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$100K Investment from Outlander

Outlander Labs held a virtual pitch competition today. It was an opportunity for innovative startups in the Southeast to compete for a $100K investment. Lots of great applicants were whittled down to these six finalists:

  • All Access Advance – Nashville, TN – A platform for managing touring artists, venues, and events in real time from a single dashboard
  • City Shoppe – Austin, TX – A two-sided marketplace and software platform that helps consumers “shop their values” and helps local brands and retailers get discovered and reach a larger audience
  • Linguix – Miami, FL – An AI-based writing assistant and language learning engine
  • OrderNerd – Atlanta, GA – A platform for restaurants that consolidates third-party online ordering platforms onto one pane of glass
  • Prospectus.ai – Charlotte, NC – A sales intelligence tool designed to create an internal relationship graph that companies can leverage by making introduction requests that will generate warm leads
  • SportAI – Birmingham, AL – A mobile app integrated with AI that optimizes your fantasy sports lineups and, more importantly, helps anyone understand fantasy sports

The founders did an outstanding job pitching, and I enjoyed hearing about their companies. Can’t wait to track these companies—I’m sure they’ll all do amazing things.

It was a tough decision, but I’m happy to announce that City Shoppe was the winner! Congrats to City Shoppe and to the other founders for building interesting companies.

Putting Pride Aside When Making Tough Decisions

I had a very interesting conversation with a successful founder. He accomplished what a lot of founders aspire to: he sold his company for a significant amount. He’s had time to reflect on the journey, and I was curious to pick his brain. When I asked him about the most pivotal decision he made, he replied, “Putting my ego aside and stepping aside.”

This founder built the company over a number of years. Eventually, he noticed he wasn’t as effective as he’d once been, and over time he realized the company might be better served with someone else as CEO. The decision wasn’t easy, and he struggled with it for some time. Ultimately, he replaced himself with another CEO (with the board’s approval). He took another leadership role in the company that was product-focused. Fast forward a few years: the company was acquired, and everyone was happy.

Hearing this founder describe his decision was engrossing. He clearly had a strong desire to be the leader. He also wanted what was best for the company, though, and that attitude won out. He put his pride aside. The end result confirms that his difficult decision was the right one.

Long-Term View

When I read about a new indoor entertainment venue that recently opened in Atlanta, I called a friend who lives in the area. He said the venue is doing well—he often sees a line of customers waiting to enter. I drove by this weekend and saw the line for myself. Opening this venue was no small feat. It required tons of construction. It must have been preceded by years of planning. And given that it just opened, I assume the owners decided to push forward during the uncertainty of 2020.

Last year was a once-in-a-lifetime circumstance (hopefully) and one of the scariest situations a lot of entrepreneurs will face. But on a smaller scale, short-term changes in the market and unexpected hurdles are common. If founders focus on what’s happening right now, they’ll constantly be changing their plans.

The successful founders I know have taken a longer-term view. They decided where they thought the world was going and developed a vision for how their company fit into this future. They were heads-down focused on turning that vision into reality. They powered through short-term ripples in the market, always believing in their longer-term vision. Not over-focusing on the short term was the right call and these founders built great companies that went on to do great things. Often, others couldn’t see it and thought they were crazy for bucking current trends. They didn’t care, stayed the course, and were proven right.

I don’t know the owners of this new venue, but I imagine this describes them. After all, they chose to continue building an indoor venue in the midst of a pandemic!

If you’re an early founder or considering becoming one, be mindful that success will come from taking a long-term view of where the world is going, not reacting to daily changes.

Founder Motivations

This past week I spoke with a founder about his company. When I asked him about his why, he said he wants flexibility for himself and his family. He’s excited about what he’s doing with his company, but he’s passionate about changing his family’s circumstances. He wants to be able to make decisions without factoring in money and have control over his time so he can spend more of it with his family.

