Getting to Know Our Angels & What They Say About Angel Investing

Wondering who these crazy people are that keep investing in local startups? Well we’ve been asking ourselves the same question. We’d like to share what we’ve been learning from our own Startup TNT investment community. They have tips to share with founders and first-time investors on investing (and life!).

I sat down with Hassan in February, and got to learn so many cool things about him. 

Hassan is a retired Air Force officer, who is currently working as a reservist for the Air Force, doing flight instruction on their advanced jet trainer. During our conversation, he dropped this incredibly cool fact so humbly… the same as I would say “I have peanut butter toast for breakfast.” It really illustrates what kind of guy Hassan is—kind and humble and super smart.

In his 30 years with the Air Force and military, Hassan was also involved in engineering, project management, design development, operations, flight tests for various programs, and was deployed both domestically and internationally. 

And on the business side, Hassan and his wife, who is a dentist, acquired their first dental clinic, developed their business plan, and then went on to acquire a few more. And as the military side of his career slowed down, and the pandemic waylaid his plans to go into commercial flying, Hassan realized that he wanted to be able to stay home in Regina more. And that’s when the angel investing bug got him, and now here we are! 

AA: Why did you choose to start angel investing? 

HN: Angel investing has been a change for me. I spent 30 years in the Air Force (laughs) so this is really different. 

From both sides of our family (my wife and mine), we’ve known of entrepreneurs and startups (in Silicon Valley, New York, Texas, etc.), and I was definitely interested in supporting local businesses here in Regina/Saskatchewan, and I wanted to get more involved in business, in general. 

For me, I knew that because I wanted to make a change from my 30 years in the military, and get more involved in business, I would have to meet more people and expand my network. That’s how I got involved in angel investing. 

AA: What do you think is important for first-time angel investors to know? 

HN: Before I was involved with TNT, I had actually invested in StoreToDoor (which ended up being Summit IV’s Saskatchewan winner) in their pre-seed round. I talked to Scott, and then I would think of something or do some reading and Googling, and then I’d email him questions, and rinse and repeat. I didn’t know then that I was actually doing due diligence, which is the most important part! 

I think first-time investors need to prepare themselves to do a ton of due diligence and learning. Way more than you think you’re going to do. If your impression is that you’re going to hear a pitch, do a little talking and then sign on the dotted line, then you’re going to be very surprised. You need to educate yourself, really learn about the business and the industry, and make sure you’re totally comfortable with what the founder is proposing. 

AA: What are some of the big investing mistakes someone can make? 

HN: I think, other than not doing your homework and due diligence, it would be being too emotional. You need to have some emotion, and use your instincts, but you need to make sure that you utilize your quantitative skills to make decisions too. One can’t outweigh the others. 

AA: What should founders/startups keep in mind when pitching their companies or ideas? 

HN: It’s very similar to what I said above—it’s about balance. Founders sometimes concentrate too much on having all the data. They forget that in a pitch, you need to be able to win the person’s heart too. The pitch needs to be balanced—it needs to play to both the analytics and the emotions. 

For example, myself and a few other TNTers have just invested in Teal EV. We initially heard of their business during Summit IV, but they didn’t make the finals. We kept talking to them, and we’re actually making an even bigger investment than normal—we’re investing time AND money. And this is based on our gut instincts. Even though the larger investment group didn’t choose them as a finalist, there was something there, something that called to each of us investors, to keep the conversation going. 

AA: Why do you think it's important to invest in local companies? 

HN: Well, for one, my wife and I are local business owners. We want to continue to invest in our local economy, and to invest in local startups, so that Regina and Saskatchewan in general, can grow and get attention on an international level. 

Plus we have children, and with a better local economy, we’ll hopefully have a better tax base, more hospitals will open, more schools will open, and so on and so forth. 

AA: Lastly, what makes TNT different from other investing groups you've been part of? 

HN: I’m actually only part of TNT! I have investigated others, but the equity of the vote, the due diligence process, and the education sessions are unique to TNT. The education sessions were the highlight of the fall Summit for me. 

AA: That’s so awesome to hear. Thanks so much for your time today, Hassan!