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Using Sales As A Funding Mechanism with Casey Allen

BWP 11 | Funding Mechanism

BWP 11 | Funding Mechanism


Starting something small will only lead to something big if you have the right plan, right people, and right funding. In this episode, Casey Allen, commonly referred to as an ecosystem builder, shares to us how you can accelerate your growth in your perceived industry. Using sales as a major fund generator, he explains to us how he leverages investors to be part of his funding mechanism. For Casey, the key to any startup success is talking to the right decision-maker and conversing with the right investors. Thereby, interaction will always equate to growth. Moreover, Casey may be known for many things, but today, he is becoming more popular through the Enterprise Rising Conference held every year in Minnesota.

Listen to the podcast here:

Using Sales As A Funding Mechanism with Casey Allen

I’m very excited to have Casey Allen. I’m starting to hunt more of my guests and I’ve gone back to my network, someone that I’ve known for a number of years. Casey, welcome. Would you please introduce yourself?

I would love to introduce myself. I’m most commonly referred to as an ecosystem builder. I spend most of my hours and mental bandwidth thinking about how to build better founders, which then builds a better community. Founders in this context are tech funders, people building software companies that I’ve done most of my life. For the last years, I’ve been pretty heads down. Every day I wake up thinking about what I can do that helps them succeed with less pain. I associate a lot of pain with my entrepreneurial venture. Back in my twenties, there are processes that it needed to be. What drives me now is how do I make this lesson on less painful for other founders? If I can help one or two, then my job in life is done.

I first met Casey several years ago. I knew who he was because I was at a Gopher Angels meeting. I am here in town. It was one of the early meetings. My husband and I were both there. I looked around the room and talking about feeling a little out of place. There were not a lot of people under 50. There were not that many of us that were younger in the room. I noticed who he was and then I noticed he actually had an opinion. He would say something. I wouldn’t even talk about the reviews of the companies. Afterward, I asked my friend, Tim, “Who is that guy?” He said, “That’s Casey Allen.” I asked him, “Who’s that guy?” This was the start of how I knew who Casey was. Years later when I had my own startup, I go to Enterprise Rising.

One of the reasons I wanted to have Casey on is I like to talk about the stuff that people don’t talk about with startups. I want to dive into some of the areas where I wished someone would elaborate on a little bit more because I either didn’t understand or I didn’t know how to do something. Something I picked for us to talk about is one thing you posted somewhere. Later, I then saw a founder give you credit for suggesting to do this. I can’t even remember where I saw any of these. Probably it was in LinkedIn, but it was around this whole concept of as opposed to feeling that you have to raise a whole bunch of money to start getting some traction, it’s the idea of using sales as your fundraising mechanism. You are getting people to pay for stuff. I want to unpack that and have you talk more, especially for somebody who is an early stage, what might that process look like? How do you do it? What would you even say in that process?

I’m a big proponent of before you even run a line of code that you should attempt to get at least one customer, preferably two to four to pay you in advance for what it is that you are about to build for them. What you’re doing is you’re getting the ultimate validation. The ultimate validation is money. The pain that you think you’re going to solve is a need that is worth serving. That depends on what you’re going to sell. It’s not just that, “I’m going to build X and then you’re going to use it.” It’s, “I’m going to build X, it’s going to help you save a ton of money based on what you’re already using, and that you will be able to make that purchase.” Let’s say you’re selling to a business or enterprise, you need to make sure that they have the capability to buy it from you. They have the power to be able to make the next purchase. The price that you have in mind is one that is in line with what they think is fair or reasonable. They should have the ability to pay for it. Before any money code, try to pre-sell. The way this looks is not necessarily by being nosy. It’s not by sending out a bunch of tweets or writing a bunch of Medium posts, hoping people will magically find that and they will click on a link to send money. It’s about reaching out to people that you suspect or know will be your ideal user and having actual conversations with them.