He isn’t the only founder I’ve heard this from. I spoke with another founder who raised nine figures in venture capital. He’s passionate about the problem his company is solving and equally passionate about the financial freedom it’s afforded him. He now wants to invest in early founders who are motivated to build companies because they too desire freedom.

It’s interesting to hear about founders’ motivations. The desire for a better lifestyle for yourself or your family can be strong and lead you to build a large company. I think the trick is identifying the right problem to solve. There are lots of possibilities and picking one you’ll stick with through the ups and downs is important.

Whatever your motivation, make sure you’re clear about it going into your entrepreneurial journey. If you don’t know why you’re doing something, it can be difficult to do it to the best of your ability.

Borderless Recruiting Is Tough for Some Founders

I connected with an early founder I’ve known for a few years. He recently completed raising a round of venture capital and is excited to get back to building his company. We talked about all the things that are top of mind. Naturally, recruiting headed his list. He finally has the capital to hire the people he needs to support growth. Unfortunately, he’s facing something he hadn’t planned on. “Recruiting in this work-from-home environment is hard. I can’t afford anyone.”

This founder is in a second-tier city where salaries are historically lower. His fundraising assumed that he’d pay market rate for new, local hires. But the work-from-home movement hasn’t eased, and it’s hindering his recruiting efforts. He finds himself in a situation where he’s competing not just with other local companies but also companies nationwide. Some larger companies are offering salaries and benefit packages he can’t come close to. This wouldn’t have mattered before, because these companies used to want their people to live near the mother ship. People who didn’t want to relocate often took jobs that paid less. Now, larger organizations are allowing employees to work from home, which has expanded the reach of their recruiting efforts.

We’re in a very early phase of determining what work will look like going forward. It was interesting to hear a firsthand account of how it’s affecting one founder’s efforts to build his team. I’m not sure how this will play out, and I’m very interested and will be watching it closely.

Consulting Can Uncover Big Opportunities

I’ve known a few founders who’ve built interesting products because of consulting. A consulting engagement usually includes a discovery process that will help the consultant understand the business or process before they make recommendations. This can lead to the consultant seeing that there’s a big opportunity they’d like to be part of. These savvy founders then build a solution to solve the problem and then productize the solution, by arrangement with their consulting client.

I recently connected with a founder who’s taken this path. The pitch began with an intro to the problem and the solution he’s built. Over the course of our conversations, I learned about his consultancy and decided to dive in more there. I realized that the product he’s pitching addresses a small part of the larger problem he’s solving with his consultancy. I suggested that he lead with the larger problem and how his consultancy has positioned him to be uniquely qualified to solve it. He has an understanding of the space that’s much deeper than most people’s.

I can’t say if this company is a good candidate for venture funding, but I think the founder has found a large market that’s likely to continue rapidly expanding. He’s in a unique position and has an opportunity to build a big business. Can’t wait to see what the future holds for him.

Where Are the Women’s Liquidity Events?

I shared my excitement about where Atlanta is headed in this post over the weekend. I’m excited to see numerous founders complete eight- and nine-figure liquidity events. I’m even more excited that they want to give back and help emerging founders. And I keep thinking about this founder group.

From a race perspective, Atlanta is unique, and I love that. A group of diverse (non-white) founders have sold their companies or raised funding rounds of eight or nine figures. That’s huge and a testament to what makes the city special. I personally know some of these founders, and it’s an amazing thing to see up close. They’re inspirations to so many other founders of color not only in Atlanta but around the country. In Atlanta, they help provide much-needed proximity to success for diverse founders. I have no doubt that their success will lead to many others being successful.

It struck me, though, that I know of only one female founder who’s exited or raised eight or nine figures. I can name a few men who’ve done it in the last eight months, but women? One in the last 5 years. I reached out to an investor and founder to find out if I’m missing something or just out of the loop. They both confirmed this is likely accurate (although a few women have raised seven figures—I commend them!). Atlanta is full of amazing female founders, so this realization is extremely disappointing.

