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How Max Altschuler Grew SalesHacker From One Conference to a Media Company Serving Millions

Max Altschuler is redefining what it means to build a successful career. When most people were busy trying to land internships in college, Max got his school to agree to pilot one of the earliest bike sharing programs. When that business failed to raise the necessary capital to get off the ground and Max found himself without a job as he graduated into one of the worst economies of the century, he started a social media consultancy that generated revenue within its first 30 days.

In this episode we break down how these experiences led Max to become a self made millionaire by the age of 30, forever changing how he thinks people should approach their careers. In his new book “Career Hacking for Millennials: How I Built A Career My Way, And How You Can Too” Max tells his own inspirational story and gives highly specific actionable advice for anyone that needs direction with where to take their career.

We also talk about how he was able to overcome some incredibly difficult moments in his entrepreneurial journey, and how he’s designed his life to be able to run three businesses at once – Sales Hacker, Career Hacking, and Sip Sutra.

Full Episode Transcript

Max (01:16): Most of the time, this is what I like to do. So where most people are binge-watching Netflix or getting into Game of Thrones or going out and playing a round of golf, I’ll stop working on Sales Hacker but start writing a book or start work on Sutra, which is our healthy coffee alternative. We just got into The Bean. The one on 2nd and 3rd street – that’s another company that I started with my girlfriend and another guy – and we’re doing I think like $15,000 a month now in sales. It’s like I love this shit. This is fun, you know?

Vadim: Was Sales Hacker your first company?

Max (2:07): Well, yeah – my first company that successfully launched. In college I had a bike share program called Rack and Ride. We were way too early to the US, but I had lived in Barcelona for a year. I was an architecture major when I was in Barcelona, and around then the housing market crashed. I called my dad and I was like, “I love architecture, but I’m not going to have a job after college. What the fuck am I going to do?” So he’s like, “well, maybe you should just start diversifying your classes now, and you can always go back to architecture.” So I started taking business classes, merging with my design classes. All I really want to do is start my own business. And they had this amazing bike share program where you swipe your card, your membership card, take out a bike, ride it to another rack and another part of town, locked it in. And then you never had to worry about that bike again. So it’s like, let’s bring this to Arizona State.

So I actually won a business plan competition with two of my buddies at Arizona State. And then we got exclusive rights to commercial bike sharing, signed off by the university. We had a university architect sign off on our locations, and we got pretty far with it, but we couldn’t raise the money needed. And again, this is now 2009, so we’re three 22 year olds trying to raise a couple million bucks for manufactured bikes and computers and it just wasn’t happening in that economy, right after the recession we’ve just gone through – but I’m so glad it didn’t happen because it would have been such a pain in the ass. There’s so much liability and insurance and all these different types of things.

Then in the news yesterday, Uber just bought a company for $100 million – that does dockless bike sharing. And then I saw Arizona State just launched a couple of different bike sharing options. So, you know, 10 years later the timing is a lot better to the market. The recession is way in our rear view mirror. I don’t think we’ve ever had a better economy than right now and it’s just been easier to raise money and get these things to market. So I don’t know, I’m glad that didn’t work out. After that we went and started a social media management company for small businesses and so we sold to real estate agents, bars and restaurants and our goal was to make American money while living abroad. So we took it to Costa Rica and Nicaragua and ran it there for three or four months. And, after that we were kind of just sitting there in the kitchen – drank a ton of coffee, a bunch of alcohol, and we were just having fun in Costa Rica and Nicaragua and we were like “it’s time to get serious, what are we going to do next.”

Vadim: Who’s we in this case? Were these people from college that you already worked with that you wanted to work with again?

Max: So the two guys that I worked with on the bike share program were two of my close friends from college. After the bike share program kind of fizzled out, I had just graduated, one of them went to Argentina to do a six month program in something, I forgot what it is, and the other one ended up going to work on as like a deckhand on yachts. And then when I went to do this social media company it was with two other buddies from college and one at the time was working for Enterprise Rent a Car. And the other one was a PA. Getting coffee and bagels for people in Hollywood, you know, that kind of job.

