Confessions of a Female Angel

By Francine Hardaway, Ph.D.

I am well aware that there aren't many female angels. It's the same reason there's a much lower failure rate in women-owned businesses.

The reason? Women aren't as risk tolerant and they hit singles rather than swing for the fences. I'd call my own first business either a single or a bunt :-) It did, however, afford me a lavish lifestyle and educate my two kids. I think we really need female angels, because it would make the businesses in which they would invest more successful.

Of course the role of women investors is changing as the workforce changes. In the beginning, I was so happy to be in the workplace at all that I accepted a salary that was a fraction of what I deserved, and then when I started a business I didn't grow if at all for years, and then only when I took on a male business partner (and married him). Now, women are beginning to dominate the workplace, and perhaps they will get some guts.

My dad, who was an investor, a broker, a lawyer, a gambler, taught me to invest. As soon as I got out of school and had a penny in my pocket, I began to invest -- first in the stock market, and then in actual companies. When I couldn't make payroll in my first business, I played the stock market for money. I still remember making a "killing" in Pulte Homes.

My first angel investment was $5,000 in a company started by a former student of mine, and when it went public I received $50,000. That was a fortunate lesson. If I had lost my money, that would have probably been the last angel investment, but the magnitude of the return (in the 1970's) got my attention.

Another crazy investment I made in the 70's was in the New Times, a rag started by two friends of mine that is now Village Voice Media. That was the original Friends, Family and Fools investment; we had a party in someone's house and a group of people who liked Mike and Jim kicked in to support them, never expecting to see a dime back. About ten years later, the boys bought all the original investors out, with appropriate vigorish.

Then I invested again in that same entrepreneur that gave me the 10x learning experience; this time, I (sort of) doubled down, in that I invested $5000 cash and the services of my PR firm. In that investment, the funders of the A round turned out to be the rock band U-2, and the angels (there were six of us) could either stay in or get out. I took my original cash back and stayed in for the rest. That company eventually sued Microsoft for something like $33 million and won; I didn't own many shares by the time the suit was settled, but I can't complain because I rode the stock up and down and even day-traded it a while. I was still more of a stock market fan, but the institutions were beginning to make it harder to win against them as a small investor.

When I came out of Intel after selling my own business, I began to angel invest in earnest. My current company, Stealthmode Partners, used to take equity as part of its fees in those days, and I have more stock certificates than you can ever imagine, the companies long gone.

Another of my investments (founded in 2000) broke even this year for the first time and will begin distribution to shareholders.

In the meantime, I have won and lost millions investing in real estate, a much less interesting business, but with entrepreneurs who need money just like any other. I invested $25,000 in some land outside of Austin, Texas during the dot-com bust and engineered the sale of it to a larger partner, making nearly 10x my investment and staying in for the upside ( if there ever is one after the carrying costs through this downturn).

I also made a ton of money flipping houses from 2004-2006.

And, oh by the way, I lost a million in real estate in 1990. And one partnership I bought into in 1986 still owns some of its original land, although we've been paid back many times over.

Last year, I lost $45,000 trying to start a bank.

Those are just the deals I remember; I've been in about 50 real estate deals and about fifteen tech deals. I am actually a deal junkie. Most of the men I talk to don't have my stomach for roller coaster rides.

But guess what? I'm a woman. They are SMALL deals. I've never lost everything, and I have had a fabulous time. I will obviously do this until I completely lose my senses.

Today’s article is presented by the founder of Stealthmode Partners in Phoenix, Arizona. She is a true angel investor, and has helped package and secure funding for many high-tech startup companies in the area. She has also created positioning and marketing strategies for dozens of growth companies. You can contact her directly at francine@stealthmode.com.

Morris Callaman – Entrepreneur Extraordinaire

A couple of weeks ago, I met a serial entrepreneur who is living proof that anyone can overcome major obstacles in his life, and still do amazing things. Morris came from a life of childhood abuse, and living on the streets, to a continuing successful career starting with big companies, then founding new companies, now investing in startups, and counseling startup founders.

In his 20 year career so far, Morris has learned to lead change, adapt to thrive, and fail quickly whenever necessary. He has an engineering degree, an MBA, and is a practicing attorney. Here are some interview highlights:

Marty: Welcome to Startup Professionals interviews. Tell us what you do now.

