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Jason Weaver, founder & CEO of AirDeck, knows how to zero in on game-changers. He also knows how to take a concept and build a successful business around it. AirDeck is Jason’s third startup. He previously built and successfully exited Shoutlet and Spendship. He’s also a high-profile consultant, an angel investor, and a prominent author.
This time, he’s focused on presentation software. AirDeck is a fast and easy way to add voice or video to any document or presentation. It allows the user to easily edit each page or slide separately without needing to use a separate video editing tool. Its users are trainers, educators, marketers, lawyers, and frankly, anyone who wants to narrate a presentation or document so that the recipients can understand the context, on-demand.
Jason joins The Savvy Entrepreneur to tell the story of how he decided to start AirDeck. He shares how he found funding, and tips for staying sane while building a fast-growing startup. His candor and humor make him relatable. His formidable track record of startup success, along with his numerous other accomplishments, make him a force to be reckoned with.
What follows is a transcript of that interview. But if you prefer to listen, you can access the podcast here.
Doris Nagel 0:42
Hello everybody and welcome to The Savvy Entrepreneur show. We’re broadcasting from the Greater Chicago Milwaukee area.
If you’re an entrepreneur or small business person, this show is for you.
I’m Doris Nagel, your host for the next hour. I’m a serial entrepreneur, and I’ve also counseled lots of startups and small businesses over the past 30 years. I’ve seen a lot of mistakes, and I’ve made plenty myself. I’m driven to help others avoid some of these pitfalls and be more successful.
The show has two goals: to share helpful information resources, and to inspire — to make your journey as an entrepreneur faster and easier, and maybe just a bit more fun!
To help with that. I have guests every week on the show who are willing to share their stories and their advice.
This week’s guest is Jason Weaver, the CEO and founder of AirDeck. AirDeck is a company that allows you to create distributed and track narrated presentations. Its users are recording things like on demand webinars, personalized a sales presentations, creating employee onboarding guide, sending investor pitch decks. Frankly, almost anything that you can think of that is used for PowerPoint presentations or precede eggs or other kinds of presentations to communicate with other people. AirDeck, Jason says, is much easier to use than creating videos and everybody knows how important video is for today social media. And he says it has better tracking capabilities.
Before I share Jason’s biography, I have to warn you that he is one seriously accomplished human being. He’s a prominent author and thought leader in product innovation, digital marketing and entrepreneurship. Prior to launching AirDeck, he founded and successfully exited from two other technology companies, including Shoutlet, a social media management platform, and Spendship, a mobile loyalty platform.
He’s authored numerous articles for publications, including Forbes, Mashable, and Bloomberg. He’s a frequent speaker, and his book Managers Guide to Online Marketing has become a go to guide for companies. Jason has raised over $50 million in venture funding for his companies. He’s also an active angel investor.
He also works as an advisor for several emerging technology companies in the likes of Emma, Live school, Venture 360, and Directly. In addition, he advises both venture capital firms and network Angel funding groups. And he’s been a technology advisor to some of the world’s most recognizable companies, just to name a couple in a very long list, eBay, Miller Brewing, American Family Insurance, Best Buy, IKEA, and Nissan, to name just a few.
Jason, with all your accomplishments already, it sounds like you must be about 80 years old!
Welcome to The Savvy Entrepreneur Show – thanks so much for joining me!
Jason Weaver 4:09
Thank you for having me — I’m excited to be a guest here. It’s funny when you say it must be eighty years old. I always say when you’re in the startup world, you work in dog years — seven times the speed of normal companies. Sometimes I feel like I’ve aged a lot, but no, I’m not that old!
Doris Nagel 4:27
No, I saw your headshot. You don’t look close to 80. I’m just teasing you! You have an amazing list of accomplishments.
And I’m really honored today to have you on the show. The place to start I think is with your current venture, AirDeck. Tell us a little more about AirDeck.
Jason Weaver 4:53
AirDeck is just coming up on our first year in business. It’s an online platform that allows you to walk anybody through any document or presentation using your voice. It’s really taken off, because you can imagine when you’re sending PDFs and PowerPoints and things like that to people, you really lose the context behind it – to able to explain it.
And the other thing is, we live in this world of asynchronous communication. I can send an email and reply back in my own time, or slack message, etc. But we still have a lot of Zoom meetings and live stuff. When you can’t have those live meetings, there’s no next step, besides just sending over a PDF or document.
So we invented AirDeck because it allows you to add voice or video to any document — so you can explain yourself as you’re walking through things. And it’s been used for numerous business cases as you outlined at the beginning of the show.
Doris Nagel 5:52
There are other ways to narrate PowerPoint slides and other documents. What’s unique about AirDeck?
Jason Weaver 6:04
It’s a combination of things that makes it unique. That’s how AirDeck started, by the way – I was narrating PowerPoints with the built in recorder and sending that out to people.
But I had challenges with file sizes being sent. I wasn’t able to track what people are viewing. I wasn’t able to put much interactivity into it to keep those documents to make them engaging for the people that were receiving it.