We’re talking about real conversations with your folks. Having real conversations which means a 30-minute phone call or video conferencing call that you can use Zoom or whatever they use. If they’re in a big company, they might still use WebEx or Skype. The point of the conversation is to learn more. You’re essentially going to reach out and simply say, “I’m working on a product that will do X for Y. It helps this pain for these kinds of people. I’d love to hear your experience on what you have used in the past to try doing this thing or trying to solve this problem or pain that you have. I have got some very specific questions for you. Could you carve out 30 minutes for me sometime in the next month?” If they aren’t interested, they might don’t have this pain. You have to actually go back through and reassess, “Is it a pain that people have or am I just imagining it? Am I talking to the wrong kind of people?”

That’s what it made me think of, “Am I in the wrong market?”

Even if you don't give, you can extract a massive amount of value on Twitter. Click To Tweet

For example, a very common misconception in the world of tech startups is when you are building a product that you think is good for employees, it will be good as some employee perk or it’s good for their health or wellness. Oftentimes you will think, “I will sell it to the head of HR. If I can get to the VP of HR and pitch them on how great this is, then they will easily whip out the checkbook and pay me $15,000 a year for their employees to have access to this.” In reality, oftentimes that’s simply not the right decision-maker. The decision-maker is the CFO who’s going to take a much more clinical approach to this, an ROI-driven approach to it and also has a much bigger budget so that if he or she as the CFO believes this is good for the company, that it’s a good investment in their people, it’s a no-brainer to get ROI. Whether it’s retention or something totally different with productivity or minimizing how much lost time, then they will probably be the decision-maker and also be the buyer. The person that runs the HR does not have a budget. Sadly, if they do not have a lot of clout within the organization, that would be a huge waste of time.

Part of this task of pre-selling your software is also a test of, “Am I actually talking to the right decision-maker?” The conversation has to be pretty probing, almost therapeutic. It’s like, “Lay down on my couch and tell me all your problems.” A lot of the conversation you’re going to have is you asking questions and not pitching, not selling. It’s you asking very specific direct questions such as, “What do you guys use to do X, Y, and Z? What tools? What software?” Usually, it’s stuff that’s cobbled together that wasn’t actually built for it. Oftentimes you’re going to hear Microsoft Excel because that’s the ultimate Swiss Army knife. You are learning and you’re taking notes or at least you’re recording the phone calls with whatever conversation you’re having so you can review it many times over after it’s done.

You are asking tons of questions, “How much do you pay for it? How much do you think you pay per month? How much you think you pay per year? Is there something that came along that did it with less time or would you consider using them? Do you have a good mechanism in which to add users to this thing? Do you have a good mechanism to share the data that’s locked up inside this thing with other people? What does that look like?” You’re asking a bunch of questions almost like you’re an archeologist that’s digging nine layers deep to find Velociraptor bones. In this case, your Velociraptor bones is being inside the brain of this person. This is true, even if you are scratching your own itch that you have or once had, you cannot assume that everyone else has the exact same issue and looks at that the same way.

The reason why you need to be like an archeologist in this conversation is it is a build-up. This is the foreplay to then popping the question of, “I’m building something that will do all these things they just talked about. It’s going to do a checkbox, checkbox, checkbox and checkbox. We’re probably going to be charging $100 per user per month. We are on track for the product to be ready in,” and then say a timeline that’s actually way longer. “If you’re willing to be part of the beta, then I’m happy to include you at a discount. All I would ask is that you pay upfront. Are you in?” That’s a good sign if it goes over 30 minutes just like a job interview. This is called a customer discovery call. You can google this and there are some very good YouTube videos on how to structure these conversations so that you’re not inventing this from scratch. If your customer discovery call is done well, it is a very natural question to ask, “Would you want to be part of my beta and would you be willing to pay in advance?” Believe it or not, a huge percentage of people will say, “I’m in.”

If you can do this two to five times and get a bunch of people in, this comes to a couple of things. One, it means money in the door. As a founder in the early days, that is probably the second most important thing besides your knowledge. You need knowledge and money. Two, it validated that these people are serious about using your product. I hate to break it to the founders but when people say, “Your idea sounds amazing, I will totally use that once it’s done,” that doesn’t mean something. The fall-off is the amount of people that will convert down the road is extraordinarily, depressingly little. Talk is ridiculous to achieve. This is especially true if you are in an area like the Midwest where people will be polite even though their intent is not very high at all.