Max (05:07): And so they were both like jumping at the chance to do something else. So we sat in a room in my apartment in Arizona after I graduated. I still had the apartment for like another month or two and we sat there for two weeks with a bunch of red bull and adderall and um, you know, five hour energies and beer or whatever we needed and cranked out a business and we sold $5,000 in the first two weeks worth of our product. And we’re like “oh, we gotta fit here, let’s figure this out.” So over the next month we kept selling. We said, when we hit a certain number, we’d pack up and go down to Costa Rica. So we hit the number after the first month, went down to Costa Rica and I think we did like two months in Costa Rica, two months in Nicaragua or something like that, give or take.

Vadim (05:49): Wait, this was for fun or this was to get customers?

Max: This was to work. We were able to run a business making American money, getting American customers by calling instead of doing face to face. So we were able to get new customers, and service those customers, and do everything from Central America, without having to step foot in the US. So our cost of living there was low, and we actually had enough money to pay for a fourth to come down, who ended up being our designer. He was another guy and another friend of ours who did the architecture program and was like, “all right, before I get into my first architecture firm and start, you know, breaking my back again, I’ll come down and join you guys and I’ll do the design for the campaigns that you’re running.” So we were running social media campaigns for like the John Wooden award.

Max (06:33): It was like a marketing web development agency and this was back when you can build little websites within your Facebook page, so you remember like the Skittles and Starbucks sites where you can actually click the tabs and they had like little animations or games or giveaways you can do inside your page. And it was built inside of the iFrame that they had. So I think this was like 2010, 2011 around that. We dabbled in the affiliate world trying to figure out if we can run an affiliate businesses. We try to start our own companies and we just didn’t have the experience. So eventually I parlayed that into a job at Udemy and I was the second business hire, and first guy focused on the sales side of their marketplace.

Sergei: How big was the team when you joined them?

Max (07:20): There were four in the US and I think another three or four in Turkey. So the two founders, Eren and Oktay, were both from Middle Eastern Technical University. We had dev resources in Ankara, Turkey and then the business side of the business and the two founders were in San Francisco. And I just saw the potential there. It was like a marketplace for continued education. Sounds genius. We were using Udemy and Lynda to learn in our previous business when we were building out these sites and these Facebook pages. So we knew that there was a real application there. And then the economy that we’re in now, looking back on it, it’s like you don’t need to go work for a corporation, you don’t need it. Everybody can work for themselves now and be a freelancer – we have an intern working for us on Sutra and I’ve taught her how to build out these Instagram profiles and pages.

Max (08:18): And so she knows how to take pictures. Now she knows how to lay them out so that each picture kind of creates a larger story. She knows how to write the captions. She knows how to actually optimize for growth. She knows how to do like the little icons on the stories. If she wants to after this internship, she can go to a bunch of small startup brands and charge him like a thousand or $2,000 a month – get 6 to 10 of those. That’s probably not even a 40 hour a week job. She would be making good money right out of college. She doesn’t need to go work for anybody. So like there are lots of little things now that you can do as a freelancer. And these companies like Udemy and Lynda, I mean to be able to teach people for $49 something that they can then learn how to do and then go sell to other people. I mean it’s the best arbitrage that there is – the best learning that you can get now.

Sergei (09:05): I think you’re absolutely right that anyone can sort of be their own boss now. I think if they have the confidence to be able to get customers. But you know, for somebody that’s just starting out, for example, like your intern, if she told you, “hey, I want to go off on my own after this internship” – what sort of sales advice would you give her? If you had maybe a few hours just to show her and train her, what would you tell her to do on a daily basis to get those customers?

Max (09:34): Yeah. I’d tell her to go out and find companies like ours. I mean, we had a need for her fortunately. My girlfriend before we were running Sutra was a marketer, specialized in influencer marketing type stuff. So she’s really good at Instagram. She was really good at going out and getting affiliates and working with people that were in the space. So reaching out to people who might be interested in a product like ours, getting them to post it on their stories, on their Instagram, on their blog if it was something that was relevant. So that’s what she’s doing for Sutra. And she hired these interns and she’s training them to do little pieces of that. So we have another one that’s writing blogs for SEO.