AirDeck is a SaaS platform, meaning Software as a Service online-based platform. And we built into our platform a lot of those features I just mentioned that keep your documents engaging. People can walk through your document or presentation and you can measure what they’re looking at while they’re viewing it. It’s a combination of all those things that makes AirDeck truly unique.
Doris Nagel 6:45
How does AirDeck track engagement as people go through, for example, the slides in the deck or slides in a webinar presentation?
Jason Weaver 7:01
You upload your files and record directly into AirDeck’s cloud platform. AirDeck allows you to have complete control of your content. So as people are viewing your content from our cloud servers, you can turn on and off content, even after it’s been shared. I can update content, even after it’s been posted on third party websites or in social media. So it gives you a lot of flexibility.
AirDeck – unlike video recordings — allows you to add voice or video to a document one single page at a time. So you can quickly update stuff when you need to.
You can certainly record it on a platform like a Zoom using video. But if you need to make a change, you have to record that entire video again. With AirDeck, you can change just one slide or one page , or one segment.
So AirDeck gives you a lot of flexibility and efficiency, and additionally allows you to add a lot of personal touches to presentations and documents. Our AirDeck customers are sending files that seem like they’re speaking directly to their customer or client. The recipient might get a presentation that says, “Hey, Doris, this is a presentation that we went through today. Here’s what we talked about on page three.” That’s opposed to talking AT customers, which a lot of people do with video.
Doris Nagel 8:15
I do on demand instruction for an online training company. And I actually have to update actually a couple of my courses. Is that something I could AirDeck for?
Jason Weaver 8:40
I think you’d love it for that.
Doris Nagel 8:44
I’m pretty sure I would. You may have a new customer! But I’m curious how it works from a search engine optimization/SEO perspective? Do the Google algorithms treat this like video, or not video, or something else?
Jason Weaver 9:04
I think it’s even a little bit better than the video again a video you’re kind of locked into things unless you can add things like closed caption and descriptions that can be searchable through Google search.
Video has some inherent flaws. I mean video is awesome for engaging and telling a story. But when you don’t have a production crew or time to edit and produce, AirDeck is a good option for most people. You just upload a document, add voice on top of that document and send it out.
Regarding SEO, we live in this world of social media now. We’re constantly using our own platform to post on LinkedIn, Facebook, and Google, and then we add hashtags and keywords and things like that around our presentations that draw people to it. It works very effectively for us.
Doris Nagel 9:50
You’ve done a lot of things already very successfully in your career. What made you decide to start this business?
Jason Weaver 10:00
I did have a lot of other things in mind. It was through another idea that this came about.
One day, I was putting together an investor presentation. And I knew that I wanted to meet with, l say, 100, angel investors and go and pitch my business idea to them. I had a specific business idea in mind, and I put it together great presentation.
But then I realized there’s no way that I would be able to have an individual phone call or webinar with all these different investors to pitch my idea. I needed to hit a bunch of them at once and gauge their interest.
So I sat down and did exactly what you talked about. And I recorded a PowerPoint presentation, adding audio to each individual slide. The only option back then was for me to export it as a video file. And then I sent that video file out, and I hit those 100 angel investors.
And almost all of them wrote back, asking me how I put that presentation together. They weren’t commenting that they were interested in my pitch idea.
I thought that was really interesting. And that’s how I knew I was onto something. I searched online for on-demand platforms and ones that can be done asynchronously. And there weren’t a lot of options. You can kluj together a solution and create something suboptimal You can put together a video. But then if you make a typo at the end, like I did, you can’t update it. You have to record the whole video again.
Doris Nagel 11:25
Well you can, because I’ve done it. But then you have to be able to use video editing software, like Camtasia, which I spent a long time trying to learn. It’s very useful, but you have another piece of software then that you have to mess around with.
Jason Weaver 11:47
Yes, it is possible. You’re absolutely right. I use Final Cut Pro. And there’s lots of options out there.
But for the average user, right, average marketing manager, average salesperson average teacher, they’re not video editors. You and i can do that because we’re in the production business. But it’s not easy for most people to work with video.
So AirDeck provides an alternative to them – one that’s as powerful as video, but as easy to edit as PowerPoint. You can sit back and watch an entire air deck presentation play through, just like you’re watching a video, but the viewer doesn’t know that behind the scenes, I can update that presentation in seconds.
Doris Nagel 12:28
That’s amazing! So how did you get started? You had a an aha moment after sending out this deck to 100 angel investors, but what happened next?
Jason Weaver 12:47
I knew I was onto something. And I was fortunate to have had a couple of prior exits. So I seeded it with my own money in the beginning. I talked to a couple friends of mine that were developers and said, “Hey, you know, can you give me a good deal on developing this idea I have for a SaaS based online platform. I want to try it out and just test it. Something in my gut is telling me this is going be pretty cool.” And they got behind it — they liked the idea a lot.