People that say, “We’ll totally us your name. We’ll buy it down the road when it’s ready,” that doesn’t mean you should discount on a zero. What is meaningful is are they willing to actually send you money right away/ If you somehow send over a link where they can pull off their corporate Amex card and pay you $500, $1,000 or $1,500 to essentially buy early access, you need to make it a discount so then they feel like they’re getting something and they can justify it to their boss if needed. You need to think about the narrative they have to tell their team or their boss of, “I paid $1,500 but they’re going to help us all this time around this pain.”

That pain needs to be big enough where everyone would think, “Awesome. We can’t wait. Thank goodness.” If done right after having the conversation, you will discover that the pain isn’t a big deal. What they’re currently using is actually pretty good. You learned that you actually have something resembling a competitor out there. That’s good. You need to learn this. Would you rather learn this now or would you rather learn it after you spent $100,000 in nine months of your life? Pre-selling is what the most successful founders I know do. There are a decent amount of blog posts and a decent amount of real-life case examples where hopefully you realize that this is very doable. Some of the best founders in the world do this before they spend money in any real-time building the product.

As you get into that process of pre-selling and discounts, what are typical discounts that somebody might actually see? Are they getting 25% or 50%? What would be normal? I want to know more.

BWP 11 | Funding Mechanism
Funding Mechanism: Marketing needs a very set amount of money otherwise, people will spend money until oblivion.


25% is a very decent starting point. More importantly, the psychological win on the other side of the table for the person buying it makes them feel good. They would feel that they did their company and their budget justice. It’s tough for anybody that’s never actually run a P&L but when you’re selling to somebody in a business, their budget is very sacred to them because the budget is probably going to get used up. There are battles over budgets all the time in big enterprise or even small enterprise. If you’re selling to a smaller business with 200 employees, there are very excellent points why they hired a COO or CFO. This person would say, “We need to create logic around how we allocate budgets. This department or division will get money to spend on this.” Marketing needs a very set amount of money otherwise, they’ll spend money until oblivion. You need to make sure that you’re treating that person’s budget with this level of sacredness that you would treat your own savings or checking account. 25% also has the added advantage if they want to push harder. They themselves are the negotiator. Then you can easily go up to 40% to 50%.

The goal here isn’t necessarily to maximize. You’re not maximizing for how big of a chunk of cash they’re going to give you. You’re optimizing for two things. The first one is to have skin in the game. The second is proof. Skin in the game means that down the road that much more likely to be a real user. They’re going to take the software seriously versus somebody who doesn’t have skin in the game means that you’re going to invite them to your alpha or beta and they will simply never set it up. They’ll never log in. They’ll never create their credentials. They’ll never populate it with the basic amount of data necessary for them to use this tool as it was intended. Keep in mind, the biggest barrier to every startup founder being successful is the customer using the software as you intended them to use it. Every founder would be a smashing success if everyone used their software, but that’s usually that’s not the case. Part of the way that you can do that upfront is by getting skin in the game. Number two is proof, just knowing that you are on the right road.

I have more questions. We’ve talked about the sales part, but speaking of sales. I’ve been thinking about that whole idea and some other things that you’re up to that I want to talk about. One of them is this startup job fair. I remembered seeing a tweet some time ago about, “There are these companies I met and you can come to this event.” Talk a little bit more about this because some people don’t even know about this and what you’re up to here. Tell us about the startup job fair that you started running.

Step one would be to get on Twitter. It’s in everyone’s best interest to create a Twitter account, even if you never tweet. If you simply go and create an account and follow 50 to 150 people that you trust, respect and you’re interested in what they’re talking about, you’re interested in what they’re sharing. Every Sunday, let’s say you spend 30 minutes just skimming your timeline like it is your own private customed newspaper, there is so much value to be ahead of us even if you don’t retweet anything or like anything. The amount of discovery and expanding your horizons that can be done in 30 short minutes is huge. I know not everyone from corporate is going to go create a Twitter account. Even if one of you does, I have no doubt it will improve the quality of your life.

