GE Ep 60: Ian White, CTO & Co-Founder of Sailthru on Hiring Technical Talent

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Ian White, CTO & Co-Founder of Sailthru on Hiring Technical TalentIn today’s interview we’re talking to Ian White who is the CTO and Co-Founder of Sailthru, an online personalization technology he and his team had to bootstrap for two years while no one believed in it. Now they’re doing low seven-figure business deals and seeing much more success. Today, Ian will talk about the importance of hiring technical talent, adjusting to changes, and what you should do when a member of your team is no longer a good fit.

Keypoint Takeaways: Running with a good idea & starting a company at the worst possible time

After explaining how he met Neil Capel who would eventually become a fellow founder and CEO of Sailthru, Ian gets to the point of where they discovered the online personalization needs through the problems they faced with the various companies they worked for.

Recollecting their thought process at the time, Ian said, “What if we had a technology that could truly personalize one-to-one communications on an individual basis? What if we could do that, not just in email, but we could pull together a user’s data from on-site, their whole click stream activity? … If we could pull all of this together and form a unified picture of each individual, then the way you communicate with those people could be totally personalized and individualized.”

They figured out how to start doing it and got to work launching their company in September 2008: in the exact same week that Lehman Brothers crashed and the country was in an economic depression.

They had to bootstrap for two years until they raised their first round of funding in June 2010, and since then have grown to 170 employees with offices in New York City, San Francisco, Los Angeles, and London.

A growing company means changing dynamics

“Growth, technology: these things inherently mean change,” says Ian. “And one of the things you just have to do is keep being responsive to change.”

In the beginning, when a team grows by as little as 10 people, there needs to be a fundamental difference in how the company works because more people means you need more process and more structure. A 3-person company made up of just the founders is vastly different from a 25-person company.

As your company scales, it’s important that you don’t get too attached to one way of working or one idea you want to work on. If things don’t work, then Ian’s advice is to “Kill ’em quick and double down on the ideas that do work, and try to be data-driven about these types of decisions.”

When one team member’s role is no longer a good fit for the company

At the end of the day, you have to make the right decision for your business. But having tough conversations about reallocating someone’s talent in the company or letting them go shouldn’t come as a surprise to anyone.

“People know when their role isn’t right,” says Ian. They can feel that they’re not performing like they used to and not helping the company in the way they want. You should always strive to place people in position where they’ll succeed, but when the time comes to pull the plug, you just have to do it.

Great customer satisfaction is key to retention

For the last four years, Sailthru has served big names like AOL and Huffington Post.

According to Ian, the key to this is paying attention to the core meaning of SaaS.

SaaS = Software + Service

A software product that can solve problems that other softwares can’t is a great thing. But what goes hand-in-hand with that is caring about your customers and providing great service. Having a great customer success team in place can really help the company survive, especially in times when the product falls down.

“We look at ourselves as strategic partners for our customers,” says Ian. “Fundamentally, we’re driving massive revenue for our customers: their success is our success.”

Finding great technical talent when you’re not an expert

Automation and personalization predictions are some of the coolest features of Sailthru. Being able to figure out how to do that stuff is data science at the intersection of mathematical modeling, machine learning, and having the setup that’s capable of processing vast amounts of data.

But you’ve got to have people figure all this stuff out for you. “Software is a human capital business,” says Ian, “and having the best talent wins.”

Given the example of hiring a data scientist, Ian said he had to personally interview around 20 people to find the right person for the role. And even though he’s not a data scientist himself, he said he knows enough to have a conversation with someone to be able to evaluate their level of expertise.

A technical company’s founding team should be all technical

A core technical team is important, especially when hiring technical talent. It can be difficult to evaluate potential hires to find the right people who can work to grow your company in the best way.

Ian says it’s at least important to be able to speak technical language, even if you’re not an expert in the area you’re hiring for. “Nobody has every piece of technical knowledge,” he says, “it’s too big. But if you speak the language of technology and you understand how to think about mathematical, engineering problems then you can speak the language of somebody even if they know a specific technology that you don’t.”

