His First Business Failed, Then He Sold His Second To Apple, And Just Sold His Third One To Rakuten For Millions

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.

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

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

Quick Insights From Working At Apple

During his tenure at Apple some of his big takeaways were:  

• How far they planned ahead
• The process of green-lighting projects and products
• How teams pushed each other to innovate and deliver a better product
• How quickly you can move away from the frontlines of a hands-on building of things
• How it can take removing yourself from the busyness to get clarity 

Fundraising  

Jaron’s next venture Curbside raised a seed round pretty quickly, based pretty much on his cofounder and a napkin business plan. They would provide a SaaS solution to power retailers.

Across four funding rounds, they raised almost $60M in capital. That was led by Yahoo founder Jerry Yang. They even used his office to incubate it.

They landed Target as a flagship customer early on. They were in 150 of their stores before a new CIO decided to cut them off and try to bring it in-house.

That didn’t stop them from growing and bringing in strategic investors like CVS. Of course, this can always be an interesting situation, when you have VCs looking for an exit and strategics thinking about long term integration.

It’s a similar dilemma when you get a great buyout offer, and the acquirer courting you is saying all the right things. You just never know if they’ll really follow through with giving you the resources you need, and the ongoing autonomy to do the best things for the mission and customers. At least for Curbside, it worked out well in their exit to Rakuten.

Advice For New Startup Founders

Asked for his top piece of advice to his younger self, Jaron Waldman ways it would be patience. As a passionate entrepreneur, it can be compelling to rush in and hustle away. You want everything to happen immediately. That has benefits. Without that attitude, you might never start.

Yet, that also has to be balanced with patience and big picture thinking. Know that everything is going to take longer than you expect. It is probably going to be harder and cost a lot more too.

You can get there, but be ready for a variety of twists and turns on the journey. If you can think further out, it will help keep your perspective and perhaps better ensure your success.

As an example, Jaron says it can take a lot longer for markets to develop and mature than you think. There have been plenty of failures when entrepreneurs are too far ahead of their time.

Especially, when they don’t have the staying power to wait for the world to catch up. Then you are just leaving the space open for someone else to pick up the pieces and run with it.

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

• Learnings from failure
• How to deal with fundraising hurdles
• Validating new business models
• How to navigate acquisitions

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