How to Growth Hack Start-Up Investing
Tatyana Gray interviews Ivan Raiklin
Hey, everybody, welcome back. I’m beyond excited to bring my friend, a brother from another mother, Ivan Raiklin, to you today. Ivan is a fellow recovering attorney, a green beret-turned-start-up advisor and investor. Ivan is a huge growth hacker and is going to share his unconventional methods of getting involved or growth hacking his way into start-up investing.
Last, but not least, Ivan is a fellow Russian-American, and I have to tell you, I’m usually not a big fan of Russian, former Soviet guys. There’s just something that the Soviet culture did to so many men there to turn them soft and turn them into drunks, basically. It’s a huge problem in most countries of the Soviet Union, but there are a few outliers. Guys with Russian or Soviet heritage, they are bold, driven, hyper-ambitious and really stand for everything good that this country has to offer. Ivan is one of these guys. On a side note, I’m also a fan of Gary Vaynerchuk as well and, mark my word, in a few years, Ivan is going to be just as big as Gary V.
Ivan, welcome to the show. Tell us, how did you get started with angel investing?
Well, let me bring you back to a little story that was probably around spring of last year. I had the idea of transitioning from the government military space that I had been involved in and wanted to learn about. I wanted to find something that I was passionate about and I’m usually passionate about technology and what’s new, cutting-edge, bleeding edge — as some people call it — and I wanted to learn about the sharing economy in the sense that I wanted to see both sides of the platform. As you know, marketplaces that are out there like Airbnb, Uber.
So I started on boarding from both sides, I guess if you will, renting as well as renting out, or driving out as well as being a passenger. This was to get a sense of what the algorithm was that was being used on platforms such as Uber, Lyft, Sidecar, and then also using it as a tool to network. I was still maintaining a full-time job, and I found that in the after hours, I was able to network — now that I was back in D.C. — as well as learn about the different platforms. On one of the trips that I was on in Sidecar, there was an individual that came and I asked him, “What do you?” and then they explained it. They’re a brand marketing director for a company called Piazza, a start-up. I was trying to get into the start-up community here in D.C. because I’d just gotten back the previous fall.
So I learned a little bit about start-up and I said, “You know what, that’s interesting. If you can set up a meeting with the CEO, that would be great,” so one thing led to another and I basically started talking with him and a couple other start-ups and I said, “I want to start investing in your company,” and that was, essentially, my first deal that I did. I found him through, essentially, a ride-share platform while I was doing market research in the sharing economy. So, very anomalous, and I’m proud to actually explain that story. It sounds like a very different deal flow mechanism but it is a way that you can network and communicate with people.
I was going to say it is very different. I have not heard of anybody really trying to do that. You’re interested in sharing economies so you can explore both sides of it. You’ll be a landlord and you’ll use Airbnb as a services or you want to learn more about Uber or Lyft, so you’ll do both sides of it. I think that’s a pretty unique way to get familiar with things.
Right, so after, say, about two months of doing that, I felt as though I was pretty much an expert on a lot of these different platforms. I looked at all the different blogs that were out there and the main blogger out there — his name is Harry Campbell — who was on one of my Blab shows that I have on the sharing economy and it seemed as though he was blogging about things that I pretty much already knew myself. I had already done that, so then I started to contribute some insights to him and I thought: ‘why not also start creating content?’ But that’s another story.
Going back to the angel investing piece: my first deal was with Piazza and I wrote a check — very scary — but I thought, ‘In order to become an angel investor, you’ve got to write a check.’ So I wrote the check and it was scary, like you mentioned in previous episodes, but I talked it over with my wife and she said, “Alright, let’s do it.” At the end of day, if it doesn’t work out, just by virtue of doing it, I feel as though what I’ve gained from it, even if I do lose the entire investment, I think the tuition in and of itself is worth it and I think, moving forward, it’s prepared me.
So I’m actually getting ready to do a second deal with another company called The Intelligence Community. They are literally an Upwork for the national security space. So, freelancers connect in order to support government contracts as well as defense sector contracts. They just recently did a launch in October and I was on the second call with them last night to discuss our way and, hopefully, in the next week or two, we can finalize the arrangement.