The ins and outs of pricing psychology

“I actually find pricing really fascinating,” says Ian, “because it’s a technical problem, it’s a business problem, it’s a sales problem, it’s a psychology problem, it’s a messaging and marketing problem. Price is a signal that embeds so many different things.”

Though Sailthru started at a $30/month minimum, they’ve raised their prices.

By experimenting with different approaches, Sailthru now uses a user-based pricing model, but charges at a premium because they know their product offers far more for in comparison to the competition.

Hustling to the top

Sailthru got their first customers by the sheer hustle of using their networks, making connections, and working hard to get their product into the hands of the right people. They didn’t do much of the free trial strategy, because people are always ready to say nice things about free stuff. Instead, they found charging a fair price up front gave them the real feedback they needed to iterate their product and make it what it needed to be.

From there, they grew by constantly adapting their company to the changes that came with growth and learning along the way.

[spoiler title=’Transcript’ collapse_link=’true’]

Eric:    Hi everyone. Welcome to this week’s edition of Growth Everywhere where we interview entrepreneurs and bring you business and personal growth tips. Today we have Ian White CTO and co-founder of Sailthru. Ian how are you?

Ian: I’m great. How are you doing?

Eric: Good. Thanks for being on the show. Why don’t you tell us a little about your background first and then we can jump into the company.

Ian: Absolutely. Sailthru really came out of a meeting between [INAUDIBLE 00:00:28] and my co-founder Neil Cable. I’ve been programming my whole life. I’ve been building things since I was 10 years old. Went to Brown, started in computer science and theater. I had a background in both and I moved to New York City. When I moved to New York in 2005 the texting was really in its infancy. There was a little bit of a hangover from the dot.com era. I moved into the city and one of the first people I met was Neil who was a CTO at a company called Money Media. It was a financial publishing company, later sold to the Financial Times. We worked together there for a year or two. We had the problem there that all the users, it was financial publishing for folks in the mutual fund industry, and they would get content everyday sent to them at the beginning of the day, it had to emailed right on time, and we wanted to make the content that people got, specific to that individual, but there wasn’t a great way to do that. We used an email vendor for that which was not a very sophisticated vendor, the APIs kind of sucked. So, we had that challenge, but we solved a lot of interesting scaling problems at that company. Then we worked together at a few other different companies. We were at a company called Music Nation which was a startup which didn’t really work out so well, but it was while we were there that we came up with the initial idea that became Sailthru which was; what if we had a technology that truly personalize one to one communication on an individual basis. What if we could do that not just in email, but we could pull together a user’s data from onsite, their whole click stream activity, what are they clicking on, what they are looking at on the site. Later on we added mobile to the equation, and of course shopping cart activity; what are people buying, what are they adding to their cart. If we could pull all this together and form a unified picture of each individual, then the way you communicate with those people could be totally personalized and individualized. It’s really the set of technologies that are available now for personalization for big data, for building interest profiles on users. It’s just different than the capabilities 15, 20 years ago. We were able to build a communications personalization platform natively on top of new sets of technology. I used MongoDB as a really great one for time data store when we were sort of building out the product. At the same time I had been over at Business Insider. I was just technical person over there. I built out the initial tech infrastructure for them. That was a sister company of MongoDB. I started using MongoDB in production there. I think I was the first person at MongoDB to use MongoDB in production. I was able to use my experience with Mongo, specifically it’s a real time capabilities, to build out the infrastructure behind Sailsthru.

Basically we incorporated the company in the fall of 2008. We’d been working on the prototype and bootstrapping. We incorporated the company. In the same week, we incorporated the company, Neil got married, and Niemen Brother’s crashed.

Eric: Oh. Fantastic.

