SaaS Interviews with CEOs, Startups, Founders
He hated his remote guitar lessons then spent $8m on new SaaS MVP, 5 patents later he's preparing for launch.
07 Jun 2022
Chapter 1: What is the main topic discussed in this episode?
How am I in the beta today and what are you watching for? Yeah, this is exactly the goal is to accelerate your learning velocity. It's the most important thing when you run a startup is learning quickly and adopting the product based on what you see. You are listening to Conversations with Nathan Latka, where I sit down and interview the top SaaS founders, like Eric Wan from Zoom.
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Hey folks, my guest today is Amir Ashkenazi. He's the founder and CEO of Switchboard, his first remote-only company, and he's never going back, he says. He's a six-time entrepreneur that pioneered comparison shopping, shopping.com IPO, which has been acquired by eBay, programmatic advertising, that was adapt.tv, which was acquired by AOL, and AI assistance for meetings.
This is Toki, which was acquired by LogMeIn. Amir, you ready to take us to the top? You ready to go? Ready to go. Let's go. All right. All right. So you've had some success here. Just to be clear, those three companies I just mentioned, you founded all those, correct? Yep. Yep. So look, I'm just going to say this bluntly. You're like a super rich guy. You can do anything you want.
Why get into remote cloud co-working? I insist on doing what I love. And what I love is building products that are absolutely innovative that you don't have right now and that you really need. So how would you describe this? It's sort of a blend between what and what. Yeah, so Switchboard is a cloud co-working space. It's the next generation collaboration platform.
It really allows people to do things together as if they were sitting side by side. When you think about the way we collaborate right now, mostly through video conferencing, it's not very collaborative. Like we can see and hear each other, maybe show a screen. But when we actually want to do things together, it seems to fall short. Yeah.
And there, what's interesting is like, you know, we just had Zeb Evans on, we had Eric Wan on before Zoom IPO. So we've talked to a bunch of folks and like, you know, Zoom just released a whiteboard and ClickUp's trying to do this. And like everyone sort of has their own version of this. And I just look at all of them and I go, who's going to win this space?
Is it really going to be a technical breakthrough or it's going to be who dominates distribution or something else? What's your take? So let's focus for a second on the technical breakthrough. So what we did is we developed cloud browsers.
Those are essential elements that allow you to bring any tool that you already use, things like Google Docs and Figma and Trello and Jira, and they become immediately collaborative. Even the regular website become immediately collaborative in this switchboard workspace.
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Chapter 2: Why did the guest transition from guitar lessons to a remote cloud co-working platform?
So tell me, just you have to forgive my naivete here. What makes this a hard technical challenge? Why can you solve it and no one else can or very few other people can? Well, browsers were built as single player applications. They were basically built for one user to interact with the web. They were not built as collaborative applications. And basically what we did is turn them to exactly that.
So they run in the cloud. You don't need to share your screen. They keep memory of your room. So when you open a room in Switchboard, it starts exactly where you left it last time. You don't have to prepare for it. You don't need to summarize it because it's all in the room.
And the difficult part is mainly around security, scalability, and the UX of how do you manage multiple applications within one browser. Switchboard does not require you to download anything. or learn any new tools. Everything works in the browsers with the tools you already use. Very interesting. Okay, so put this on a roadmap for us here.
When did you write the first line of code for this platform? So we really started two years ago. It's very funny. I'm a guitar player, not very talented, but really enjoy that. So with my guitar lessons moved to online, it was really terrible. So you need tools like a metronome, you need notes, you need multiple videos. And all I got is the instructor's face.
So that was the moment I said, okay, we need something else here. So that one we started, it was May of 2020. Quickly in June, we started to write code for this. I think it took us six months to understand that this is actually not for guitar lessons, but this is the core problem that every remote and hybrid team is facing. Mm-hmm, mm-hmm. And this makes a lot of sense.
Now, were you scrappy at the beginning of this? Did you want a lot of second time, third time, fourth time founders to go, you know what? I hated working with a co-founder the first time. I'm going to own it all at the beginning. Just pay everyone a lot of money. What route are you taking here? This is your fourth or fifth venture. Actually, your seventh, eighth venture. Six. It's only six. Six.
Okay. Yeah. It's all about partnerships. It's all about getting people that will join your journey and that are excited about it and can contribute to it. So very quickly... We partnered with the right VCs to accelerate our path and with the right first employees to build this thing. I don't believe that you can do great things alone in a room closed.
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Chapter 3: How does Switchboard enhance collaboration compared to traditional tools?
It's all about creating this human connection and inspire people to go in a direction and believe that this is the future. But you're burying the punchline here, which is when my research team researches the company and prep for this interview, you're the only one listed as the founder. So you were day one guy. There's no co-founder.