That sounds cool. I recently met an amazing woman here in Sun Valley that relocated here, she runs a non-profit called American Women Veterans. She’s coming out of the intelligence world and trying to do more civilian things but I’ll have to tell her about this start-up you’re talking about.
Yeah, it’s a definitely interesting start-up. They’re going to be at launch festival next March. Hopefully, they’ll proceed on and get some notoriety but we’ll see. They have a significant player on their board of directors. It’s the former director of the Defense Intelligence Agency. So there’s some significant network effect there. Also, once they tap into the intellectual capital of the Silicon Valley area, I think it should be a successful start-up. What CEO Graham brings to the table is the understanding of the federal government and contracting system because, even though you have these freelance marketplaces like Upwork, they don’t understand how to deal with the government and that’s a big pain point that hasn’t been addressed yet. They may even be ahead of their time even though these freelance marketplaces are already out there. It’s just that the government is, a lot of times, slow to adopt. But I didn’t want this to be an episode to be specifically about those company and my portfolio. Small, which it is.
No problem. I love learning about cool start-ups, but thank you for sharing about sharing economy. We’ll talk more about that. But I also know that you and I also share an interest in legal tech. So, can you tell us a little bit more about your interest in legal tech start-ups?
Sure. The two companies I mentioned, obviously, are in the sharing economy space and the legal tech space. Part of my deal flow is I host four shows on Blab every week and one of them is Startup Mastermind, another one is DC TECH, another one is Sharing Economy, and the last one is Legal Tech. What I like to do is identify folks and brand new company start-ups that I would like to find out more about, bring them on the show as, essentially, the first discussion with them, and also create content out of it.
In regards to Legal Tech, I have a show on Thursday evenings, and we talk about legal tech issues. Now, I haven’t invested and I found one company. Essentially, it was using artificial intelligence to curate large amounts of documents by using computer AI to curate it and then churn out a short version summary of what those reams of documents consisted of. It’s your first cursory assessment of all the evidence or documents that were in there and I had them on show.
So, I used that platform to identify different companies that we could potentially invest in and. This year, I really want to focus on the different companies that are involved in this sharing economy as it applies to legal profession, like your on demand legal services. There’s probably 12 or 13 that I’ve identified so far and it seems as though one of the ladies that you connected me to last week, who is the CEO of Traklight, who is hopefully going to talk about that on Thursday on our Blab show in the evening. She’s set up to be there and you’re more than welcome to join in any time because it seems as though a lot of angel investors, at least in our circles, are recovering attorneys.
Yes. You are having the Blab with Mary from Traklight? So, I would encourage all the viewers t tune in. In Blab, you can actually replay and that’s what I’ve been doing because the live shows are a little bit hard for me because it’s in the middle of my son’s bedtime.
Ivan has regularly scheduled Blabs and I think all the time, it’s around 9pm Eastern Time, which is 7pm my time, so it’s really hard for me to catch them live. I’ll try this coming Thursday, I think. But anyone can check out all the replays or quite a few of the replays on Blab. I’m looking forward to jumping on live some time.
I apologize because I have kids too and that’s why I do it at 9. I tuck them in and then immediately press record.
You’ve just got to figure into your routine, what works. With kids, it makes it definitely a little bit harder. I think what you probably have found with your networking is that there are so many people our age, 30s, early 40s, that are able to be angel investors or that satisfy their creditor investor standard but, for whatever reason, they’re not investing in start-ups. So I really hope to reach out these people. Many of them do have kids so I guess we’re all on the same boat on this.
Right, and I like what you mentioned. I think it was back in episode 7 when you were talking to Nick about how 93-97% of those that can be accredited investors don’t invest and are not angel investors. So, there’s a huge opportunity there, obviously. A lot of folks even have a full-time job and I still maintain a full-time job. If you’re just doing 40-50 hours a week, there’s still wiggle room there to play around and create sufficient deal flow. I think I’m going to pre-empt your question of a tool that I use and I think every single person on every single episode always says AngelList.
