both for very different reasons and i'd say neither were expected um i sat down for a nice two-hour interview back in 2018 and had no idea i would be front and center in the trailer in the movie etc so what a surprise that's amazing okay you're working on digits today but we need to capture some of your backstory so let me put this in a point in time just so everyone can relate how old are you today i am 36. when did you launch your first company i launched my first company back in 2008 um so i guess when i was 23 or so and that was a tiny startup called increa we ended up raising money from dfj we ended up getting acquired by box in 2009 as the first acquisition era and levy ever made um and so that was a quick run but learned so much in that journey and and be honest with me there financial windfall for you or not really more of a good learning experience it was a learning experience except for the fact that box went on to ipo a decade later and so did you get stock we did it was an entirely stock deal and so in retrospect it panned out that's hysterical okay so it's a 100 all stock deal maybe at the price at the time not exciting but then you look back and go if you held that felt really good exactly and i not only held i still hold a lot of the shares today so i've been riding it the whole time did you do you have any interesting and interesting takeaways there you know a lot of people will look at the vc path and you've now gone through many cycles and invested on the other side if you're only optimizing to build like a happy healthy life and you want to be in sas and you want you know 10 20 million bucks many people would arg i mean i look fair enough i would argue you have a better shot at bootstrapping and building a 15 20 million dollar business than you do doing what aaron did which is dilute yourself down to sub five percent ipo time over a decade long period and deal with all those stresses from your vantage point do you agree or disagree with any of that today i agree with you back when aaron started box it was a completely different world it was very hard to convince these companies to adopt quote cloud quote sas right they were at the forefront at a lot of this and so i think he took the path he had to to build the business but today you're right i think it's a different world and if you have the opportunity to bootstrap a business i think you're in great shape very interesting okay so that was your first a deal and so sorry right how old were you when that happened that then i was 23. 23. okay so what would you skip right out of college or skip college or what yeah right out of college basically senior year my co-founder and i just failed to apply to jobs and so we started working on our own stuff got very lucky to raise a small seed round half million dollar seed round terrible terms honestly looking at it from today's point of view um but it was enough to get started and we hired a couple engineers and built a product that's amazing okay so and creo then exits the box do you stick around box learn a little bit or no you get bored and leave yeah no i stayed two years they made me an engineering manager and sent me to boston to launch their r d office on the east coast and that was a fascinating experience sort of first time in a management role at a bigger company i had great time building out a team out in boston and that's where actually the idea for crashlytics came from and so ended up giving notice a box and starting uh my next thing so crashlytics was launched in 2011 i think you would have been what 26 at this point 27 now yep 26 i think yep 26. okay and what was the original idea behind crashlytics yeah so it turns out mobile apps crashed so if you think in 2011 uh you're we're two years after the the sort of launch of ios apps right those came in 2009 oh what's going on there youtube good to see you guys now imagine this you love watching these interviews with sas founders but imagine if we took all of the valuation data out from over 2807 interviews i've done manually saves you a lot of time well we've done this we've built it into the beautiful interface inside of founder path check this out i'll show you how you can access this in a second but you log in you connect your stripe account you see your valuation real time you can see what it changed over the past 88 days and even set goals for valuation this year now the secret evaluation is there's many different ways to value a sas business so the reason you're going to see three or four different valuations inside of your frowner path dashboard this is all free by the way is because depending on who's doing the buying of your sas company you're going to get a different valuation a vc is going to pay a different valuation private equity firm is different if you're going to do a minority sale that's different and if you sell the whole business that's a different valuation you can see all those when i hover over here right so the teal is what a vc would pay yellow is what private equity and red is if you sold the whole thing outright now what's cool about this is this is not built off random data again you guys hear these interviews on youtube all these datas are built from real-time valuation data points founders share with us on the show so traction 1.2 million seed round 3.7 raised they sold 22 to their business go in here and filter by the event maybe you only want to see companies that have sold the whole business well here are a bunch that have been acquired the valuation and the multiple maybe you're going out right now and you're raising your seed round well go in here and look at all this recent seed deals that went down what they raised what valuation they raised at and what percent that they sold there's never been a larger data set of sas valuations and what you can get now inside of founderpath and we're thrilled to bring it to you all right we're going to go back to the youtube video here in a second but if you want to check this tool out if you want to jump in and sign up you can check it out for free to get your valuation at this link this link founderpath.com forward slash products forward slash evaluations or if you go to founderpath.com and hover over products click on get your valuation here and go ahead and sign up to give it a whirl again all that valuation data live right inside the platform i hope to see you there all right let's jump back into the interview everyone's building apps the app store is flooded with reviews 10 of them mentioned the word crash it was a very unstable very early platform and i became obsessed with crash reporting through my work at box because we were facing our own internal issues with our mobile work and our mac os work and ended up building a prototype on the side and i asked box hey can i work on this nights and weekends would that be cool and to their complete credit they were like yep great go for it it's totally unrelated to box and if it's good maybe we'll use it and so started building they let you own the ip that wasn't tied up in your ip and employee agreement with twitter box exactly and that's what i asked him for and they let me own it free and clear that's amazing so yeah huge props to box and aaron for doing that um and ended up of course the side project gain steam got more interesting um and so ended up giving box of many months of notice had a smooth transition out and then started working on crosstalk full-time um it looks like you had what 10 11 people participate in the seed round in 2011 at crashlytics did aaron write a check into that did some of your former you know bosses write in checks into that not at the time um aaron did join as an advisor after the seed round uh which was great but yeah we ended up because we're in boston we wanted to really raise from the local ecosystem and so we got a group of 10 boston angels to seed it which was fantastic as well as a local from there called flybridge capital uh what was the market like in 2011 for that for a seat it was like was a five cap out of the question it was it was yeah we raised one on five that's exactly it oh okay good that's great um and so yeah that worked well of course again in today's language like crazy different world um but we were very happy with it and we ended up building the team um and then it was a very quick story basically 14 months from launch to being acquired by twitter yeah no flybridge participated in the one on 5 in 2011 that's also convenient they look at your monthly updates they go jeff please let us leave your lead your at least be involved with your a you raised five on in the a round what evaluation was that at...