So we built it, and then we played around with it for good five, six months. And then I gave it to a few of my friends that had become CEOs at other software companies and got their feedback.
And they gave me some remarkable feedback. We added surveys to it. We added hyperlink tracking to it. We added collaboration where a team could work on something together. I didn’t think of any of those things when I first built it. So all the feedback we got at the beginning was invaluable.
As for how and when I decided to make it an actual business, I have to give credit to Dave Trotter, one of my first investors. I was meeting with him about other companies. And he asked me, “What are you, Jason, working on today?” And I showed him AirDeck. And he said, “Holy moly! This is awesome. You know, I would invest in this if you really wanted to make a business out of it.”
And I said, “Well, I have a few hundred users now. But I could…”
Doris Nagel 14:05
Wow, that’s amazing. An investor who tells you, “Hey, if you decide to make it a business, I’ll fund you.” I mean, most entrepreneurs are running around with a little tin cup, just trying to get two minutes of an investor’s time. Unbelievable.
Jason Weaver 14:22
I think I had an unfair advantage because we had a big exit with Shoutlet and raised money there. It’s always easier if it’s your second or third time — if you’ve already had some successful exits. So I think that helped.
David had known me from that, and he kind of pushed me into into thinking about making a business with AirDeck. I even I even held back on him initially. I told him, “David, I, I don’t want to take your funding if I don’t know whether I can consistently convert them to paid users.”
At the time, I had about 300 free users. It wasn’t much, but it was enough to get product feedback. I asked him to give me 60 to 90 days to see if I can turn it from a freemium product to a free trial 14-day trial and convert some of them to paid users.
So I switched over the business model. And within the first few weeks, we started seeing a whole bunch of paid users signing up. And with that, I called David back and said, “Let’s do it!”
So Winnebago Seed Fund was our first investor, and they invested $500,000, which was enough for me to add to the team a little bit. And then we started getting some more momentum. And recently, we closed on an additional $3.4 million in funding.
Doris Nagel 15:39
I did know that, because the Principals at Rock River Capital, Andy Walker and Chris Eckstrom, were my guests on the show recently, and they actually mentioned your business.
And when they mentioned you, and I think he’s an upcoming guest! And lo and behold, here you are! It seems the world of Wisconsin startups – the ecosystem — is still relatively small, and people are pretty connected, which is really nice.
Talk a bit about your business model. You said you have paid subscribers. How did you decide what kind of model to use to monetize this?
Jason Weaver 16:23
That’s actually a great question. Prior to AirDeck, with my SAS companies that I’ve had before, I had always had an enterprise model — high contract value, at a price of $20,000+ for licenses. We had always gone after big companies.
But what I noticed during the few years that I had off after I sold Shoutlet, was that more and more software companies were moving to a subscription-based model. For example, Slack, and Zoom, and, GoToMeeting — they can sell down to the individual user, but they can also sell to large group of users on an enterprise basis.
If you think about Slack, you can buy a $20 per month license for one user and swipe your credit card, never talk to anybody, and just start using it happily ever after. But IBM also has 300,000 users using Slack — all the employees at IBM, and IBM pays a different price as an enterprise user.
So I knew that I had to the model differently this time. It was a real change for me to think about being able to sell down to a person that has a single presentation. But then I also had to be able to sell to the large enterprise.
There were some models out there, fortunately, that I could borrow from. Slack being one, Zoom being another. So we started price testing. We did a freemium model in the beginning that wasn’t converting enough people, so we soon moved to trial model. A 14-day free trial period seemed to be about the sweet spot, so that people can decide if they liked our platform or not.
We also started refining our features and messaging, and measuring our conversions. At the same time, as I watched how people were using our platform, it was interesting to see that the business started changing a little bit, too. I originally built AirDeck thinking it would be used mostly for sales pitch decks or investor pitch decks, because that’s the business I was in. But then I noticed about 30-40% of our users were trying to do voiceovers for full documents, like apartment leasing agreements, and sales contracts and those kind of things.
Doris Nagel 18:25
I would never have guessed you could use it for legal documents.
Jason Weaver 18:27
It was amazing to see. I log in every day and see something different that people are using AirDeck for. Walking people through different kinds of contracts or other documents. You realize there are some many situations where context is missing in a document unless it can be explained. Without AirDeck, you have two options: you can send it over and write a big old long email and hope they read it. Or you can get on a call with them, which also takes time and may be hard to set up.
Doris Nagel 18:51
Or you can fill it full of written comments, which I can tell you as a lawyer is VERY time-consuming, and costs the client a bunch of money.
Jason Weaver 18:59
Right. So as a lawyer, you know there’s a lot that can be left to interpretation if somebody isn’t there explaining it to you. So, the only other option is do it live. It’s very time-consuming just to walk somebody through something. Imagine going through a term sheet, where you have might have 100-page document, and you’re going back and forth, back and forth, explaining things.