Yes.
So, that’s one of the tools. But there are other platforms out there like Circle Up , who I’m sure you’re familiar with.
Yes.
That’s definitely a good platform. It’s more in the consumer space . There are a couple of companies out there that are tech-related that have identified that I’m tracking right now to see where they go. They’re interesting in the wearable space, like consumer wearable, which I think is a very interesting vertical.
I invested in a platform that’s related to healthcare. It’s called Healthfundr. It’s a similar equity crowdfunding platform for anybody interested in healthcare investing.
Going back to your point for almost 9 million people out there that can be angel investors and, for whatever reason, they’re not. You can do angel investing in a pretty active way. I’ve taken a pretty active approach to it and, basically, I don’t do it full-time but probably over 20 hours a week I dedicate to angel investing. But you can still have a full-time job and take a little bit of a passive approach and use syndicates or organized angel groups. A lot of the work is either shared or even outsourced like you do with the syndicate.
Absolutely. You actually made me think of a story. Reviewing 2015 for me, some of the events that I went to in order to identify and curate different companies that were out there to at least know the spaces or verticals that I wanted to get into, I went to the pitch competition finals for 1776, which is an incubator here in D.C. I also did the New York Tech Day, Chicago Tech week, LAUNCH. All the while, I’m actually doing this while I’m on vacation. So, yes, I have a full-time job but I’m taking some of my vacation time — because I have a lot of it — to actually travel. If some of these events are on the weekend, all the better, then I don’t have to take vacation times.
So, you have to balance out a little bit of family, a little bit of your passions, and a little bit of taking away time off work to do those things. I guess most people don’t want to do that but, like somebody mentioned before, if you want to be an anomaly and successful, you’ve got to act a little bit like an anomaly. If you’re acting like everybody else, you’re not going to set yourself apart and be successful in any endeavor.
I totally agree and, nowadays, it seems like so many employers are willing to work with people on flexible schedules and so that makes it easier for people to attend events like that. I know we’ve talked before about the events and you were asking me if I’m coming to this event or that event and I think events are a great way to kind of get to know and to network.
Yes, because, essentially, you initiate contact and then I bring them on the show and then it creates that funnel for deal flow.
It does, yeah.
But if you can’t travel, AngelList is definitely the platform. Get with syndicates — I think you’ve already beat that down with the other guests so I won’t really talk about that. Oh, I’ve got to give a shout-out. Last night, I got an email from — I think you know who I’m referring to — Rob Ness. He’s an angel investor. He’s based out of D.C.,and we’ve become friends at this point . Yesterday, he was a top trending syndicate on AngelList.
That’s nice. That’s cool.
So, he’s definitely hustling his way into creating his syndicate and he just posted his first deal last night.
Yes, I see it.
But right now he’s number two because fast ventures…
Beat him?
Yeah, I mean, it’s a VC, not an individual. So he’s been by coastal last few months between San Francisco and D.C. and he’s actually in a similar boat as myself where he has a day job and he’s doing this in his free time.
That’s awesome and if you heard on some of the episodes, my long-term dream is to be able to launch a syndicate of my own. It’s nice to see that here’s an individual, not a VC firm, that he’s able to do so well. So that gives me hope.
And he was able to convince and cajole Jason Calacanis to be one of his investors.
Oh, nice.
Obviously one of the biggest names in the community. Rob, he’s my mentor.
But wait…there’s more!
This post has been adapted from the Angel Investing with Tatyana Gray podcast.Listen to this recent episode for more great information from IVAN RAIKLIN!
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About Tatyana
When Tatyana learned that out of almost 9 million accredited investors in the United states only 300,000 (about 3%) were active angel investors, she made it her mission to attract, educate, and inspire the next wave of angel investors in this country.
As a new angel investor herself, Tatyana loves to learn the craft of investing in startups from experienced angel investors. It was only natural to share this process with a broader audience via her Angel Investing podcast.
Follow Tatyana on Twitter at @tatgrayid. We welcome your comments.