What Amber is referring to is something that I did for fun several years ago. I ran an experiment. I do lots of crazy experiments that have absolutely no benefit to me directly. They’re not moneymakers for me. They are not bringing me fame, which is very important to me. I launched a job fair that was focused on some service. I know a lot of people when they hear the term job fair, they think of career fairs at colleges and universities. Let me shatter that image. Imagine showing up to a job fair in the evening, there’s techno music going, there’s beer flowing on tap and the energy level is very high. The only companies there are not boring companies, but the fastest-growing hottest startups in town. That’s the job fair that I created. I thought the community needed it and nobody else would do. I felt like I had to.

I launched and did this. We had an ad. We work Downtown Minneapolis, which is a coworking space. The environment was amazing and it was a success. I did a second one and it’s very easy for me to do because it only takes me a couple of hours. I sent out a couple of emails, make a couple of phone calls and a bunch of startups show up like we’re in. We need to hire four developers, two marketers and a product manager of staff. We need every advantage we can get. We’re in on the start chapter. They did a second and third one. After the third one, I realized that the hunger here was much stronger than I anticipated. The demand here was much stronger than anticipated.

I noticed a second phenomenon, which was the job hunters come from all walks of life. The cool thing about having a tech startup job fair is that the job hunters that show up are pretty self-selected to a very narrow path. They’re raising their hand and saying, “I’m interested in working for a tech company and I probably have some background check. I’m interested in working for a startup, so I obviously have some predisposition towards wanting to work for a startup, which hopefully includes from a risk perspective as well.” It is not anywhere near as safe a bet as working for Wells Fargo, for Nike or for KPMG. I was amazed at how many very qualified people showed up for the job fair. There are people that had many, many years of experience. This was actually my own journey of validation, even though I wasn’t asking anyone to prepay necessarily, but I ran an experiment. It didn’t take me a lot of time. It didn’t take me any risks and take me any money. I realized that there was a lot of hunger there. I understand not everyone could just pop up because you may not have the Rolodex that I built over the years.

The best way to change a conversation is to try to get people rallying around what you are actually good at. Click To Tweet

There are people who probably created a job fair that’s based on their tribe or their little corner of the universe that they do feel like they’re plugged into. I felt like this is something I had to take to the next level. In 2020, we will probably have two job fairs. The goal here is to help as many people as possible that are unhappy or don’t feel challenged in their current role. Whether you’re in a startup stage or you’re in a big company, how do I make it easy for you to discover and take the next step in joining a startup? Wherein you can feel more mission-driven and feel way more growth and have the time of your life.

I created the job fairs almost like they’re a landing page. I want to make it as easy as possible. If you are a senior engineer at Target or you’re a project manager for OPTiM or you are an iOS developer for Amazon. You may aspire to work or a smaller team or a smaller startup or you want to make a bigger dent, but you have no idea where to turn. You don’t feel like you have a good lay in the land or what startups in town, then there is the easy way to walk into a room, see fifteen startups that are all hiring like crazy. They are doing amazing things that are all between 25 to 300 headcounts. There is an easy way for you to start the dialogue. I’m hoping that this will be pretty transformational. I’m hoping to build the most effective bridge between talent that’s locked up in a much bigger company, specifically technical. It doesn’t have to be a technical talent. It may also be a salesperson or a marketer. Then giving them a very easy path to join a startup that’s 100 or 200 employees. That is an amazing thing. It truly transforms their careers and which hopefully it will also transform their lives. If you want to learn more about the startup job fair, you can go on Twitter and follow us. It’s @JoinAMNStartup. There we post a lot of announcements. You can also go to the website, to learn more about them.

This quite possibly is the biggest impact of anything I’ve ever done. I’ve run a decent amount of experiments in my life. I’ve watched an accelerator program here in Minnesota. I’ve watched the first true seed funding in Minnesota. I’m an investor in fourteen startups. I mentor hundreds more, but I believe that this might be one of the Archimedes levers that I can contribute that will have a pretty transformational impact on the startup ecosystem because I’m expanding the type of talents. It’s one thing for talent to move around from drift to when I work to dispatch and keep visible chairs. That might be good for the talent but it’s not necessarily good for the ecosystem as a whole.

The macro viewpoint of this is there are two ways. These are people that are locked up in big companies to do this in certain waters for the first time ever. Maybe they like it, maybe they don’t. At least they have a chance. Somebody has to be importing talent from outside Minnesota or outside the Twin Cities. I’m not in a position to do that. I’m focusing on what I am in a position to do. I am in a position to make joining to startup easier than ever before. I’m focusing on the Twin Cities, maybe different markets on the road. That’s something that I’m spending way more time on starting now. People will start hearing probably a lot more about it from November to January.