With AirDeck, you could just voice over the document and highlight a point in paragraph two, section three, where we talk about, say, redemption rights, here’s what we’re talking about.
Imagine if you could do that in drop in all these different tasks and walk somebody through that document and send it over to them. They can watch it in their own time, which we call on- demand. I might create that document at five in the morning, you might watch it 11pm at night, and then you can reply back to me without us having that call.
If you think about the world that we’re in right now, everything is on demand. You have Spotify when you’re listening to music. You have Hulu when you’re watching TV or Netflix for movies, right?
Yet in the business world, everything is still live or static. Like an independent piece of paper kind of thing. AirDeck fills that on demand world: I’ll create it, I’ll add all the context to it with my voice, you watch it or listen to it when it’s convenient for you, and reply when you have time.
Doris Nagel 20:21
I mentioned my online training courses earlier. And I’m constantly listening to my daughter complain about her online Zoom classes. Both of which make me think there’s a market for AirDeck in educational online training, too.
Jason Weaver 20:44
Yes. I’ll tell you a little story about that. After I had the initial 300 AirDeck users, COVID broke out. In March of 2020. And I remember my daughter’s sixth grade science teacher coming to me and saying, “We’ve heard about AirDeck. We have 30 6th graders that have to hand in their final exam, and they need to be able to prepare it in their own time. Can we use AirDeck to do that?” And I thought that would be perfect.
So, I donated it to the class. And I had 30 6th grade students use it — without any training, by the way, that’s how easy it is. So without any training, they all created their final exams, and they submitted it to their teacher
Then, after that was successful, I was in contact with a group called Free educational resources. Somebody from amazon.com put this page together when all the teachers were in scramble mode. And I donated about 1000 licenses to schools — universities and schools throughout the world. And that really spiked our usage. So, we have universities down in New Zealand using it, and we have K through 12 schools in Ohio using it. The other day, I was listening to a student in China speaking Chinese finish finishing her final paper using AirDeck. It’s been wonderful to see how we could give during that period of time. It helps us for beta testing and awareness of our product, but also helps those educators worldwide.
Doris Nagel 22:20
How has COVID changed your business? Certainly, it’s been a terrible thing. But there are businesses that it’s helping. Is your business one of those?
Jason Weaver 22:40
It is helping us grow a lot. And I’m very blessed to have that happen. As I’ve told other people, this has happened twice in my life. The first time was when I started Shoutlet in 2008, when social media was really just starting to take off. And you might remember that time as a financial crisis and a housing meltdown. Everybody was pulling back on traditional advertising. Radio, print, and TV were getting killed. And I was really worried about that with Shoutlet.
But then all of a sudden, everybody wanted to be on Facebook, and my tool allowed them to do that. In retrospect we felt like, wow, that was perfect timing.
And same thing is happening with AirDeck. I certainly wasn’t expecting COVID to happen. I was thinking that people were still going to have in-person meetings, trade shows, etc. And now I think COVID has forever changed the way we communicate. Many more people are going to be working at home forever. Now I see companies every day announcing that their events are moving to virtual. And I think that will be for a while. Obviously, there are tools out there that you can use. Zoom is for live meetings, Airdeck is for on-demand. You need both. You need those kind of tools in your arsenal to be able to operate in business today.
So it’s really helped our business grow, creating awareness and showing people that by having AirDeck, they can add all that context to their presentations and documents, and really communicate better.
Doris Nagel 24:03
Jason, you’ve been through this before having started and successfully exited a couple of other businesses. What has been the best part about owning your own business? I guess you could talk about AirDeck or a couple of your other startup companies. But what is it that you love about starting up and running your own businesses?
Jason Weaver 25:12
I’ve always liked to be an inventor. For me, it’s less about being independent or a boss or something, for me owning my own business. It’s more about inventing products. You know, I consider myself a Chief Product officer first and a CEO second most of the time.
It’s funny, I was just having that conversation with my wife. I was in the kitchen the other day, and it just dawned on me: the coolest thing, I told her, about having this company is that I invented a product from nothing, zero, and people are using it, buying it every day. I just got cash from something I invented. And you know, I’ve done that three times, with different software that I invented. And whether it becomes a billion dollar success or not, just the fact that somebody finds value in it and uses it everyday for their business is awesome to me. It’s like writing a song and having people that love to listen to it.
So I like that the most. Being able to have a product that I can work on every day that I’m proud of. It really gives me pleasure to get feedback from customers, hearing how it’s changing the way that they run their companies. And that inspires me to go out and build other things. So that’s the biggest part: knowing that people appreciate something that you’ve built yourself.
Doris Nagel 26:39
When a business has been successful, like yours have been, is it hard to let go sometimes? I mean, an exit is the pot of gold at the end of the rainbow. But still, when it’s your baby, I imagine it must be hard to let go.