Ian: So, it was a busy week in September. It was basically probably the worst time to start a company in the last several years for sure. Certainly since the first dot.com bust. We really had to bootstrap for a little while. But in some ways that was good because it allowed us to really focus on building out the product, building out the capabilities of the product, making it better, starting to get those early customers and advocates that believed in the technology, but knew that what we had at that time wasn’t that sophisticated in terms of the full capabilities, but we iterated really fast, took a lot of feedback, and really drove forward. At that time, sending an email, every piece of content in that email is completely personalized and recommended for the user. There was a lot of skepticism frankly. People were, “We have email editors who; their job is to go in and pick which content goes where. We know better than an algorithm. Humans are always going to pick out the best story.” Well, humans can be good at picking out the best story or the best product, but not for every single individual person. Proving out the technology and proving out the use case through AB testing and demonstrating the type of list and type of results that we were seeing was really important in those early days, and just building out the tech.

2009 came and went. It was a real time of growing and building. Towards the end of 2009 it was—I feel like, in New York where you started to see the whole environment start to accelerate and start to pick up. Its 2014 now. I’d say when you really look at the growth of New York tech, it’s been like the last five years is really kind of the arc of it, getting more and more activity every year. By the end of 2009, beginning in 2010 we were in a positions to start raising some money—

Eric: You guys bootstrapped for two years?

Ian: We bootstrapped for two years, yes. Basically, we talked to a lot of great New York investors, raised a seed round of one million in June of 2010. [INAUDIBLE 00:07:37] and led but there were seven different great VC firms involved on that C round. That capital really helped us in terms of accelerating the growth of the business. It allowed us to hire our first account managers, our first sales reps, and really be able to just accelerate what we were doing. That period from 2010 on, in the last four years we’ve just grown massively. We’ve gone from the founders to about 170 employees. We have offices in four cities, including L.A. where you are right now. We have an office in L.A., San Francisco, and London, I’m actually heading out to the London office this Sunday, and we’re headquartered out of New York City. Most of the company, most of the staff is here in New York. This is where our engineering is headquartered and this is where most of the activity takes place. But all those remote satellite offices are very significant as well. They’re all about maybe 10 folks per office.

Eric: Got it. Can you talk about that experience bootstrapping in 2008 to growing to 170 employees? What does that story look like?

Ian: When I look back at the last six years its almost many different companies. When a company is growing as fast as Sailthru has over the last several years, things change really quickly and the dynamics of just a couple people in a room verses a slightly larger team of maybe 10 to 15 people—10 to 15 people, totally different company for [INAUDIBLE 00:09:39]. Then you take it up to 25, 30 and that’s a fundamental difference too because at 10 or 15 everybody knows what everybody else is doing. You get to 25, 30, you need a little more process, a little more structure. You continue scaling that and at every step of the way you have to keep questioning your current process and keep changing it.

[00:10:05]

People whose roles and skills make sense at one environment might not make sense at another, maybe not in the same role. You just have to—growth, technology, these things inherently mean change. One of the things you just have to do is keeping responsive to change. There’s a lot of different challenges. I could talk about the growth of the tech team, especially from my perspective, but really, all across the company it’s been about eight different companies and there have been a lot of people who have been with us the whole way, but it just keeps changing and you have to really be responsive to just what the current challenges of the situation are.

A SAAS company, it starts to take on some momentum. It’s like a boulder rolling down the hill. You generate more recurring revenue. That drives the success the business. You can scale, you can grow when you have that customer base that is loyal, that sticks with you, that you’re building on top of. But those early days when you’re bootstrapping it’s really just about finding that product market fit at all because you have a product vision, you have something you’re trying to build, and you put it in customer’s hands and you start to see what works. In the early days, certainly from a technology and products standpoint, we would try out lots of different ideas and see what would work. It becomes very important to not get too attached to the ideas that don’t work out, kill them quick, then double down on the ideas that do work. Trying to be data driven about those types of decisions, but in SAAS with B2B you know your customers. You sit in a room with your customers, you’re on a call to your customers and you can hear from them directly about what their pain points are and how your software that you’re building can either help them or is not meeting their needs. As much as you try to make decisions on the most objective sort of set of framework that you can, a lot of it is really just synthesizing what they’re saying, what their problem is, and how rapidly can you deliver something that solves that problem. It really is the 80/20, especially in the early days. There’s a lot of ways you can deliver a feature or a result with a very high power to weight ratio, where you can develop something and it can really swing a big impact for a customer.