I would echo what you said about Twitter. It is interesting. It can go all sorts of directions, but I’ve always found it’s a fantastic funnel. It’s amazing who you can find and what you can find out. I’ve always enjoyed Twitter from that perspective. I’ve gotten connected with a lot of interesting people even via Twitter. Someone tweets or retweet someone I don’t know. I find them and that was how I met Nick White. You form almost like a system of trust. It’s someone you know that you retweet or that you send out. I have found it extremely helpful. I’m on Twitter and regularly on there as well. I echo what you say about getting out there and following people. What are people talking about? What are they saying? Where are things going to be headed? They’re very interesting.

If anyone is truly interested in growing as a professional, the only way you’re going to do that is by interacting and listening. You will not grow exponentially in your career by simply reading the same things and listening to the same 10 to 100 people that are either in your office or in your company or in your industry. By being able to create your own bespoke newspaper, which is Twitter, this is not about you tweeting out what you had for lunch. This is about you being able to, in one spot, in a very efficient manner, be able to skim and go deeper. If anyone says something, share something or there’s an important conversation thread happening on Twitter, you can then absorb and you can do it completely anonymously. If you really don’t want to be the person that’s on Twitter or putting things out there, maybe there’s a fear that you’ll put something out there and several years later it will come back to haunt you. That’s somewhat legit. At the end of the day, there’s so much value that can be extracted. Even if you don’t give, you can extract a massive amount of value on Twitter.

It’s perfectly acceptable to be a lurker. Lurkers follow things to see what they’re talking about. It isn’t in a creepy way, but it’s an information-absorbing way. I absolutely would agree with that. I have one more topic I want to talk about. We talked about things that are working on tech startups. One of the ways that we reintroduced after a gap of a number of years when I started my startup, I was like, “Casey’s got this Enterprise Rising thing.” I don’t know exactly what it is. You posted about it for a few years. I’d never been to it. I went to it a couple of years ago. Let’s talk with our audience about what is Enterprise Rising. That’s another passion project, another thing you work on and you put a tremendous amount of time and effort into it every year. Let’s talk more about what Enterprise Rising is and how that is evolving for you.

This went back several years ago. I was pissed off because I was hearing more people complaining about what we lack here in Minnesota or Midwest. At an event or some panel discussion, somebody would raise their hand inevitably and ask the question, “How can we be more like Silicon Valley?” It was at that point that I would want to get up and leave the room. It’s a very unconstructive question to ask. Nobody will ever be at Silicon Valley or at least not for the next 50 to 100 years. Silicon Valley is a true, unique anomaly and they’ve built something quite amazing.

BWP 11 | Funding Mechanism
Funding Mechanism: If anyone is truly interested in growing as a professional, the only way you’re going to do that is by interacting and listening.


The conversation around how should a city or region be like Silicon Valley is a complete waste of time. It’s a very poor question to ask. It doesn’t lead to anything truly actionable because nobody will ever be Silicon Valley, any more than Ann Arbor or Hollywood or Cleveland, Ohio or Wall Street. Hopefully, they don’t have those kinds of conversations because they too would be a complete waste of time and energy. You could be spending time and energy instead in the form of productive things. It’s a decent conversation to have rather than how can we be more like Silicon Valley, it’s how do we do with the Silicon Valley of X and pick something that’s very narrow that you already seem to have a competitive advantage in.

For example, you would be shocked to know that Fargo, North Dakota has a very rocking drone economy and drone community. Fargo is not a very big metropolitan city. It’s certainly not flush with a lot of funfair resources like Silicon Valley, which is tons and tons of money flushing around that’s going into high-risks with your startup. Fargo, in a very short amount of time, become a hub for drone technology. It’s a very worthwhile conversation to have with people that have real skin in the game or that can move the needle on certain things, “We seem to have this thing that’s naturally without us even trying hard taking off on this area or region.” It doesn’t have to be even technology. It can be like social ventures or it could be mental health. If there’s a region that wants to double down or triple down and make concerted efforts to be known for something to attract some of the top talents in the world, that’s something that’s a worthwhile conversation to have.