Jason Weaver 27:01
Oh, yeah. I cry every time. It’s just like the day your kids are born. And you know, I equate being an entrepreneur with having children. I have three actual children of my own. And with children, you can do the best to make sure that they’re happy. That they have what you think they need to succeed in life. But they’re their own person. Eventually, they’re going to grow up, go to college, get married, have their own career, etc. And all you can do is sit back and be proud of those things that you’ve contributed to their life.
The same goes for startups. I knew eventually that at Shoutlet, which grew to be a big company with lots of users, that it would become its own thing. And the hardest thing that I learned from that first company was that Jason does not equal Shoutlet. Jason is not AirDeck. AirDeck is something that I’ve created, but it will have a life on its own.
And I think when you can come to realize that, then you understand that, even though you can be emotionally connected these businesses, you have to let them grow up and grow beyond what you started.
Doris Nagel 28:08
I think you do if you want to scale. You might not want to if you want a lifestyle business, which is a perfectly OK decision.
But what I’m often struck by is the number of entrepreneurs who SAY they want to scale, and yet can’t let go of the things they need to let go of in order to actually scale their business.
To me, if you want to scale, you’ve got to have processes that are replicatable, so that other people can come in and do some of the things you & your senior team do, so that you’re no longer as essential to do those tasks. But I think that’s really hard for a lot of entrepreneurs. Do you agree?
Jason Weaver 28:52
Yes. There’s this quote from I think Ernest Hemingway that I use all the time when I’m with my employees: “Never confuse movement with action.” You can be busy, but just spinning your wheels and not going forward.
When I look back at the startups that I’ve consulted with over the years, it’s really been the vision to invent something and then the ability to execute on your vision. It sounds easy, but in fact it’s really hard. That’s even hard for me, even with a couple of successful exits.
I still have to hire people that fill in the gaps of things that I know I’m just not good at, to help me get that business to scale. And to put the pieces together that will help that business grow to where it needs to be. So a really big part of my learning experience has been to surround yourself with a team that can get things done with you.
Doris Nagel 29:49
Would you say that’s been one of the hardest things about having your own business?
Jason Weaver 29:54
For me, the hardest thing about having your own business is that it’s lonely at the top. You need to have peers that you can rely on, to comfort you, and to talk about different challenges that you might face.
I remember one of the most difficult patches at one of my former companies. I had to tell my employees where we were at financially, and that I didn’t know how we were going to make it through this quarter, but please stick with me — one of those kind of conversations. I had probably 100 plus employees at the time, and I noticed that none of them asked me at the time how I was feeling, or asked if I was doing all right. You know, everybody thinks the CEOs got the greatest job. It’s actually the most stressful job, right? It’s hard for me , too.
But I will never forget that when I came in the next day, I found somebody had left me a note on my desk. She wrote, “I believe in your dream.” I still have that note. It motivated me so much that I was practically in tears. I decided then that somehow we would live another day. And that kind of turned things around for me. So, you know, I think that they all got behind me, but it’s really lonely at the top. And it was comforting to know that somebody at that terrible time cared about how I was feeling as a CEO.
Doris Nagel 31:18
That’s sweet story. But you’re right – it’s tough. Guest after guest on the show has talked about the pressure of being responsible for employees, knowing that these families are depending on you for their livelihood and things like their kids’ education. So, it’s a lot of pressure. And that’s only one part of the challenge, right?
Jason Weaver 31:46
Yes, that puts the pressure in perspective. Not only do I have to make enough to take care of my family, but at the time there were about 120, people working at Shoutlet. And felt responsible for all of them. All of their families and other people that are dependent on them.
Many of them have gone on to do great things — become VPS and CEOs themselves. So that’s an awesome responsibility when you know you’re affecting people’s lives permanently with what they’re doing with you to build your company.
Doris Nagel 32:21
What are some of the roadblocks you’re faced with AirDeck, and how have you dealt with them?
Jason Weaver 32:31
We’re always dealing with roadblocks. I think probably the biggest thing that I’ve noticed is creating awareness. We have a really, really good chance thatf if somebody tries our product, they’re gonna buy our product. But the biggest challenge is they have to try our product, right? And you’re limited with the amount of marketing spend you have.
So we’re struggling with finding what channels are best. How do we get the most conversion, those kind of things. We still haven’t quite nailed that yet. But I think that if we can dial into that formula, then we’ll begin to scale just like my last company. When I raised 15 million for that company, I told people, that was my easiest round to raise, because I already knew how to scale the business — it was just putting in more fuel.
But for AirDeck, I’m still figuring that out. We still very much consider ourselves a startup, and we’re figuring out the things we need to overcome to be able to get ourselves to that kind of scale. So it’s a daily grind, and it’s hard.
Doris Nagel 33:41
I’m sure with your prior two businesses, they were more geared towards an enterprise. I’m sure that’s still a successful strategy for AirDeck to sell large groups of licenses, but I’m just thinking about how the ordinary person finds out about interesting and useful kinds of presentation software tools.