I am a single founder, but I view my leadership team as absolutely essential for this. And they are partners to every decision that we made along the way. Who was your first partner in building this? So who was my first partner? So my first partner is actually Daniel Portoio. Daniel Portoio was the head of talent in Greylock, and I knew him for many years.
And every time I met him, he gave me the right connections and contacts and introductions. And when I read that he's starting Sweat Equity Ventures, now it's called the General Partnership, I immediately called him and said, let's work on this together. It was transformational. It quickly connected me with the right recruiters and advisors and so on. So we got it off the ground very quickly.
It still took two full years of development in stealth mode to reach the point we're in right now. So Amir, come on. I want to know how painful this was. If you had to quantify how much money you spent just on development before you shipped the beta and did a product launch, can you quantify that? Are we talking like a million, two million, five million to build it? About eight.
Oh my gosh, 8 million. Interesting. I would have never guessed that much. So what am I missing? What makes it so expensive? What you're missing is that from a technical perspective, this is a really difficult problem to solve. And I'll give you an example. So in two years, we already have five granted patents for the work that we do. Oh, wow. It never happened to me.
It usually takes five, six years. And the reason is that this is really difficult and really no one has done it to the level that we're doing it before. So, yes, it took a lot of work and some money, too. Five patents. Have you defended any of those patents? Yeah, all of those are granted and there are more in the pipeline.
But have you had to defend any of them or have you protected any of those? Not yet. No one is doing it right now. So probably in the future. Very interesting. Okay. And it's interesting you mentioned Daniel. Now, he was at Greylock. Now, did you already generate a big return from Greylock from any of your prior companies?
No, Greylock never had any investment or interest in any of my past companies. It was just pure friendship. With Daniel. Interesting. So is he full-time at the business? Well, he's not full-time because he's running the general partnership, right? He is a partner at the general partnership. Yeah.
So who, I guess, sorry, what I meant to ask was who was your first-time partner in terms of full-time employee? Yeah, so I obviously called some of the people that I knew and worked closely in the past with, just name one, because everybody's contribution is so important here. But what I can tell you is that by adopting 100% remote work structure, it really opened a world of opportunity for us.
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Chapter 4: What technical challenges does the guest face in developing Switchboard?
Well, Remote has delivered. Sign up today and receive a 50% discount off your first employee for the first three months. Check out nathanlatka.com forward slash remote and enter promo code LATKA to get started. That's nathanlatka.com forward slash remote and promo code L-A-T-K-A. Check it out today before you miss out. You were recruiting, though, top tier talent, right?
Chris Jones, you know, he had time at Databricks. He had, you know, as an advisor to companies that we know very well, you know, Little Bear Labs, Dynaboard, others. You sort of lull, it looks like you sort of lull him in an advisor role. And then before you know it, he's joining full time. Is this like the Amir playbook? Should we all copy this? Yeah. Absolutely.
You should copy, always partner with the best people you can find. And what I found is that the best people are really not looking for just compensation. Of course, you have to be competitive on compensation, but it's really about the journey and about the mission. They get excited about this. And the best thing as a startup CEO that you can give these people is a front seat opportunity.
in this journey. Just completely expose them to everything that is happening. Don't shield them, not from the bad days and not from the good days. Just have them as complete partners to the journey. That's a super interesting take. Okay. Now, just to be clear, again, pre-revenue today, right? Still building out the beta program. What are you learning?
I mean, imagine a guy like you, you're doing a beta so you can accelerate your learning velocity. So how am I in the beta today? And what are you watching for? Yeah, this is exactly the goal is to accelerate your learning velocity. It's the most important thing when you run a startup is learning quickly and adapting the product based on what you see.
So the first thing that you learn is like, who is it? Who are the personas? Who is even your target customers? And whatever you think, you'll always learn something new. So, for example, we knew that this is great for startup CEOs. We knew that this is great for design and product managers, but we did not anticipate how many people from higher education are actually going to use that.
So this is one thing that we've learned. It's very important to stay very close to the users that are using it. Another thing that you learn is about the retention and the virality and usage patterns of the product. And for a product like ours, obviously, the virality is critical. The main thing that people do or the first thing that people do on the product is inviting other people.
You want to encourage it. Our marketing is based on that. Okay, so I want to go deep here for a second. What tools are you using to measure when key retention, like activation, usage things are hit in the app in the first sort of seven days? You use like Pendo or something else? Break down that tech stack for me.
Yeah, so obviously we monitor everything and we use Snowflake and Amplitude and Datadog as like the main tool to monitor everything that is going on in the platform. The key is not so much to collect the data, but actually to spend the time analyzing the data and gain real insights from it. And what are you seeing right now? I mean, have you been able to nail down to a viral coefficient?
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Chapter 5: How did the guest's experience shape the development of Switchboard?