The best way that I knew how to change the conversation years ago was to try to get people rallying around what we’re actually good at. When you take a look at what excites you from a tech perspective, even though we have a lot of other things that succeed, we have lots of good food companies. We have a phenomenal med-tech industry. When it comes to software, what is easier? What gets funded here? What gets exited here? We have a lot of good and talented advisers in terms of that can help founders. It’s overwhelmingly enterprise SaaS.

Let me define the enterprise. Enterprise means we build software that we sell to big companies or big organizations. We will never create uploaded records. People can attack me for this, Minneapolis will never create the next Pinterest or the next Angry Birds. The likelihood that we can create the next Tableau or the next is quite high. We’ve got all the necessary ingredients. I wanted to try to get people talking about that, celebrating that and rallying around that and cheerleading that. I started a conference called Enterprise Rising. It gets together all the speakers. 100% of the speakers are all either successful enterprise founders or active investors that invest disproportionately heavily in the enterprise startups.

I’ve had my fifth conference in mid-July 2019. The conference is two full days and we have it in Minneapolis. It was at the TCF Bank Stadium, which is the stadium that the Minnesota Gophers plant. The speakers are amazing. I was very fortunate that all my speakers are great each year. We focused on two things. It’s helping founders meet the people that they need to meet. It’s about bringing people on stage that have earned the right to give advice. One of my massive pet peeves is the amount of people that are getting advice that they haven’t yet gone through the gamut to earn the right to give advice.

I’m very protective of who gets them on stage. As a result, the quality of the content is really high. It’s just from all over the Midwest, entrepreneurs and startups from the older Midwest. Hundreds of founders from all over the Midwest attend to it. It’s something that I hope outlasts me. I’ve built this conference for the next hundred years. Part of what I’m most proud of, for example the last conference, are a couple of things that I deemed successful. One of them is how many VCs actually fly in for the conference. That’s one metric. I also get excited on a personal note of how many investors flying and attended the conference that have never visited Minnesota before. Then it goes back to expanding the product. It goes back to how is the conference a platform to better our ecosystem. What is the best way that I can make the conference platform to better the ecosystem is bringing in people that may not ever come and visit so that founders can meet them, leverage them and perhaps get funding from them if that’s important to them. They’re getting mentored by them if that’s important to them, perhaps partner with them in some business. Any way that I can do that with the conference, that’s what drives me to keep doing this every single year.

Talk about where you want to go in 2020 with the conference. Sneak peek on everybody, what’s on Casey’s mind?

Anybody can learn more about it at The website and the dates for 2020 are locked in for mid-July, although I haven’t added speakers yet. There are two different things I’m interested in adding on to the conference, that if people have attended in the past, they might notice. Number one, I want way more startups from the Midwest further than 500 miles from me. There are a bunch of rocking startup communities honestly that I want to attract more founders from different places. That’s going to be a concerted effort. There’s way more of a melting pot of the Midwest than ever before, which is right now, it’s St. Paul and Chicago-centric heavy and I want to expand that.

You will not grow exponentially in your career by simply reading the same things and listening to the same 10 to 100 people. Click To Tweet

Secondly, something that I tried was I rolled out a diversity program where I sent to fifteen founders to the conference for free. This is a free $200 pass for the full two-day conference. If you were a female founder or a founder of color or LGBT founder, you could fill out a short form and you are in. That was something that I was very proud to do it. It takes a little bit of leg work. Honestly, it’s bad for my finances but I think it’s good for the overall ecosystem. It’s incredibly good for those that participate in it or take advantage of it. I’d fully realized that as a white male, I’m somewhat a suspect whenever I talk about anything diversity-related and roughly so. How could I possibly know what it feels like? The world was built for me.

