Neil Patel

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Jeff Seibert is a repeat founder with multiple full-cycle startups and exits under his belt. Including going from zero to selling a company to Twitter for $100M in just 14 months. 

On the Dealmakers Show, Seibert shared how he gained a founders’ mindset, why it may make sense to skip a Seed round, his fundraising pitching strategy, what his latest company is up to, and your real job as the founder of a startup.

Listen to the full podcast episode and review the transcript here.

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The Ultimate Guide To Pitch Decks

Entrepreneurial Mindset & Startup Ideas

Jeff Seibert was born and raised in Baltimore, MD. At a very early age, he developed an obsession with computers (before it was cool) and was teaching himself to code by the time he was 13 years old. 

He discovered a list of startup founders and the colleges they went to on the internet. This was around 2000, and half of them were coming out of Stanford. That immediately made up his mind of where he wanted to go. Even if it took a little more convincing to get his parents on board. 

Being exposed to that experience and environment changed everything. It immediately immersed him in technology and an ecosystem in which the school and startups were closely linked. He was surrounded by aspiring entrepreneurs who wanted to create the next Google-like success story, while founders would often come in and give talks to the students. 

Beyond Stanford, Seibert had two formative internships. The first was at Apple. It was a big wake-up call. His childhood dream had been to work there. Yet, on arrival, he discovered it was a giant corporation that operated in a very traditional way. Because of the secrecy the company keeps, there was no collaboration between peers. You had to keep your office door closed, and couldn’t talk to coworkers about your work, even off-site. He craved an opportunity to be more in a more collaborative setting.

His next internship was at a small startup with an environment where everyone was in the same room, working fast, and collaborating together to get product out the door and scale their customer base. It was night and day compared to Apple. He was hooked. 

Starting Your First Business In College

Together with a group of friends in his senior year in college, Jeff set about evaluating startup ideas. 

He says they would meet together for a couple of hours a week. They would brainstorm ideas and write them down. 

They came up with many ideas, but whether it was not personally having the skill set for it, or something else, none seemed to be the one killer idea for them to create a business around. So, they decided to build an idea-sharing website. They used this as their project for their computer science class and ended up winning the competition. 

They kept on working on this project over the next summer and turned it into the company Increo. 

They met an associate from DFJ Venture Capital on campus, and that turned into a surprise $500k Seed round to go all-in on their venture. 

A year later, with some technology and 20k customers in hand, they found the fundraising climate had changed a lot. It was 2009, and every one of the 36 Bay Area firms they pitched for another round of funding said no. 

So, with just 30 days of cash left in the bank, they secured an exit to Box and sold the company.

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Selling Your Startup To Twitter And Google

Jeff Seibert’s next startup was Crashlytics. 

Box had employed the whole team from his last startup. They sent Jeff to help build technology in the R&D group out on the East Coast in Boston. He ran into many issues with apps crashing. He talked to others and found they were running into the same issues. Including Instagram co-founder Mike Krieger, who said he received more crash reports each minute than he could read. So, with Box’s blessing, he began working on automating crash reports in his spare time at night and over the weekends. 

Around the same time, he was also introduced to his co founder Wayne, who helped convince Jeff that his side project was actually a killer business idea. Wayne quickly brought big customers like The Weather Channel on board as beta users and Crashlytics was officially off and running. 

14 months after launching, Twitter had been reaching out, and they closed an acquisition worth a reported $100M, after raising just $6M through a Series A round. Ultimately, Twitter ended up selling Crashlytics to Google. Today, the product runs on around five billion mobile devices or just about every smartphone on the planet. 

If you are interested in learning about startup acquisitions and how you may be able to sell your own business you may want to read my latest book, Selling Your Startup.


After taking some time off to travel, Jeff and Wayne started brainstorming ideas for a new venture. They came at it from the perspective of, if they were to start a business, what would the biggest challenges or inefficiencies be. 

They struck on accounting. One of the big pain points for business owners. A rather unsexy, but vital part of any company. Specifically, they honed in on how reporting for accounting was so laggy and opaque. Especially, when you compare that to all of the real-time intelligence and insights you can get in great visual dashboards for everything else. Like marketing. 

So they created their latest venture, Digits, to solve this. 

They’ve already raised $32M from Benchmark and GV and are busy making their vision a reality. 

Storytelling is everything which is something that Jeff Seibert was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

Listen in to the full podcast episode to find out more, including:

  • Skipping your Seed round to raise a bigger Series A
  • Jeff’s book recommendation
  • Balancing your founding team for success
  • Fundraising strategy
  • Getting Tim Draper to fund your business idea without a pitch deck


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Neil Patel

I hope you enjoy reading this blog post.

If you want help with your fundraising or acquisition, just book a call

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