At the same time when you’re small and you’re dealing with customers—we have some just fantastic brands. Four years ago we were working with Huffington Post and AOL, they’re still clients today of course, but especially for us as a very small company you don’t want to let a customer or a single customer dictate your entire strategy. It’s really important to find the right balance between what are the things that— sort of synthesize and hear what they’re saying and fit that into the larger vision. This sort of all make sense?

Eric: It does make sense. One thing that really hit a point; I’ve talked to a few founders on this show and someone that’s a fit in a certain point that is no longer is a fit at another point—I read this article in Harvard Business Review where Netflix, before they were sending CDs and then some people just weren’t a fit when they moved into the streaming world. How do you have these conversations? Can you give me a story or an example where you’ve had these tough conversations with people?

[00:14:53]

Ian: It should never be a surprise if someone isn’t right for a particular point in the company. I don’t want to talk about a specific individuals or anything of that nature, but what I’ve found is people know when their role isn’t right. When people are in the right role everything is executing, results are happening, you can set objectives, and hit those objectives. When people are just sort of not there everybody can feel it. What you try to do is put people in the position where they’re going to succeed. That’s just what you do. With a startup, with a high growth company, everybody’s going to grow and I’ve seen some individuals who have been with this company grow so much over the last few years. But you have to do what’s best for the business.

Eric: Okay. Now, 170 employees and what do revenues or number of users look like today.

Ian: I can’t talk about revenue. We’re a private company. We don’t disclose that. We’ve got about 400 customers. We have deal size that goes into the low seven figures. I can tell you that our revenue growth has been very large. We were number 30 on the Inc. 5000 last year, and the second fastest growing company in New York on that ranking. We’ll do more revenue this year than the prior three years combined.

Eric: Nice. You have Huffington Post and AOL for the last four years. That’s crazy retention. What do you think you guys do that stands out in terms of retaining customers?

Ian: SAAS stands for software as a service, and there’s really two components to that; software and service. I think providing good software that solves problems that other technologies can’t do is really important. Your need to differentiate a product in the market is inherently sticky. But what comes with that is providing great service and caring about your customers. That’s everything, making sure our customers success team is right for any SAAS business. I think is a really critical component. When you have a great customer success team and when there have been times when the product has fallen down, the customer success team can really help make things work for the customer. I think our customers are loyal to us because we provide unique value and because they trust us. Fundamentally we’re driving results. We’re driving massive revenue for our customers. Their success is our success and vice versa. We look at ourselves as strategic partners for all of our customers. The account management will do a strategic review with every single one of our customers and look at their metrics, look at the KPIs, look at the drive through the platform, look at how can we work together to build a personalized marketing strategy that is going to drive your revenue or drive user engagement. I think customers really appreciate that.

Eric: Got it. By trade I’m an internet marketer and the stuff that you’re talking about right now sounds like it’s a great marketing automation. Do you do anything in that world?

Ian: Yes. Absolutely. Automation is a big piece of the platform. What we really do is; we ingest this tremendous amount of data in real time. Every page that’s happening in real time in all of our client’s sites, that goes to a [INAUDIBLE 00:19:17] in real time. Every purchase or shopping cart activity we now have an IOS and Android mobile app. All that data flows into Sailthru and you can chain events and triggers to any of those events that are flowing into the system. You can take action on anything that goes on and set up a series of automation. You can say, “Okay, if this event happens and this criteria’s fulfilled, take this action.” and then what’s really cool is we just introduced Site Lines [ph 00:19:52] our predications product so you can take action not just on the events that are happening in real time, but you can take actions on predictions using machine learning models of what users are likely to do.

[00:20:04]

You can basically say, “This user, you Eric, you’re really actually likely to opt out. We’ve made a prediction today and we predict that you’re in the top 0.1% of users who are most likely to opt out because we’re sending you too much email. We’re sending you too much volume of messages. We send you another email there’s a high probability you’re going to turn out and you’re going to be gone.” So, what you can actually do using our tech automatically is just say, “All right, the users who are in that high K tile are very likely to opt out, just don’t send to them. Then the predictive model we’ll start to even out the flow of the user naturally because the probability of the user to opt out declines and you automatically have predictive cadence automation. It’s really cool stuff. I get excited about it when I’m talking about it.

