Risk and reward


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Happy Friday letter getters,
See that big Steadfast Media banner up at the top of our email? That's Michael Anderson's new business (and LaunchLetter's first sponsor!). Actually, I used to write about Michael and used to work for him, along with his three other cofounders at GameWisp (We covered fellow cofounder Eli Hooten in a previous letter). Now, Michael is starting a new venture.
This week's letter has an overall theme regarding risk and the power of believing in yourself. I used be fearless about risk. All the jobs I had were unconventional, outside of my comfort zone, and generally involved risky startups. I was comfortable with ambiguity, and learned how to be versatile. It wasn't until recently that risk became a little scary, because lately I've been feeling burned by it.
This LaunchLetter is a reminder that risk exists in life regardless of the situation, and it is unavoidable to some degree when starting or working for a business. The practice of putting yourself out into the world, even if it means experiencing failure, is essential to finding success.

Michael Anderson,
Founder, Steadfast Media


Michael Anderson has been solving problems with software professionally for over 15 years. After a bachelors and masters in computer science, he co-founded a software-based startup. As the founder of GameWisp, he worked closely with the technical team to develop the SaaS technology that enabled the business. After selling the technology that powered the GameWisp platform, he founded Steadfast Media in order to provide expert technology consulting to high growth businesses and help them solve hard problems with software solutions. The Steadfast team believes their experience through founding and running startups dramatically levels up their ability to provide actionable advice to, and targeted software solutions for, other businesses of all sizes. Meet your five minute mentor, Michael Anderson.

3D printing items from the soil and materials found around you. If we are going to travel into space and to other planets, we need to get better at leveraging the materials around us to create essential tools, habitats, and more. I'm interested in how people will solve these problems to empower the inter-planetary astronauts we will have in the coming decades.

The essential importance of doing the hard work to clearly establish your values, develop customer personas, and craft the early essentials of your brand as soon as possible in the life of your company. I cannot overstate how essential this process is to a business. I believe it to be as essential a process as is determining the problem / solution pairing that you are deploying to market. Really understanding your values and customers will provide you the lens through which you can select they type of business you want to take, determine the marketing messaging you use, and even help you understand who is a good fit to hire into your organization. Creating these north stars will help guide you in difficult seasons of uncertainty wherein you would otherwise have been lost.

I do my best to keep an updated list of tasks every morning. On my best days, I prioritize them based on a system of 4 categories: Important & Urgent, Important but not Urgent, Urgent but not Important, and Not-Urgent/Not-Important. It's easy to get distracted by things that are fun to do, but don't end up having any bearing on pushing your business forward. Knock out the Important & Urgent first, and then move on to the next section. At the end of the day (or the next morning), make a new categorized list including the remaining items plus anything that came up during the day. I don't always do it, but the days I do are super productive!

The startup mythology is full of stories of founders practically killing themselves with work and it leading to business gold. However, long hours and overwork do not necessarily produce the positive outcomes you may expect or falsely believe. There's a big pushback to focus on smarter work during a more reasonable set of hours (with good reason). That being said, I think that some important and transformative innovations take relentless focus, long hours, and extreme effort to achieve. It is essential that you are critical about the time and effort you spend on things. Do not work a million hours just because you think that guarantees success, but don't think that achieving big, complex goals can always be done without pushing your own boundaries and that of your team as well.

Mixing hard work, kindness, generosity, genuine interest in others, and humility lead to more rewarding successes than those forged through the mechanisms of fear, anger, ego, and impatience. We can often achieve more than our experience on paper would suggest, and believing in yourself to take the risk of attempting something new, while scary, leads to new lessons and further progress down the path to success.

Michael Anderson is the founder of a software development consulting services firm called Steadfast Media. He was also a cofounder of GameWisp.
Recent Achievements:
GameWisp recently had its technology acquired by another company in the space.

Let's talk about more risk-related perspectives.
I was browsing Twitter this morning and saw this tweet from Jason Stein (@jasonwstein):
"Whenever possible, get paid in equity. Take the risk of making less today for the potential reward of making a lot more down the road. This is the path to wealth creation. It's not easy, but you’d be amazed how much more you’re capable of when you have skin in the game."
Here's the link to the tweet:
https://twitter.com/jasonwstein/status/1140672985528971264
I was surprised at the number of people who backed his statement. After a personal experience, taking an equity-only deal seems like a horrible idea to me. I can't help though but read their perspectives and buy back into it just a little. The comment "Those who understand the game have a $1 salary," caught my attention.
What is your perspective on this kind of situation? As a founder, would you be comfortable asking someone to work for only equity? As a worker taking on an interesting project, have you worked an equity-only deal that has come to fruition? I have my own opinions, but I'd love to know. We might talk about it more on our Slack group this week. If you've read this far and aren't already in the group, you should be! Here's the link.
Speaking of our group, Slack is going public as a direct listing under $WORK.
I read about the benefits of a direct listing rather than an IPO in this article , and came to the conclusion that although there are key benefits to a direct listing, some might call Slack's play the more risky decision. From what I understand from the article, a company is best positioned for a DPO if they don't have an immediate need to raise more cash, have a household brand name, simple business model, and large shareholder base.
Here's a quote from someone who went from being a 46-year-old founder of a chat app to a billionaire this week. “By the time I finished my master’s degree I really had no idea of what I was going to do except for be an academic because, you know, the big five philosophy firms aren’t always hiring,” that's from Stewart Butterfield, CEO at Slack. I'd venture to guess he knows a thing or two about believing and betting on himself.
So the point of this letter is, risks present themselves all the time. Some are worth taking, and some are worth avoiding. It's up to you to make the decision. It might be worth it. Or you might fail, but not permanently. Success is only really dependent on your willingness to find a different way to solve a problem.

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Steadfast Media: Empowering Innovators to Achieve their Goals
Steadfast Media’s team has spent the past ten years as growth partners to both tech-enabled businesses and startups. We love helping all kinds of digital pioneers accelerate the pace at which they are reaching customers and audiences. Our unique experience has led us to offer supporting services for all types of businesses looking to grow their technology offerings, as well as leverage our unique experience as startup founders to accelerate your business in general.

LaunchLetter is a weekday newsletter from Southern/alpha, a website that features collections of stories and resources for underestimated startup communities.
LaunchLetter is for founders getting started on an idea or business. Our goal is to share the perspective, habits and positive messages of more experienced founders and CEOs. We hope you find it relatable and delightful as you get focused for the day on your own goals. Enjoy the ride.
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