It's audio and video. They'll be able to see it. I didn't know that. Okay, you should have worked on my background too. No, it's a great background. It's a great background. Okay. Last question here before we wrap up. I wouldn't expect a first-time entrepreneur to be able to go out and do what you did, which is launch a beta, pre-revenue, and raise $13.8 million.
So there's something to be said for Amir's life as a founder. When you look back at just your history over the past 10, 20, 30 years, what were some of the early things you did in your startup life that you think worked really well now 10, 20 years later? So I think it's absolutely critical to raise money from external investors, even if you can fund it or you think that you can fund it.
Your ability to raise money is the number one thing that will determine your future success. And I use every round as a way to validate our assumptions and to check the strategy. And If you cannot raise money, then you need to go back to the whiteboard and ask yourself why before investing more of your personal money on this. So this is something that guides me along the way.
The VCs are not only funding the company, they're important partners to building it. Is there anything, you know, a lot of, a lot of second time, third time founders will tell me, Nathan, I wish I just sold my first company faster to get an exit under my belt to just learn, even though it wasn't, I wasn't, didn't get the best price possible.
Are there any lessons like that you wish you did earlier on or no? No, look in total, I sold three companies. And in general, I, um, regret not holding each one of them a bit longer. We had the shopping.com that was a pioneer in e-commerce, a pioneer in comparison shopping. What did eBay pay for that in 2006? $630-something million. And how much had you guys raised?
It was a little bit difficult to calculate because there was deal time that raised money. And then we acquired a company called Opinions and another company called better, even better. So I can do the math. I see. I see. And what about ADAPT? Did you bootstrap that one or no? No. ADAPT TV also raised money.
I think it totally raised $48 million and that was acquired by AOL for about $400 and something million. Sounds like a great, unless I'm missing, unless it's a 3000 year earn out for 99% of the deal. It sounds like a pretty good exit. And then fast forward to Toki. Did you bootstrap that one or no?
Uh, that one, it actually, we add in the first, um, uh, one in one day, we had a term sheet from a VC and a proposal to buy the company. So we actually, the plan was to get VC money, but we got the card so quickly that we didn't have enough. I was going to say that was a nine months. Your other twos were five, six, seven years. That one was nine months. So interesting story. All right.
When can you share, are you open to sharing how many folks are in the beta today? Are you keeping that private? We're obviously keeping that private, you know that. I don't know. We get a lot of people share beta numbers. We get a lot of people share that. I guess what will make you come out of beta? Are you trying to hit a million users or like what's the thing?
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Chapter 6: What strategies does the guest use to recruit top talent for their startup?
We already have a community of really passionate users. We're looking to grow this a little bit before we get into monetization and scaling customer acquisition. All right, Amir. Let's wrap up here with the famous five. Number one, last book that you read. Last book that I read, I'm really ashamed to admit it, but it's very tactical. It's called The Mom Test. It's how to do user interviews.
It's very tactical, but it's very good. It will teach you how to get the truth from anyone you speak with about your product. You said the monk, like priest, right? The mom test. It's called The Mom Test. Oh, mom. Because even your mom will not be able to lie to you. Ah, I love that. Okay, The Mom Test. Number two, is there a CEO you're following or studying? Oh, there's so many. There's so many.
The best CEO I've seen was actually my co-founder for shopping.com. His name is Nahum Sharfman. He's unfortunately not with us anymore, but he's still with me. And I think about him every day when I make decisions. Number three, what's your favorite online tool besides your own for building switchboard?
Yeah, I really like Loom, one, because the CEO is an investor in Switchboard, but two, because it's a fantastic tool for asynchronous collaboration. Number four, how many hours of sleep do you get every night? I'm not a big sleeper. I think it's important to sleep well. I would say six to seven is probably my number, yeah. Fair. And what's your situation? I mean, you're married, single kids?
Married, three kids. Oh, wow. And how old are you? I'm 51 and a half. 51 and a half. Very cool. Last question. Something you wish you knew pre-shopping.com days when you were 20. Oh, so many things. In general, I think that we were fortunate to see the internet evolve in such a dramatic way.
And we were excited about this in the beginning, but probably did not see 1% of the overall directions that the internet is going to take. So, I wish I could have seen more, but I'm just grateful to be part of this journey and experiencing it firsthand. Guys, switchboard.app. When you visit the website, you go, this looks very simple.
And then you listen to this interview and go, oh, he has five patents and spent 8 million bucks on the MVP. There's something very special here. They're still in beta tracking usage metrics. He calls them the love metrics, as we all do. We'll see what happens, though. Hopefully coming out of beta soon, so more folks can use it. Successful six-time entrepreneur, so he knows what he's doing.
Reading the mom test to do better user interviews. Amir, thanks for taking us to the top. Thank you so much. It was a lot of fun.
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