I’m thinking of things like VideoScribe, for example. They have a very loyal following, but I think struggle to get visibility. VideoSscribe, for those of you who don’t know, creates these little animated cartoons and lines drawings. People have probably seen them, but maybe didn’t know what it was.
Anyhow, I’m just thinking of how they market. I think I found it because I saw somebody else using it. And then I thought, “Oh, that’s really cool. I wonder how they did that?” And then I went and found it. But I’m not sure how you do mass marketing for that tool.
Jason Weaver 34:44
I think there’s two sides of that. You’re exactly right. If you go into a market that’s existing, you’re going to be fighting a lot of competitors. If you try to create a new market, then you have to create awareness, right? It’s like when the iPad first came out. Nobody knew they needed one until Steve Jobs told you did. You wouldn’t have gone searching for “iPad” because you didn’t know that it exists yet.
It’s the same for AirDeck. You’re probably not out searching, “How do I create narrated presentations and documents.” You’re probably searching for video, you’re searching for PowerPoint tools. And so we have to try to align ourselves with those businesses.
We are definitely a blue ocean. Meaning something completely different than what’s out there. And bringing something that’s brand new to market is always a challenge, to try to get that awareness out there.
Doris Nagel 35:33
I think selling into what I call a nascent need is one of the biggest challenges for a business. You want to be a disrupter, you want to be a unicorn, but be careful what you ask for, because it’s a very large challenge to convince people that you have a commodity they absolutely need, but they never knew they needed it.
Jason Weaver 35:56
I agree.
Doris Nagel 35:58
Where would you like your business to be in the next three to five years? What will it look like if you’re successful?
Jason Weaver 36:06
That’s funny, because we’re going through that planning process right now, for us.
We want to be synonymous with enterprise document engagement, meaning that anytime that you need to explain yourself on a document, your think immediately of AirDeck. So our goal is to be a household name like Zoom. You can’t get on a call now without everybody knowing what Zoom is.
I want that same level of awareness for us in three years from now. Where it’s like, oh, yeah, you got that legal agreement? Instead of doing a call, why don’t you just upload that to AirDeck, add your commentary and send it over to them. I want that to be the first thing people think right away, at the top of their mind. And we’re working hard with the partnerships that we’re putting together and different customers that we’re building relationships with to make that happen.
Doris Nagel 37:00
At some point, assuming this business is successful, you are probably going to let AirDeck go and leave the nest too, right?
Jason Weaver 37:14
This one is a little bit different for me.
When you when you look back at my history, there are some that had it took eight years for Shoutlet to go from zero to an exit, it took only 18 months from Spendship to go from zero to an exit. You know, sometimes you exit because you have to — you see changes in the marketplace. Or sometimes it’s because there are different things that you want to do with your life that don’t align with where the business is heading. Or you want to exit because you get a substantial offer, like we did,
And at that time, that was life changing money for me, right? That was that was that was going to help out my family and my friends and people that worked with me as well.
And then you get to the point where I’m at my life now, which is you want to leave a legacy. So for me, this one is not so much about the quick exit. It’s about making a global company. This one is about saying five years from now, when they look back, they think, “Oh, yeah, that’s the guy that started that AirDeck thing, right?
So, that’s what’s driving right now. I want I want to see this grow. I want to see it live on like we talked about with children. Right now, I don’t know if that’s a path to IPO or acquisition by a much bigger company. But I’m building this company to leave behind a legacy. That’s my objective.
Doris Nagel 38:41
You mentioned that you are an angel investor, and you’re an investor and advisor, you strike me as the kind of person who probably needs to have a number of different things going on to keep you stimulated and engaged. What other kinds of projects are you thinking about for the future?
Jason Weaver 39:08
I’m not in inventing or working on anything outside of AirDeck right now. All my passion is being poured into that, because I think it’s got a long way to go. There’s a whole bunch of things we want to do with it. We have some big plans for it. So, while I’m excited every time I think I want to invent something new or start a side project, I map myself back to AirDeck. I’m really pouring my passion into that.
But I satisfy that need to get involved with diverse things with a couple of consulting or advisory roles that my board and investors are aware of — things that I do to help other entrepreneurs. So, for example, I sit on a board of a really good emerging company called URL genius that does URL tracking and mapping, web to app downloads and things like that. They’re another Madison-based company funded by Rock River Capital. So, I can get involved in those as deep or as shallow as I want.
The thing I enjoy about that is, I’m a little bit older and further along than where those entrepreneurs are. I walk in there and as I told Brian, the CEO of URLgenius, it’s like reading my diary from Shoutlet. All the challenges that he’s having in trying to trying to grow a company, I’ve been through. It’s almost humorous. I’ll be like, “Oh, yeah, I remember when that happened. You know, we lost our biggest customer.” Or “Oh, yeah, I remember when that big competitor came in the market and we learned how to differentiate ourselves.” Or employee challenges, product direction challenges, those kind of things.
When you’ve had an eight year run in a startup with a good exit, you’ve seen a lot of things. And so that satisfies that need is getting those companies on path and sharing my experiences to hopefully help them grow their businesses as well.