Eric: Where does someone go to learn about predictive cadence or whatever the stuff you’re talking about right now, it’s going to be super important, it already is super important, so how does someone learn this stuff?

Ian: I guess there’s learning about it from a marketing point of view, or what it’s capable of doing. There’s learning the technology behind it.

Eric: That part.

Ian: The technology behind it really comes from data science. Data science is such an overused buzz word I guess, but it really does represent a very specific set of skills, the intersection of mathematical modeling and machine learning, and having an architecture that’s capable of synthesizing and processing all this data. I think, certainly for any company that’s in our type of space, building a really strong data science infrastructure is important, and a team because software is a human capital business. Having the best talent wins.

Eric: You and you your co-founder, initially when you guys first started, you start to get bigger to 100 -170 employees. How do you find out whether the person, like a data scientist that you’re hiring actually knows what they’re talking about when you yourself, you’re not an expert in that field?

Ian: I’m certainly not an expert, but I know enough to have a conversation with somebody and be able to evaluate their level of expertise. When we hired our chief data scientist through Germa Stanley [ph 00:23:01] I probably personally interviewed at least 20 people for the role. We found the right person based on technical evaluation and also personal evaluation. I think the important thing, if you build technology, you can’t know everything. Nobody has every piece of technical knowledge. It’s too big. If you speak the language of technology and you understand how to think about mathematical engineering problems, than you can speak the language of somebody even if they know a specific technology that you don’t know. What becomes really challenging in tech is when somebody who doesn’t actually have a technical background tries to evaluate technical folks. That’s why it’s so critical to have a technical founder and we were really fortunate in our case because we have three technical founders. Neil, the CEO is himself a former CTO of many different companies. Chris our VP of engineering is just a brilliant OPs guy. When your building software I think it’s really important for the founding team to all be strong in software, in technology. If you’re building an internet business where the business is fundamentally not software, like you a pure player e-commerce and you sell fashion online, then I think it becomes much more important to have somebody on the founding team who has really great expertise in that industry. But technology, you’re got to be technical. It’s just essential.

Eric: Got it. Going back to the data scientist question, you’ve interviewed 20 people, everyone’s trying to hire data scientists nowadays, where do you go to find this talent?

Ian: We did a routine search for that, although, the person we hired we wound up getting through referral actually. We interviewed a very strong candidate for a different role who loved the company and really wanted to join us. It didn’t work out for various reasons, but he actually referred us Germ [ph 00:25:43]. Thanks to him. He knows who he is.

Eric: You talked about the three founding—your cofounder being, you guys both being technical. At one point do two technical co-founders decide, “You go do this, I’m going to go head up operations divisions and keeping cash in the bank.”?

Ian: It was always clear that Neil would be on the business and sales side. But the reality, especially in the early days, everybody does a little of everything. But Neil really just—he would be the person I could bounce ideas off of because of his level of expertise. We really speak the same language. Especially in the early days—this is why it’s so important to have a pre-existing relationship of some kind with your co-founder. If you just sort of paired up to get into YC [ph 00:26:49] or something, I don’t know, I can only speak for myself, I don’t think I would be able to go on a seven year and more journey with somebody who I just paired up with—you know what I mean. You need that trust and that shared communication where you’re on the same page. Especially in those early days when we just have to move really fast the fact that we could both think about the product and what it required in the same way, Neil would be the person who was more meeting with customers, meeting with prospects, he was playing the role of head of sales and head of products. Being able for him to be able to relay that back to me from the field, of course I’d been meeting with customers too, but we had that split in the nature of responsibilities. It’s important for it to be clear like, He’s a CEO, I’m a CTO. Ultimately if we disagree about something it’s Neil’s call and I’m find with that. We have that shared trust and respect. If I disagree, that’s fine, we’re going to on with our lives. It’s better to make a decision than to not make a decision because nobody wanted to be clear about it.

