Jaron Waldman knows a thing or two about building startups. He has launched and scaled at least two ventures which have been acquired by some of the biggest giants that have ever existed.
Jaron and I recorded an episode of the DealMakers podcast together. He told our audience about his experiences launching and growing companies. He shared insights on going full circle, learnings from working inside these enviable acquirers, the pitfalls to watch out for, and the pros and cons of both bootstrapping and raising VC money.
Starting With Computers At 11
Before making his way to Silicon Valley, Waldman was born in Toronto, Canada.
Both of his parents were teachers, and his family provided an environment rich in education. That included an uncle who got him into Unix systems at a young age. He got his first PC at 11 years old. Even with a dial-up connection, he found a passion for building things and hacking.
He began building websites and setting up servers before setting up databases for some big Canadian banks.
Fascinated by what was happening in California Jaron put his education on pause, and went to work for a startup whose founders have sold a business to VerticalNet.
Then as the dot com bubble burst, he decided to pick back up on his studies at UCLA. There he found the seeds of his future business in location database work that mapped changes in neighborhoods.
First Lessons In Fundraising
Jaron began on his own by starting with a nonprofit. He quickly learned a big lesson about funding.
They began with the noble idea of being able to impact policy and helping others to recognize the impact on policy on neighborhoods and communities and their residents. They got funded by one of the biggest institutions in the space, Fannie Mae.
Unfortunately, while Fannie Mae put up 90% or more of the money they needed, the organization then decided they’d rather pay for a product to serve their needs instead. They lost the funding but did gain a customer. It was an important lesson in not having a diversified investor base.
Fortunately, Jaron was able to spin this into a bootstrapped for-profit business.
Bootstrapping Vs. Fundraising
Placebase became a consulting and product business that came out before Google Maps.
While it was very tempting to keep on taking all the consulting and customization work being offered, Waldman says it was critical to reinvest in the core product and say no to that business. They were disciplined, focused and worked hard without taking in any outside money.
They ended up counting AOL (Mapquest) and Apple as clients. They were acquired by Apple.
In contrast, Jaron’s more recent company Curbside raised almost $60 million from top investors. He says he enjoyed both paths. Bootstrapping makes you focus, hit product-market fit fast and make a profit. Otherwise, you aren’t going to make payroll next week.
Raising millions can feel great. It can give you more freedom, more credibility, and the rocket fuel to go fast. Of course, he says that can cause you to blast past your target and it can blow up in your face a lot worse. It makes it much harder to focus on what is most important.
Storytelling is everything which is something that Jaron 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
ACCESS THE PITCH DECK TEMPLATE
Quick Insights From Working At Apple
During his tenure at Apple some of his big takeaways were:
See How I Can Help You With Your Fundraising Efforts
- Fundraising Process : get guidance from A to Z.
- Materials : our team creates epic pitch decks and financial models
- Investor Access : connect with the right investors for your business and close them