Never ever in my life do I have to worry about it or have I been worried about walking into a room that was focused on tech and I feel like I didn’t belong. You definitely know what I’m talking about if you are a female or you are of color. You definitely feel like you stay down. You feel like you look around and there are not many people that look like you at all. It’s friction. At the end of the day as a white guy, there’s not a lot I can do to change how many people are in tech per se. I do not control who decided to get into tech and who decides to be cofounders. What I thought about was that there are some levers that I do control. As an event organizer, what levers do I control? I control who’s up on stage. I work hard. At the last conference, 50% of the speakers were not only dudes. I measure and that is one of the KPIs. In fact, it keeps me up at night the most when I plan every single conference every single year. I’m working hard to make sure that the stage or the amount of speakers over the two-day conference is not dominated by white guys. It’s really hard.

It’s not impossible. It just takes more work for me. It also takes a different work for me in terms of recruiting speakers. As far as I know, I don’t know of any other tech conference in the Midwest that actually turned his money for people to attend that has a speaker lab that’s 50% non-white dude. It’s something I’m fairly proud of but I keep working harder at it. That’s one lever I control. If I was a black woman in tech for a woman, and if I took a look at a speaker lineup on a conference site and it’s all white guys, how motivated would I feel? Even though I can’t possibly put myself in her shoes, I can try or attempt to imagine. I would feel there’s no effort to make people like me being a black female founder. The question of feeling welcome is what I think about, “How do I roll out the red carpets. How do I make it as easy as possible for a female founder, a founder color or LGBT founder to feel welcome in that room?” I control who’s on stage so I’m going to.

Number two, I can roll out a red carpet in the way of saying, “I understand not everyone is in a position to pay $200 to attend the conference.” As a founder, there are always trade-offs. This may not rank a high for you, but could I help it rank a little bit higher if I just remove that price entirely? I sent fifteen founders to the conference for free. Next time, I’ll send 50 to the conference for free. I’m super excited about that actually. It’s something that I spent almost all my time thinking about on how to pull that off. I’m talking with a handful of a bunch of bigger companies that might be willing or interested in sponsoring that being done. My first-ever diversity sponsor and underwriting that and making that a reality. What I’m actually hoping to do is take it one step further, not just hook up a diverse founder with a free ticket to the two-day conference, but also to comp their hotel for three nights. Free hotel, free admission to the conference, meet amazing people, learn awesome stuff from people and hopefully take you start of the next level. I’m trying to find a corporate sponsor. As you can imagine, I’m running my own enterprise sales process in and of itself.

It’s always going to be a decision by committee. I’m talking with some much bigger companies, but they’re very slow going and it’s in very early talks. I welcome conversations with any company that wants to plant a flag in the ground. Diversity in tech is good. We want to play our little role in trying to make that more and more of a reality. We want to make it more real so that Amber Christian can walk into a tech conference and look around to see more than one or two other females like herself. Thus, feeling more welcomed, feeling like she belongs to us, feeling like she’ll want to attend more. Thus, feeling like the community is far more welcoming and accessible to her. I’m looking for any company that wants to partner with me on this and join me on planting this flag in the ground. This is especially true if any company actually has startups as a customer base or a customer base they want to go after. It’s a double win for them. It’s not just good for the world and also good for technology but it’s also building a pipeline of their next customer base that is coming to fruition.

I would add to that. Casey and I have been having a dialogue about it for a couple of years. I went to Enterprise Rising a couple of years ago. I was intimidated by walking in and finding a room that didn’t look like me. I’m used to that, I have been in tech for a long time. It can be a barrier, getting more people there that look us and the diversity of ideas we bring. It’s the different ways that we look at things. There are more benefits than the fact that there’s another gender there. It is our thought process. It’s the things we see in other people’s businesses that you don’t see.

That’s part of what’s so beautiful about bringing more diversity of inclusion in there. Especially for a lot of my friends in the corporate, people ask me fairly frequently, “We love seeing what you’re doing, but we can’t buy. We’re not in control purchasing but how can we help?” If you want to help me, you sponsor someone to go to Casey’s conference. Sponsor a diverse founder, an underestimated founder, another female founder to go so that my community looks more like me and is more diverse.” That is the best way that anybody can help those of us that are in the trenches. When we find each other, we create stronger networks because everybody gets a better network and more ideas from that. They can sponsor one, right?