Eric: Got it. Okay. You guys started in 2008 and now you guys are closing figures in the low seven figures. How did you guys discuss pricing? What’s the psychology behind that?

Ian: Our original pricing was a minimum of $30 a month and it’s a lot more than that now. Pricing is really hard. I actually find pricing really fascinating because it’s a technical problem, it’s a business problem, it’s a sales problem, its psychology problem, and it’s a messaging and marketing problem. Price is a single that imbeds so many different things. You want to charge something that’s going to make sense to customers. You want to charge something that is going to line up with the value that you’re providing. We tried a few different models. We now look at it as a user based model because at the end of the day the most important thing that Sailthru does is store your data about users in a platform with the means to act on it, unify all your user data, give you the means to act on it. So, pricing on that number of end users that you have makes the most sense, but you have to look at the market, you have to look at what the competitors, that you’re up against deals for, are doing.

[00:30:10]

We’re often up against deals with legacy email providers. They don’t do all the stuff that Sailthru does so we charge at a premium to them, but we want to make sure that our pricing is not going to be way off the mark to the point where the prospect is going to say, “Wait a second. There’s a lot of visits over here.” and this is just a completely different paradigm.

When you’re entering any kind of market you’re either a premium product that provides unique value and you charge a higher price point, or you’re the chief disruptive product and you charge at a lower price point. You don’t really want to be caught in the middle. Understanding where you sit in that market dynamic. We’re a premium product. We’re the best in our space at what we do. We charge for that value. Does that make sense?

Eric: Totally makes sense. Maybe you need—I think I’ve purchased a few pricing psychology books and I think I’ll have to put these in the notes. Do you have any books like that? You guys read anything like that?

Ian: Actually I have not read a book specifically about the psychology of pricing. I read a lot about the topic. Do you have a recommendation of your own?

Eric: I forgot what it was. I purchase so many books. I have a stack of Amazon books on it. There’s unopened right now, but I’ll put it in the notes and let you know too. I think there’s a really good one. Moving on here you guys have 400 customers now. How did you guys, I’m going to call these mostly enterprise customers, how did you guys get the first, let’s say, 20, 30 customers?

Ian: Sheer hustle. If you have an unproven product that you’re still working on, finding the product market fit, you just have to go out there and knock down doors. One thing that helped was we were able to use companies that we knew personally. Like, “Hey. Try out our product.” Give it a shot. Those kind of early customers were really helpful because they’re friendly folks who will give you feedback. But you have to be providing value. It doesn’t matter if you’re friendly with somebody. If you’re product isn’t any good and it isn’t providing value, nobody’s going to use it. It really boiled down to just using our networks and context and getting the product to the right people. But from there you think about the adoptive curve, what’s the most important thing in the early adopters stage is references; word of mouth. To this day the best leads you’ll get are from referrals from our customers. We just had—on Wednesday we did our first ever customer conference, Sailthru Lift 2014, which is a huge milestone for the company. One of the things that was amazing about it was getting so many of our customers in one place, talking to each other about all the great things that they’re achieving using Sailthru. Building that type of community and loyalty around a product is just so important. It doesn’t stop being important as you scale. If anything it’s more important, but certainly in those early days you need those early reference customers who love the product and will get on the phone with people and talk about how much they love the product. That’s really important.

Eric: Got it. When you gave these away in the early days did you give them away for free or did you start charging them off the bat?

Ian: The very first prototypes might have been free. We charge very early on because—it’s a better test. When you can—people will always accept free shit, right? But if your say, “Here use this instead of what you’re using. We’re going to charge you a fair price for it.” Now you know if what you built is actually valuable or not. We were charging paying customers from very early on.

Eric: Got it. Switching gears a little bit. Going back to 2008 to know. What’s one big struggle you faced while growing the business?