People way smarter than me have put in years’ worth of groundwork in Atlanta to address this problem, and I salute them for those efforts. I’m looking forward to being part of the solution as well and can’t wait until Atlanta’s female founders are experiencing eight- and nine-figure acquisitions or capital raises!

Don’t Be Afraid to Share Your Big Vision

I met with a founder who’s building an interesting product in the real estate space. Toward the end of our chat, I asked a few questions about his big vision. The conversation took another direction. He opened a document he’d created for internal use. It highlighted where he thinks the industry is going and a comprehensive platform that would support the industry’s new direction and change the landscape. The product we had discussed at the beginning of our meeting was a small piece of this comprehensive platform.

This founder has a big vision and strong opinions about where he thinks this market is headed and the problems he sees holding the industry up. But he didn’t lead with his big vision or the big problem —he just mentioned them in passing toward the end of his pitch. Understanding his big vision was a game changer for me. It got the wheels in my head turning —I realized he could fundamentally change real estate if he’s right.

Sometimes founders are gun-shy and don’t want to share their big dream or vision for fear of scaring investors off. So, they share only the first step. I’m not a fan of that approach. I think founders should be open and share their big visions and the first steps to making it a reality. Sure, some people won’t agree, but that’s OK. You’ll likely get interesting perspectives that will be helpful, and you may even find someone who buys in and wants to support your big dream.

If you’re an early founder, dream big—and don’t be afraid to share those grand dreams with others!

Atlanta’s Finally Got the Missing Ingredient

Over the past eight months there have been a number of sizable (eight- and nine-figure) liquidity events for Atlanta startups. Companies have been acquired by larger companies or private equity firms or have raised a round of funding from venture capital firms. Many of the recent transactions have provided cash to founders and other early employees.

I was catching up with one of these founders yesterday. His company completed a nine-figure transaction. He told me all the ways he wants to help emerging founders. He has some great ideas about how to prepare founders for the ups and downs of the journey. He had his own early challenges obtaining capital and now wants to start investing in emerging founders so they don’t have to experience what he did. I’ve heard four or five other founders express similar thoughts over the past few months. It seems to me that Atlanta’s ecosystem is about to skyrocket.

One year ago, almost to the day, I shared my thoughts on what was missing for Atlanta entrepreneurs: more large liquidity events. Now, one year later, the city has experienced such events and they’re having the effect I predicted. Founders and other beneficiaries of these transactions are investing cash in early startups. And they’re sharing the knowledge they amassed during their journeys. Both are huge pluses for early founders and will do wonders for them, including helping to accelerate their success. As more startups are successful, more investors and talented people will be attracted to the city.

We’re in the very early stages of the impact these liquidity events will have on Atlanta’s startup ecosystem. I see big things on the horizon. The startup scene in Atlanta is about to reach a level we’ve never seen before. Buckle up! It’s going to be a fun ride!

Alternative Asset Classes

I’ve always been a fan of nice shoes. There’s an old saying: when you look good, you feel good. I think shoes are a big part of that. Shoes have transcended their purpose as foot coverings and become an asset class. And marketplaces like GOAT and StockX have helped illuminate just how much enthusiasts value shoes.

This got me thinking more about alternative asset classes. I’d imagine there are other tangible items that are prime to be turned into an alternative asset class. Their intended purpose at creation was X, but people now place more value on them—to the point that they don’t plan to use them as X. Instead, they’ll prize them for their monetary value or put them on display, or both.

Lots of items have been turned into alternative asset classes already (think art and wine), but I believe there’s a second-wave opportunity. Somebody with vision just needs to recognize a category of items that’s never been thought of as an asset class but that now resonates more with the masses or perhaps with younger generations and that owners value immensely. When they do, they’ll have a big opportunity to help owners legitimize the category as an alternative asset class.

If you’re a founder and passionate about something you own, consider solving this problem for yourself and others. It could be a huge market.