Yes. I’ve had that as a ticketing option. When you go to buy a ticket, there’s a menu of different types of tickets that pop up. That’s halfway there. If you want to send me up a note or particularly either right through the website, there’s a button that says email me or contact the organizer or reach me through LinkedIn, send me out an email and simply say, “I bought the five entrepreneur tickets.” If possible, if you could try to give them away to whoever it is that you would get great emotional fulfillment. I see all those female founders, maybe they’re the students. It’s a way for you to play your little role as somebody backing some other founders that are trying to do their own thing and are trying to change their world in their own way. It’s a way for you to almost like a donor chooses a model where you can easily buy the tickets with one click. Then reach out to me and let me know who you want me to give them to. I’ll make sure it happens.

BWP 11 | Funding Mechanism
Funding Mechanism: Diversity in tech is good. We want to play our little role in trying to make that more and more of a reality.


I’m excited to see where this goes. I’m excited about Enterprising Rising. Casey, how do people find out more about you? What if they want to connect with you, follow you? Where do they find you on social media?

Before we get to me, I want to check with you. What were one or two talks from the Enterprise Rising conferences that you attended that specifically resonated with you?

Sherry Walling of ZenFounder. I love the fact that she talked about life. It wasn’t just about running the business. We acknowledge that we have lives and things that we have to take care of and how emotionally difficult the founder journey is. For me, what was the absolute top one.

I had invited a couple. The husband is Rob Walling and his wife, Sherry Walling. Rob is a successful founder himself. He founded a company called Drip built into several million in revenue. He sold it to another company called Leadpages. His wife, Sherry is a PhD. She’s a therapist and most of her clients are entrepreneurs. Not only was she married to an entrepreneur and had to ride that roller coaster because no matter what, a founder’s spouse or significant other is definitely riding in that world. They are with them whether they want to or not. We had two different perspectives, which was amazing. They talked about stress, anxiety and burnout. They talked about how to keep your marriage intact, how to be the parent that you want to be all while riding this crazy roller coaster called your startup. The amount of feedback I got from founders after that had way surpassed my expectations.

Hard skills are one thing and you can hunt them down and find all of them. There’s a lot more to it than that. For me, that’s been extremely important too. It was like, “I don’t want my marriage to die because I’m running a startup. I don’t want to lose track of family and friends because I’m running a startup.” Even just balancing that, it’s nice to see people acknowledge it because I’ve heard founders talk about I didn’t and things that have happened. It was nice to hear it a little more upfront and earlier in the journey and things to think about. That was a great session.

For the readers who want to learn more about that topic of how to keep her sanity in your personal life and in your relationships while running or starting a startup, there is an interesting podcast where an entrepreneur interviews entrepreneurs about being a parent as well as being a founder and CEO. It is very insightful and very good high quality. It doesn’t apply to dads or men. It can also be applied to moms or females. This is not a topic that’s talked about at all. We don’t talk about anxiety and burnout. We don’t talk about failure. We certainly don’t talk about work-life balance. It doesn’t mean anything anymore, but it’s talking about how to stay moderately high-functioning in both your personal life and your founder life. The stuff is not dissected and real stories aren’t shared enough. As a result, there’s this way more pain and turmoil and broken marriages and unhappiness that I think there needs to be.

Tell us more. How do they hunt you down? Where do they find you? When they start lurking on Twitter, where will they find you?

The landing page for me is on a thing called AngelList, There you can find a way, then you can find me on Twitter. You can also read a little bit about me. You can see the investments that I’ve made, it started in the past. I’m not investing right now. I stopped or I hit pause on all new investing a few years ago for various reasons. I also made a critical promise I made to my wife. That’s a promise. There will be a day that I will start investing again. I don’t know exactly. It’s something that I feel like I can help serve others in so many ways besides writing a check. You can also find ways to reach out. My DM is open on Twitter. Anyone can just send me a direct message on Twitter. If you have any questions or you need help with anything, feel free to reach out.

To the audience, thank you for joining us. Don’t forget to rate me on iTunes and Google Podcast. I’d appreciate it if you’d give me a rating there. Now, you know what time it is. It’s time to go be wonderly.

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About Casey Allen

BWP 11 | Funding MechanismCasey is known for many things. He’s run several startups of his own, an accelerator, and been a podcast host.

Today he’s known for the Enterprise Rising conference held in Minnesota each year.

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