Doris Nagel 41:09
If you come across somebody who’s like URL genius that actually has cookies that track podcast listens downloads, let me know, because I’ve been struggling with that. People often ask me, “Who’s your listenership?” And the only way to tell is anecdotally. I’m waiting for somebody to come up with a URL genius for podcasts. Maybe there is something, but at the moment, it seems like that’s a nut that hasn’t quite been cracked yet.
Jason Weaver 41:42
I’m not sure if that’s the capability of URLgenius – we’ll have to ask Brian or visit their website, but they have some very cool patented pieces of their platform that are really helping out some big companies like Louis Vuitton, and others that use it. I’d encourage you to check it out. They are definitely another local Midwest company that’s going to do very well.
Doris Nagel 42:04
Looking back at your journey and now being on your third time through, what advice would you give to entrepreneurs who are starting out?
Jason Weaver 42:21
How long is your show? Because there’s a lot!
Doris Nagel 42:27
Well, just the abbreviated version. I’ll have you come back for a longer version!
Jason Weaver 42:32
One is, only take funding if you absolutely need it. That sounds like a simple thing. But I see a lot of startups, particularly younger companies that are doing this for the first time. They build their product, and then immediately they think the next thing they need to do is go out there and get it funded. And when you get funded earlier and you’re not hitting your revenue tagets yet, you’re going get a lot more dilution than if you would have held on a little bit longer to get funding. So I always say, prove your product will sell first before you go get funding. Meaning, get your friends, families and contacts to actually purchase the product and show that kind of conversion. And then, when you feel comfortable that you’ve nailed that, then you can go get funding.
And not everybody’s money spends the same, you know. The partners that you bring in have to be true partners with you. When you receive venture capital funding, it’s like a marriage, as they say. So, I say prove that model first, before you go get funding.
The next thing I would say is to enjoy the ride. I remember one of my co founders, Aaron Everson, who is now CEO of another company, had just exited and sold his company Jellyfish to Microsoft for like $50 million. And I remember I didn’t have any personal net worth at the time.
He became the co founder at Shoutlet and we were working together. And all the times I was stressed out over that eight year period, he was always telling me, “You’re gonna miss this.” And I would be like, “Yeah, right, I’m gonna miss this. I want to exit and be done with the stress.” And he would say, “No, you’re really going to miss the startup world. You should be enjoying these moments, whether stressful or positive, as you go along.”
And the funny thing is, after I exited the company, it was the weirdest thing the next day –because I I chose to leave after the exit. Nobody called me anymore. There were no more emails. No more meetings that I had to be in. I was just off work, you know? And that was weird, and he was right.
So the next thing you do as an entrepreneur, even if you have a good exit is you’re like, I’ve got to get back in the game. If I’m sitting here just idling, I’m just gonna wither away. So you can work on your next idea, but for me, if I’d been able to enjoy the journey a little bit more along the way, I would have had, a more substantial, fulfilling feeling when we had our exit. So now I’m kind of stopping and smelling the roses every single time we have a tiny victory. It’s definitely celebrated here at AirDeck.
Doris Nagel 45:08
So thinking about where would I go next? What’s my plan B, what’s next for me, and being prepared for that sounds like a related piece of advice.
Jason Weaver 45:37
Yes, exactly. So, thinking about the next thing, but also just really enjoying the steps along the way. I’m still learning that, Doris, to be honest with you. I’m learning to slow down a little bit and and really see the bigger picture, rather than just focusing on my tasks for the day.
Doris Nagel 46:03
How can people reach you if they’re interested in in chatting with you about any of the things we’ve talked about today?
Jason Weaver 46:27
I encourage everybody to have a free trial of AirDeck. You can sign up today at airdeck.co. And I love hearing from people. For me most effective communication platform right now is LinkedIn, where you can find me easily — I’m very visible there. We also have a great company page on LinkedIn, and you can reach out to me that way as well. I’d be happy to connect with anybody.
Doris Nagel 46:55
Jason, thank you so much for being on the show today. It was really a delight having you.
Jason Weaver 47:01
I’ve enjoyed it. Thank you for having me.
Doris Nagel 47:03
We have just enough time left this week to talk about a question from Barbara in Indianapolis. She says she’s realized she needs more help with sales for her startup business. She asked whether it’s better to hire someone as her first actual employee, or to try to find someone on contract.
Barbara, great question! It’s certainly one that many small businesses getting started wrestle with. The right answer, of course, varies depending on your situation. But here are some things to at least consider.
First, it’s tempting to hire that first employee. You’ll feel like a real company. Also, if you hire someone, you may feel like you have more control over this individual, that they’re a more permanent part of the team and for sure dedicating 100% of their time to your sales.
But there are some downsides. First, there are a lot of expenses associated with hiring, especially that first employee. You need to put in place a number of things that will scale as you add employees. But for that first employee, there’s a lot to do. You’ll need to set up a payroll vendor, you’ll have to have someone to ensure that all the appropriate taxes are withheld and paid.