Ian: I think the fundamental struggle is always hiring the right talent and putting them in a great position to succeed. That never stops. It’s always a challenge, especially hiring technical talent. So many great startups, so many great companies, and you want to keep the bar high and hire the best talent you can find. We’ve gotten a lot better at it over the years. That’s always the biggest challenge, making sure you’ve got the winning team.

Eric: Okay. You talked a little earlier you’ve gotten referrals, there’s also, we’ll call them recruiting firms, what else do you guys do to keep that hiring pipeline going?

Ian: We use a lot of different tools. I think we hired an in-house recruiter maybe earlier on than some people would think—it was probably when we were about 20 or 25 employees we hired our first full time in-house recruiter. That was a good move. I would recommend that again. I think we hired a second recruiter not long after that actually. Today we’ve got a larger talent team. We have a dedicated technical recruiter, all of those pieces. External recruiters are what they are. There’s some good ones to work with. There’s some not as good ones. But nobody is going to be able to sell the company, understand what the company needs, present the vision and the culture as well as somebody who’s there every day and understands it. That’s why having a full-time recruiter, I think, is really valuable. And there’s no substitute for founders or leadership being directly involve in the recruiting process. Now, it become challenging as you scale. I’m not on the phone screens anymore, but I do meet with almost every engineer that we hire, or if I don’t Chris does, because we want to make sure that we’re presenting the business and the vision of the company in the best way possible so that, even if we don’t hire that person, we want them walking away feeling like, “This is a great place to work.” because it really is. This is the best company I’ve ever worked with. I’m a little biased. It shows the candidate commitment. I just think it’s important. If you’re a leader at a startup recruiting is a big part of your job. I just is. It’s a pain in the ass sometimes. It can suck. Interviews are not always fun, but it’s really important.

Eric: Couldn’t agree more. Maybe I can get a check list from you after the interview. Moving on. What’s one piece of advice you’d give your 25 year old self?

[00:39:04]

Ian: Oh man. My 25 year old self. Gosh that’s hard. I just think, “Be ready for change and believe in yourself. Believe in your own ability.” Nobody in this world really knows what they’re doing. Everybody is learning every day and just learning new things. I think when I was 25 I still felt like a kid. I felt there were so many people out there who were smarter and more experienced than me, and better, and I just didn’t know anything. To some extent that was true, but you have within yourself a lot more resources than you always believe you have. Everybody who’s ever achieved something great has struggled with doubt and uncertainty. Getting comfortable with that uncertainty and then just going on to do what you’re going to do anyway is one of the most important things. There have been so many ups and downs during this journey I’ve been on. Any startup is like this. There are days when you’re on top of the world and there are days when it looks like everything’s falling in under you. Being able to ride that out with some real belief in yourself is what’s important. Over the years I’ve gained more of that confidence that I definitely didn’t have it when I was 25

Eric: I love it. I love that quote, “Nobody knows what they’re doing.” I think that’s actually pretty true. Final question from my side. What’s one must read book you’d recommend to the audience?

Ian: I’m going to recommend a blog actually because I think SaaStr  is the best S-A-A-S-T-R-E.

Eric: Jason Lemkin’s blog.

Ian: I love his blog. I read it. When I discovered it a year or two back I reread all the archives and he was talking about all these things we had experienced and gone through and I was like, “Oh yeah.” I continue to read his stuff because I think it’s great. A book that people should read; I’m reading Peter Theil’s book right now and I really like it. I don’t know if that’s the one book.

Eric: “Zero to One”?

Ian: “Zero to One”, yes. I just enjoy it. I enjoy anybody who’s a contrarian and thinks about things a little bit differently. I always enjoy and interesting point of view on the industry. That’s what I’m reading right now and enjoying it.

Eric: Nice.

Ian: So many different books that I’ve read in my past. I can’t pick one.

Eric: Zero to One is a great book, and SaaStre. I call it Saastrength because it’s like str, but anyway. Everyone this is Ian White from Sailthru. Make sure to check out Sailthru. It sounds like there doing some cool stuff. Ian I think there’s a lot more stuff to talk about in the future, but for now we’re out of time. Ian, thanks so much for joining us.

Ian: Absolutely. Thanks a lot Eric.

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