Now the intern is becoming an expert in this nice little niche thing and can go out and find companies like ours and sell to them for whatever they’re willing to pay. So let’s say I’m Sutra – a healthy coffee alternative, early stage company. What other companies are in a similar space to ours? Well, there’s like 4 Sigmatic, and Dirty Lemon, which does like activated charcoal lemonade. There’s Ample, which is a keto supplement powder drink that you can just pour water in. It’s like a protein shake. I see a different one every day where I’m getting targeted on Instagram, so you can go on there and just find a bunch of really early products and go to them and say, “Hey, I noticed you don’t really have an Instagram strategy, – I’ll take it over for you and it’s a thousand dollars a month and here’s what I did for Sutra” and I’d be happy to give her some stats from before she started and now, so she can show them her work – even if it’s not the best story, I’ll help her make it into a story that she can show other companies. Put together a little case study or something like that. After working with us for two months she can use this story to sell to another company.

Sergei (11:31): There’s a lot of let’s say self proclaimed social media experts out there, but maybe they could easily go and build an Instagram page and buy up a bunch of users and say, “Hey, look, I have 30,000 followers. I can do the same for you.” So how would she stand out from the noise and how should she reach out to these companies to actually get their attention?

Max: I don’t know if I’d go the route of a building out, I don’t know, some crazy Instagram page for myself with a bunch of paid followers or anything like that. I think what she should do is have our own page that’s obviously optimizing the way she wants to optimize this. So if somebody is going to look at it, they can say, “oh, well, uh, you know, yours looks pretty good,” but really it’s not about her and her own individual brand. And if she was selling it, I’d say “yeah, I don’t really do much for my own personal page. It’s not really the point. Here are the people that I’ve worked with before, they’re businesses, they’re just like you.” So I think that’s the first thing. I don’t even know if she really needs a landing page. She can just use us, but yeah, sure you can go on Instapage and build that landing page. You can probably get somebody on Upwork to do it for, you know, I don’t know, a hundred bucks or something like that to do a decent enough job just to have like a signup link and you know, Stripe account connected to it or something like that. But the main thing is just going out and doing the research on the other companies that are in the space. So sit down, set up a spreadsheet in Google docs or Excel or whatnot, or even just a pen and a paper and go down and make a list and see if you can find 200 companies that are similar to ours that you can go out and prospect into and then just slide into their DMs.

Max (13:12): Odds are that they’re posting, but their posting is terrible. And I’ve seen this a million times. We’ve done competitive research, we’ve gone into other people’s pages and been like, “this is terrible. What the fuck they doing? Like why can’t they figure this out or, or why haven’t they paid attention to this” because this is one of our best channels. Doesn’t make sense to neglect it for as cheap as it is to be able to get somebody to do it. I mean we had an intern doing it with a little bit of tutelage from Ashley, my girlfriend. So now you know, you start at $500 a month or something like that and get a couple of customers. I think she could – it’s better than going and I don’t know, making three or four grand in her first job and she’s in Miami. She’s not in New York. So you know, her first job is likely to be in the $30,000, maybe $40,000 range. Whereas in New York, maybe it’s a little more because you factor in cost of living.

Vadim (14:02): So you started – just from reading up about you – you started Sales Hacker because I think, well probably there was some natural pull there, but also because there wasn’t, from your perspective, a structured way to teach sales or learn sales for people, but you yourself were able to kind of figure it out. Along the way you started a couple of businesses. Do you think you’re a natural salesperson and how did you gain the confidence, especially out of college to pick up the phone? I’m assuming you did some cold calling back then because it was a little bit more appropriate back then, but yeah. How’d you get the confidence? How’d you know “what am I going to say to these people?” Did you read up about it? Did you self educate? What was the process there?

Max: There was a lot of self education. So I never done a proper sales job before. I’ve never worked for like a proper VP of Sales or Head of Sales or anything like that and never had a sales mentor, but my dad was a financial advisor and when you’re a financial advisor it’s all about relationships and understanding how to talk to people. So I like to think that I had the natural social skills and really social awareness to be in sales and I think that’s the main piece is understanding social situations and social awareness. I had somebody, I think it was Steve Blank, we were trying to get him to teach a course. It was Steve Blank’s like number two guy or something like that. We were trying to get Steve to teach a course and he was like, “you’re like a pitbull on a meat truck, but you’re doing a great job of being persistent without being pushy or pesky.”

