Alex Robinson is a serial entrepreneur who has raised significant amounts of capital to take on big opportunities. His latest venture has already pulled in nine figures and has a lot of room to grow.

During our interview on the DealMakers podcast, Robinson talked about his experience working at Microsoft, facing big external risks in business, finding the right cofounders, what really matters in building a successful business and digitizing the giant commercial real estate space.

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

Figuring Out What You Don’t Want To Do

Much of our early lives and careers are spent figuring out what it is that we don’t want to do. As well as perhaps picking up a few nuggets, skills, and passions that entrepreneurs end up putting together for great successes later on.

Alex Robinson grew up on the Kitsap Peninsula. A small town reached by a long ferry boat ride from Downtown Seattle. 

Virtually his whole family was in medicine in some way. His grandfather was a surgeon. His sister and father are dentists. 

Alex knew he did want to be in medicine. However, as with many physicians, his father was also into real estate. Since he was 12 years old he remembers his father getting him up at seven in the morning on Saturdays to go help manage his properties.

Like most of the successful entrepreneurs that have been featured on the Dealmakers Show Alex also found a passion for travel. Even before having Google Earth, he remembers real atlases and globes. In both his junior year of high school and college he enjoyed living in Spain and experiencing new cultures. 

He also found he liked building things and was interested in business. In college, he took business administration.

Lessons From Working At Microsoft

Returning from Spain, Alex found the only internship position left was at Microsoft in Redmond, WA. He fell in love with the technology and tech business. After college, he ended up going to work there full time for the next six years. 

This was a fast growth period for Microsoft, right when Bill Gates was handing over the reins. Robinson says he was around employee 21,000. There were around 100,000 when he left. 

He started in finance and then moved into corporate strategy and product. He ultimately ended up working on OneNote and what is now Office 365. 

Alex shared with us some of his great takeaways from this period, which he has also rolled into his own ventures. 

1) Precision Questioning

Precision Questioning was a technique used by Steve Ballmer and Bill Gates. It’s all about asking questions to dig through the layers and find the limit of their understanding our weaknesses. Alex says he’s also found it to be useful in interviewing and learning.

2) Pricing & Packaging

With Office, he learned about the advantages of packaging different tools into a package which can be greater than the sum of its parts and be more sustainable and consistent.

3) Company Culture

While he admits it may have been effective, Alex didn’t always enjoy the adversarial environment at Microsoft. It’s something he’s tried to do differently with the company culture at his own companies.

Climate Change & Big Business Risks

After several years at Microsoft, Alex decided to return to business school at Stanford. He saw this as his chance to really be intentional in what was next, rather than just falling into one thing after another. 

Specifically, he was interested in the intersection of climate change and alternative energy, business, and entrepreneurship. He also found he really had gained a love for software after working at Microsoft. He began looking for a way to apply this to combating climate change.

In just his second year at Stanford, he found his first business opportunity. His first company GreenDoor took on climate change from a financial angle, providing tools for counties and local lenders. GreenDoor was largely reliant on the green energy subsidy program at the time. He was aware of the risk but admits he hadn’t really thought ahead as he could have. The business was going well. 

Then one morning he woke up, the subsidy was gone, and effectively the entire business was too. A big lesson in creating a business at risk of external factors and regulation out of your control. 

Despite this GreenDoor was acquired, and this led to a founding VP role in a new venture, New Energy Risk, an energy insurance company. This company was again acquired by XL Kaplan. 

Juniper Square

For his next venture, Alex decided to take on a new industry, and then to find a way to still fulfill his passion for the environment from the results.

He re-discovered real estate. A market he found to be almost as big as America’s public stock market. One worth an estimated $15-20T. Yet, also one of the most antiquated and inefficient markets. One begging to be digitized. 

The company essentially operates an online-based platform for private equity firms to find, raise, and manage capital. It provides an easy-to-use software that streamlines fundraising, investment administration, and investor reporting. With Juniper Square, clients improve investor satisfaction, boost fundraising productivity, and save time and money on investment operations.

So far, his answer to transforming this industry, Juniper Square has already raised $100M through a Series C round. They have accumulated close to 1,000 GPs, including big funds and fund managers, pension funds, and others who are also customers. 

Storytelling is everything which is something that Alex 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.

Cofounders & What’s Most Important

This time around Alex says he really knew that he wanted to go at it with cofounders along for the ride. He tried the cringeworthy cofounder meetups, before being introduced to Adam Ginsburg and Yonas Fisseha of the Epinions Mafia.

This time around he also says he stopped playing startup. They went for a long time without having a company website or even a company name. They simply didn’t need it to actually start making things happen and secure customers. 

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

  • Navigating big external risks
  • Choosing cofounders
  • Saying no to nine-figure M&A offers
  • Strategizing the takeover of big industries
  • The only one thing that really matters when building a company

 

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