Morris: I am now an Attorney @Callaman Law and an Angel Investor @Callaman Ventures; I help other Founders grow their own companies.

In my investment practice, I invest in early stage, generally internet centric, companies where the founders have a strong sense of social justice. For example, I was one of the early investors in LifeLock and supported the Founders for the next year thereafter.

In my legal practice, I am Special Counsel to Founders: not general counsel, not corporate counsel. I protect entrepreneurs by adding to their team when they are dealing with professional investors, such as venture capitalists or investment banks, or when they are dealing with other lawyers, or often even when they are dealing with their own companies.

Marty: When and why did you decide to be an entrepreneur?

Morris: Like much of my life, I arrived at that particular insight little by little. I am on my fourth successful startup now. We all have our strengths and weaknesses, so being an entrepreneur certainly isn't for everyone and my earliest entrepreneurial experiences were great learning opportunities (by which I mean utter commercial failures). So I responded by learning a variety of technical and then corporate and then professional services work until finally coming to understand that I really was the leader I'd been looking for all along.

Marty: Tell us about one of your more memorable business venture learning experiences.

Morris: Two friends and I put together a small Venture Capital fund, Biltmore Ventures. Since we were each entrepreneurs, we made half a dozen or so investments in very entrepreneurial companies like AdaptiveBlue, vSocial, and MyTrade. Intellectually we made a great team, one guy was a social networking mad genius and the other a brand marketing guru, but our operating styles were different enough that I realized I had to figure out how to unwind the new team.

Eventually I negotiated for the guru to own the firm and the genius to buyout the portfolio. Now we are each much more prosperous. You have to be open to new experiences but you must also honor peoples' inherent freedom to move on with their lives. In business, like everything else, you usually already know the answer before the question; it is just more obvious looking back.

Marty: What’s the most challenging aspect of being an entrepreneur from your perspective?

Morris: It is relating to non-entrepreneurs. Human value systems vary so widely that unless a person is, has been, or aspires to be an entrepreneur, it can often be remarkably difficult for them to understand your perspectives on life and living. Entrepreneurs, however, tend to view life with a somewhat broader perspective and therefore more readily appreciate a differing viewpoint. They are also more likely to incorporate this new viewpoint and run with it!

Marty: How has the business world changed since you first started?

Morris: In a hundred words or less?? Of course the easy answer is the Internet, which was born about the same time I was born. However, people already know the Internet has changed business. What is less obvious is that business has polarized just as much as other aspects of our collective cultures. People have changed.

Businesses don't make decisions, and neither do governments or any other groups. People make decisions and people have changed. Think politics. Understand that the core issue here is advocacy beyond the point of honoring sustainability. For example, Ayn Rand acolytes haven't learned that her thinking, while correct in and of itself, remains incomplete. Mutual alignment of self-interest only works when your thinking incorporates sustainability, otherwise you risk being a net-detriment to the world. In her defense, this is much easier to see now than it was 50 years ago.

Consider that Wall Street is no longer a meritocracy, that news is now merely perspective, that communication has become primarily about exchanging information. This is all survivalist thinking, but surviving is no way to live. Create, don't merely survive. Create and you could make a business that improves the world. Tell me about it and maybe I'll help.

Marty: What is a key personal attribute you see in successful entrepreneurs?

Morris: A willingness to be strong. Sometimes you just have to be strong. Sometimes that means the strength to be persistent, sometimes that means the strength to be accommodating, but it always means a willingness to be strong enough to rise to the occasion.

Marty: Any advice you would like to give to someone contemplating a startup?

Morris: Startups can teach you more about life than perhaps anything other than actual parenthood. Whatever you do, you will get experience and all experience leads to self-knowledge. The more you know about yourself, the more you can strive to be the best [version of you] you can possibly be. Along the way, be utterly candid about what you want and why. Ask others to help you with it. People love to help. Connect with people who are kind and smart, but above all, connect with people who are honest with you.

Everything else is just details. I'm @ http://www.callaman.us/ if you want to discuss details. I am looking for clients!

Marty: Morris, thanks much for your time and guidance, and for being a role model to the many budding entrepreneurs I know. We can all be inspired by your accomplishments.

Marty Zwilling