Max (15:33): And I was like, all right, that seems like what sales is to me. It was like, all right, how do I stay on top of this person, make sure I’m following up consistently. And at least adding some kind of value when I follow up so that this person doesn’t get a negative opinion on me, but I’m still making ground on this sale. And it’s really just about understanding those boundaries. And then from there, you know, there’s a lot of other pieces that connect, like I had never been in sales before. I had to kind of self educate, you know, I read a couple books. The first book I read was the Greatest Salesman in the World by Og Mandino. And that was more laying out like the principles of sales and the right things to do. But then there’s more technical books like Aaron Ross’s book, Predictable Revenue, or my book Hacking Sales that I ended up writing. I wish I’d read Aaron’s book earlier because I ended up building out most of those processes.

Then I read that book and I was like, “damn, I should have read this book six, seven months ago. I would’ve been in a much better place.” But you know, I think the main thing is just undeniable passion. I don’t think it was really the founders of Udemy – I know that some people buy in to this, you know, “drinking the Kool Aid” type thing or like, oh, we’re going to change the world. I was actually working for a company that could change the world. We were building a marketplace in the online education space and you know, education is a $2,000,000,000,000 market. You look at colleges and college doesn’t work. College is ridiculous. By the time something makes it into a textbook, it’s obsolete. When I was in grade school, we were learning about how many cells are in a leaf and not being taught about, you know, what APR means on our credit cards or you know, how to do our taxes. The entire system is completely broken. I, for one, as somebody who was basically castaway by my teachers in a lot of ways and was told I had a learning disability. “He needs Ritalin. He needs to go into special classes.” No, it’s because you’re just teaching me the same way you would teach somebody else. Even though we learn in different ways and you’re teaching me the same things even though we’re going to do completely different things and I just didn’t want to buy into that system. So when I went to Udemy and I approached them, I was like, this is where I want to work, this is what I want to sell because I’m super passionate about it.

Max (17:46): When you have that passion and you’re actually something you truly believe in, it makes it a lot easier to sell. So a lot of my dials or my calls, it wasn’t about having the self esteem or confidence to make those calls – I truly believe that this was something that people needed. Not only because this is the future of education, but say you’re an author, you wrote a book, great. The next thing you should do is create a course. If you want to monetize that book, it’s like the only natural evolution from there. You have a book that you sell for $20 a book now create a course. Everybody that bought your book is going to buy your course, so you just go up another level – people like to learn in different ways.

Something written, something visual and of course auditory or actually learn by doing. So if you can train them in all four different ways, you can actually get them to pay four different times for basically the same training.

So I sold and I still do as if I’m a doctor and you know, maybe you have a broken leg and you’re sitting there eating in a restaurant, your bone is popping out through your skin. Like I’m going to fix your leg with XYZ. I’m not going to let you tell me no, this is the best thing for you right now. That’s ridiculous. Let me fix it. So if you sell with that passion and you believe “this is the best fucking thing I could possibly do”, then there’s really no confidence or self-esteem needed because you have this. There’s no other way – why would you not do this? It doesn’t make any sense. So that’s how I approach it.

Vadim (19:22): It’s one of those skills I think that is very transferable, so if you’re willing to put yourself out there, if you have no sales experience and do it for yourself, it’s one of the best ways to do it because if you have that sort of intrinsic motivation, the passion, you’ll stumble a little bit in the beginning, but eventually you’ll figure out the pitch. Like you said yourself, you believe that you’re really addressing somebody’s pain. It’s not going to feel like you’re interrupting them too much even though maybe sometimes it will, but you will get past it, especially once you start seeing that people are actually getting value from what you’re doing.

But you’re creating a lot of content. Now, you mentioned, for example, Aaron’s book – I also read that back in the day – but as you’re creating this content, how do you think about making sure that it doesn’t become obsolete? Making sure that there’s longevity there. I mean, of course with sales there’s certain principles and skills that probably always apply, because it’s about communication and about being able to communicate value to people, but how do you make sure, especially when you’re getting into the nitty gritty and the technical stuff, that it stays relevant?