You’ll need to think about benefits. Should the salesperson have a car or car allowance, or health insurance? Will they get vacation or sick days? Will they get stock shares or stock options?
The taxes are not optional, but you can choose not to provide a lot of these benefits. But if you don’t provide them, the individual might be willing to make some compromise for longer term gain, especially if they believe in what you and the company are doing. But if they’re talented, they’ll have other options. And the benefits that other companies may be offering to those talented people may be more attractive to some.
A lot of companies are really watching their pennies and want to go cheap. But if this person is the right hire, they can make or break your company. Speaking of that, there’s still other considerations. What if the person doesn’t work out? In my experience, many companies who hire their first employee find out that there were skills, traits, responsibilities, etc that really were needed that they didn’t realize. Things that you want and need this person to have, and if they don’t, they aren’t a good fit. And so you may have to go through the trouble and the anguish of letting the person go and starting all over with the hiring process, all of which can really set you back financially, as well as being a real time stuck.
Hiring an employee may also limit your flexibility. Sometimes you need help, but may not yet need a full time person. And you might not know that when you start off. So what if you only need .6 of a person, but you’ve agreed to pay for a full person? On the flip side, maybe you could could definitely use a full person, but your cash flow projections were a little optimistic, and you can only afford to pay point six of a person. But an employee who is full time is entitled to receive their full salary every single month. You might be able to negotiate a bit with them, but you are taking on risk because unhappy employees can file complaints.
There are also administrative responsibilities when you have an actual employee. There are quite a number of statutory requirements, like an employee handbook, and things like workers comp. Again, they can all be outsourced, but they add to the cost. So the reality is that hiring that first employee adds a lot of expensive administrative burden.
Because of this, many companies that are starting out “hire”somebody on contract. Some refer to these people as employees, but technically, they are self employed, and you report the money you pay them not on a W2, but on something called a 1099 form. If chosen and compensated well, these individuals can provide the same results with a lot more flexibility and less administrative burden. But here again, you need to be very careful.
I would recommend taking a listen to a previous show with John Sartoris, where we focus specifically on some of the pitfalls with contractors, or 1099s. The IRS has a somewhat different view about who’s a contractor and who’s an employee than a lot of employers have. The IRS says that if you treat people like employees, they are entitled to claim they were actually employees, and were either wrongfully terminated, or were in are entitled to Social Security withholding and other benefits that they didn’t get. And that can be quite costly. A lot of employers love 1099s, because they can plug and play. And actually a lot of the 1099s like it as well, because it gives them flexibility, too.
But the IRS believes that contractors should only be used for specific projects, not as plug and play people who in their view are essentially filling the role of employees. Sales in particular, I think is a risky area. It’s one thing to contract with an accountant for a few hours of bookkeeping and data entry or to do taxes, or to hire somebody who does your social media, or a webmaster who does a few hours of support here and there. Those are administrative functions, and those people are generally in the business of providing those kind of services to a variety of companies, and you’re just one of them. Providing services like that to various companies IS their business. And therefore, it’s hard for them to argue they’re an employee of your company when they’re doing the same thing for other businesses.
But sales is generally not an administrative function — it’s quite integral to the success of a business. It’s also not generally something that you need for just two to three hours a month. Hiring a 1099 sales person is quite risky, in my opinion. Issues tend to crop up when people feel like they’re being treated unfairly or most often when they are terminated. It can even occur if the person goes to file for unemployment and the authorities start asking questions.
I had a client recently with a 1099 salesperson and when that person was terminated, the person sued and claimed he was actually an employee under the law and was wrongfully terminated. They ended up settling, but they settled because my client was significantly at risk with the IRS and other authorities. So it’s really important if you hire a 1099 that to make sure this person has other clients.
Another option that sometimes is available — not always, depending on the industry or your location — is to hire a company that provides contract sales. There are companies out there whose business is to provide sales, either full time or part time full time. If you are able to find this option, think about whether they dedicating specific individuals to your business, so that you’re not training all sorts of different people and having them turn over. And of course, you really want to think through the performance metrics.
So, Barbara, I know that doesn’t answer your question because there’s a lot I don’t know about your situation, but I hope it does give you and maybe some of my other listeners some things to think through and some angles to consider. If you email me back, I’m happy to help you delve into this in more detail to come up with the right answer for your business.
That’s our show for this week. Thanks so much for listening. And thanks again, especially to our guest this week, Jason Weaver, the founder and CEO of AirDesk.
You can find more helpful information and resources on my website globalocityservices.com. There’s a library there of free blogs, tools, podcasts and other resources.
My doors always open for comments, questions, suggestions, or just to shoot the breeze. You can email me at dnagel@ lakesradio.org — I promise you’ll hear back from me.
Be sure to join me again next Saturday 11am Central noon Eastern.
But until then, I’m Doris Nagel, wishing you happy entrepreneuring!
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