Max (20:18): Yeah, it’s tough and that’s why you have a blog and a podcast and you’re constantly releasing stuff because you really don’t know where the market’s going to go. There are probably key posts that we put out, and areas of my book, even Hacking Sales, that come May 25th when GDP hits in certain areas or to certain segments of the market, they’re going to be obsolete. Like you’re not going to be able to send emails the same way we told you to send emails years ago or three years ago when we wrote that book – there are different laws that are in place now, and in certain geos you can’t cold email. So it’s just how it goes. So we just want to create content. I sold the rights to that book to Wiley and there are a lot of times where I wish I would’ve kept it self published so I can kind of update it fairly often because it needs updating.

So maybe I’ll launch version two at some point, but for the blog content, that’s why we post four articles a day and that’s why we post from practitioners. So we don’t want to post from people who’ve been authors for 20 years or people who just run the conference speaking circuit or anything like that. We want to post from people who are VPs of Sales at, you know, 200 or 1,000 person companies or more. Let’s say you’re a VP of Sales at a one thousand person business intelligence company and you do something really interesting in your sales process. I want you to write about that because we want to uncover unique nuances or hacks, tips, tactics, strategies inside the sales process that you can’t read about elsewhere. It’s a constant evolution and that’s one of the best things about what we do versus even if sales becomes a college course – I mean by the time you print that textbook, it’s obsolete. So a blog is a really good way, or an online publication is a good way to stay relevant.

Vadim (22:14): Yeah, it’s really smart because either way there’s a lot of content being produced out there. It’s impossible to consume all of it, but by making sure that you’re consistently posting and also to your point, addressing it with practitioners who are practicing it every single day and figuring out new ways of doing things themselves, people will find the content at the relevant time for them, and the content will be something they can use and put to action right away. So that makes sense.

Sergei: So I want to sort of backup a little bit and hear a little bit more about the origin story of Sales Hacker because clearly you identified through your own business a skill that you had, which of course is sales – you actually found a company that you would be really passionate about, you reached out proactively, which I’m sure you cover in your book that’s coming out Career Hacking for Millennials. It sounds like you helped grow sales and grow the revenue engine for Udemy, and later did it for Legal Zoom. There’s other folks that have talked about that story. At what point did you identify a sales conference as a potential business opportunity and not just something you do on the side and how did that even come about?.

Max (23:29): We were growing pretty quickly on the supply side and other founders and VCs were asking our founders how we’re doing it, and we had a couple of really hacky processes that we’ve set up. Batch email sending that made it look personalized, a team of virtual assistants built out in the Philippines that were going out and building lists and using SEO tools to do keyword strings, etc. You have to read Hacking Sales if you want the full background on that. But, it was something that we built from scratch that was completely hacked together, but in a way that was super scalable and streamlined.

And we would build, test, measure and optimize every piece of it – subject lines, call to actions, you name it. So these founders and these VCs were approaching our founders and they would push them to me and I’d have conversations with everyone detailing what we were doing. And it was apparent that there were a lot of people interested in figuring out how to hack the sales process. And one guy wrote an article on how to scrape python – his name was Ryan Buckley – he was the CEO of Scripted at the time. And I saw that article and I was like, “this guy’s doing what we’re doing, we got to connect.” So I met up with Ryan, ended up meeting up with another guy who was the head of sales at Bluekai at the time.

Max (24:58): And then T.K. from ToutApp. And another guy, Matt Ellsworth, who actually applied to Udemy, didn’t get the job, ended up at Storefront. After we interviewed him, he reached out and said “Hey, you know what, I didn’t to get the job, but you sound like a good guy, let’s hang out.” So I was like, ‘sure’. We became really good friends. He got a job at Storefront and was doing a lot of the hacky stuff that we were doing. So the five of us would meet monthly and we would talk about all the different hacky stuff we were doing inside of the sales process and it was super valuable, super beneficial to us. And so we said, “OK, you know, let’s all grow this thing.” Slowly we would bring more people of value and every month we met the group would grow.

And then right when I left the Attorney Fee, when they sold the Legal Zoom, we had a meeting and there was 20 of us in there and I said, “you know, who would be interested if we started a conference out of this.” And in that room I had Jason Lemkin who had just sold Echosign to Adobe. He was attending the group now and he had been writing a lot on SaaStr, but again, this was like 2014. So this was before it was what it is now. It was 2013 actually. We also had Matt Cameron, who just got on to be the VP of Sales at Scripted but was the VP of Global Sales at Yammer before that, when they sold to Microsoft. We had Armando Mann who is the VP of Sales that RelateIQ, which a later sold to Salesforce for like $390,000,000.

Max (26:25): We had Doug Landis, who is the VP of Sales Productivity at Box while Box was still a private company. So we had some really good name guys in there at the time and they all became speakers at the first conference. With ToutApp and Scripted we already had enough money to cover the cost of the conference, from a sponsorship perspective – right off the bat.

Sergei: How did you know how to price the sponsorship since you’ve never done it before?

Max: I just pulled a number out of my ass and said, this is the price.

Sergei: What was the number?

Max: Uh, I think I charged like 15 grand and Ryan was a small sponsors who’d be like $2,500 or something like that.

Vadim: Did you have to commit to saying “we’re going to get this size audience to the group.”

Max (27:13): So actually we said it was going to be a hundred hand-picked and once we got past a hundred I was like, all right, well our space holds 300 and so we just opened this thing up. And everyone said, yeah, why not? So we had 300 people there so they actually got more than what they paid for. T.K. from ToutApp, still good friend of mine, now he’s a VP over at Marketo because they got acquired and, he still says that was the best money he’s ever spent on marketing because everybody thought it was a ToutApp event. We gave them the marquee sponsorship. So it was like Sales Hacker conference presented by ToutApp – in hindsight, should’ve left that part out because for probably a year after that, people thought it was a ToutApp event, but he got a lot of bang for his buck on it and it ran.

The first event took me four weeks worth of work, just one person, just me, and $60 grand in profit. And I was like, “oh, there is a business here.”

Sergei: What was the work that went into that month? How did you get those first hundred people?

Max: Yeah. So because there weren’t a lot of sales conferences at the time or the sales conferences that were around rubbed people the wrong way, it was really easy to get people to rally around this. Plus I had some really amazing speakers on board, and it was the first one that was like dedicated to sales technology, which was this emerging part of sales. You know, everybody really wanted to learn how to leverage things like hiring talent in the Philippines to their teams, or scraping the web to build massive lists to do outbound emailing.

And I had Aaron Ross keynote, which was just a hail mary that I threw out there and at the time was like, “Hey, our whole group read your book and we gotta get this out there more, would you want to come keynote this conference?” So we got Aaron and so we had a pretty amazing lineup for first conference. Also at that time, people would share more. Now there’s a sales conference, sales or marketing conference every week, almost all year. It’s ridiculous. At that point, that was it. If you got a sponsor, they’d promote it and they’d be like, “come stop by this booth.” Now, as you know, a vendor has a conference basically every week. So they usually say, “oh, we’re not promoting that we’re going to be at a booth anywhere to our list because we can’t do that every week, can send that around to an entire list.”

Max (29:32): So it was different. It was a different world than what we live in today. And, even for our business now, I mean, we used to run a conference in New York City called Sales Machine with Salesforce, which was a huge partnership for us and still is a big partnership for us, but we’ve moved it over to digital and we’re getting out of that New York conference and just doing one US conference on one UK conference this year because conferences, for companies like ours are just not worth it. There’s too many vendor based conferences now that can lose money and, there’s really nothing we can do from a conference perspective that’s different from theirs because everybody wants to speak.

Sergei (30:12): Cool. So it sounds like it was a lot of organic growth and word of mouth, and people promoting to their own lists. So you didn’t really have to invest anything in marketing that conference. So you mentioned, I believe that you made $60,000 in profit from that first conference. So what happened after that? The conference wraps up. What do you think?

Vadim: is that 60 grand from just sponsors or did you charge attendees?

Max: yes, we charged attendees for tickets to it.

Sergei: So the conference ends the next day. What are you thinking? What’s your next step?

Max (30:42): Yeah, I’m riding a high at that point, because I didn’t know what I was going to do next after Attorney Fee. I knew at that point that I was sick of making other people rich and I had made two sets of founders a lot of money. And you know, the whole myth about getting equity. It’s like you’re not gonna make much – you gotta be founder. I’m sure my Udemy stock one day might be worth something, but that topic is for another podcast. But at that point I was like, “all right, if I do this for another year, I’ll have a pretty amazing network. I’ll learn a ton from people I usually wouldn’t have access to.” So you know, one of the guys, for example, was Mark Roberge who was the CRO at Hubspot at the time, and he had just wrote Sales Acceleration Formula and we got him to keynote at one of our events and it was amazing because now that I had something of value to a lot of these people, here I am sitting in the same room as Jason Lemkin who just sold his company for $100,000,000 dollars.

And, you know, this isn’t where I was when I was at Udemy. I was heads down, a nobody in tech that was just getting started. And very quickly I went from that to starting to develop a network with some pretty legit people in the space. So I said, “OK, um, let’s try to do this in New York.” So I did the first event in the fall and I was going to New York the following spring. So it was five months out. I had some runway from the money I’d made previously and from the conference, so I was like, “all right, in the meantime, I could do a little consulting here and there for some companies and figure out if there’s anywhere I want to go full time as a co-founder, or a VP of Sales with an equity hit or something like that.

Max (32:32): And nothing really came up that I was like, “OK, I gotta do this.” So I ran the conference in New York – same thing, I think it took me like six weeks and I made $50k in profit and it was like, “all right, there’s a business here, I can do this again. I can keep these going.”

We also started with our meetups. Then those were making like five to seven thousand per meetup, so there was money coming in and I knew there was a business there. But the best thing was that I knew I was building a network and it’s a long-term asset. So if anytime I want to get out of this, I can go get aquihired into a big company or join an interesting startup that raised a lot of money and I’ll carry my network with me and maybe I’ll get a signing bonus for bringing in Sales Hacker or something else, or I just keep running this thing and maybe start a fund.

Maybe I do a roll-up, maybe we build technology into it – there was a lot of different directions I can go in. So it was pretty exciting and then it kinda just snowballed from there.

In 2014, I guess a year later, Jason Lemkin approached me from SaaStr and he was like, “Hey, I want to start a conference, can you help?” And I actually responded to the email. I was like, “yeah, we’ll help you promote it.” And he’s like, “no, I need somebody to actually help run.” It was like, “OK, ummm” – so we actually negotiated a 50/50 profit share on that and I was like,
“he’s got a much bigger network than I do – this is awesome.” He was really passionate about the SaaS space, so we helped them with the first SaaStr Annual, and now he’s doing 15,000 people a year at that conference.

Max (34:08): So we ran the first two events, a from there it opened up a lot of doors for me since, – I wrote the book Hacking Sales, sold it to Wiley, have Career Hacking For Millennials coming out next week. So it just set me off on this interesting journey. But, I don’t know, I never, not at one point looking back on it, was it anything premeditated. I just knew that it was what I’m going to do – we’re gonna keep our heads down and focus on the day to day, getting better every day. And then doors will open for us. And I think we’ve done a lot of things right and we’ve definitely done a lot of things wrong, but nothing that’s sunk us.

Vadim: It’s a really great outlook – when you’re considering entrepreneurship or even just doing, creating anything, really investing your own personal time into something where you don’t really necessarily know if it’s going to reap the dividends and results. It’s much better if you go into it with no expectations. I mean obviously if you’re building a business, there’s certain goals you need to reach. But if you go into it without expectation and understand that, by making things happen out of nothing, by organically creating things – to your point, building relationships, which obviously then came back and add benefits and value and kind of set you off in different directions that you could never predict. Things will sort of bubble up and opportunities will come.

Max (35:26): I remember thinking it was funny – for the first conference, InsideView gave us a $10,000 sponsorship and they were a big company at the time. They raised a hundred million dollars, like Series D – and so I sold them a sponsorship and they said “who do we make the check out to?” And I thought – shit, I gotta get an LLC, like I can’t have them cut a personal check to me. So I went to Legal Zoom. I got a, I think it was called Startup Sales LLC. I didn’t know if it was going to be Sales Hacker. I didn’t know if this was going to be part of the consultancy or whatever I was going to do. Startup Sales LLC was the first step, then I went to the bank, opened a bank account and I was able to accept that check.

I remember thinking like, “oh, this is an interesting business because every ticket I sell is like my money. This is how I make money.” So, all right. We just sold a ticket on eventbrite. I sold three tickets on a Saturday one time and I was at the Cowboys/Broncos game, and in the same weekend, Arizona State, which is my Alma Mater, was playing Notre Dame. So I went down with a couple of my college friends for the weekend. This was right before the first conference – maybe two weeks before the first conference, so I think I sold like three tickets on Saturday and three tickets on Sunday and I was down there getting drunk watching football and I made, you know, $1,800 or something like that. I remember thinking like, this is a pretty cool business.

I like this – it’s something that’s somewhat passive, but at the same time I get paid for the work that I put in instead of, you know, a standard salary at a company where it’s like, you can hustle all you want but this is what you’re making. I felt like I had control. It was the first time I had felt like I had built something where I have a full control over what I was going to make. It was coming directly to me. And, you know, I remember scrambling in the last couple of days there to find a last minute sponsor because it was the same thing if I closed a sponsor and I had room for them and we set them up at the event that’s, you know, $1,500 to $2,500 to $5,000 that came directly to me. So I closed like a $3,500 sponsor at the last minute. That was fantastic. That’s what I used to make in a month, you know, when I first started at Udemy and now I can get that in the last minute on a sponsorship for a conference. Like it just mentally opened a lot of doors for me in my thinking of, of being like, wow, there’s something here and I can control it. I really liked that.

Vadim (37:52): I’m sure that gave you a lot of confidence and clearly you’ve been making things happen. And, basically what started as a conference is now a whole media company. And to me it seems like you’re positioned for a lot more growth as well as the space still has a lot of potential. But can you talk us through maybe one of the scariest moments in your entrepreneurial journey where you thought, “oh shit”, because that happens all the time, right? Where maybe everything will go wrong.

Max: There’s a lot – where to even begin. Yeah, I mean there’s probably stuff that I don’t want to share on a podcast, but like one of the biggest was first realizing that nobody is irreplaceable. So I had an employee early on at Sales Hacker that did a lot of the heavy lifting on things. And I let them do a little more than I than I should have – I let them get away with a little more than I should’ve. But I was so scared to do anything about it because I was like, what do we do after them? Like, I don’t even know what I would do. I’d be screwed. And looking back on it, you know, obviously after we parted ways, I realized like, Holy Shit, I didn’t really need that person. I could replace that person.

Vadim: The good thing is that a lot of times, you know, especially when you’re working, it’s your baby, and when somebody leaves or whatever it is, it seems really, really bad. It might be a little bit sustained and the feeling is stuck with you for awhile, but eventually you’ll figure it out. I mean, you have to figure it out if you want to keep the business going, and you may even realize that you built it up to a point where it’s much worse in your head than it really is.

Max: Yeah. Um, when you first start working on your own company or first are working in start-ups, I saw like a really good graph. The amount of time you’re working on something was on the X axis. And then on the Y axis it was the highs and lows. And so when you first start, the lows are really low and the highs are really high. But as time goes on and you’ve done it more things narrow and then eventually you don’t care. So any low is like, “oh, been there before”, I’m talking to Matt about this in a week so I’m not going to be mad about it right now. And even the highs – like just a milestone, on to the next thing. I’m in this weird place right now where my girlfriend is always like, “you’re launching your second book next week. Like, celebrate, let’s do something that’s amazing.” And I’m just like, that’s not interesting to me.

The book’s got to sell 3,000 copies in the first week, and she says “then will you celebrate?” It’s like, no, because then I’ll want it to sell five. And you’re just like always striving for something or it’s always the next thing. Like even if somebody were to come and give me the amount of money I want to acquire Sales Hacker, you know, at some point it’s like cool. Like I’m onto the next thing. How are we going to integrate it? What are we going to do? Like this is fun. It’s a journey. I’ve kind of lost track of hoping for some kind of destination or wishing for some destination and I’m just enjoying the journey, but it took a while to figure that out. It took a lot of ups and downs to figure that out and I think a lot of entrepreneurs want to be on track, – they have a certain destination in their mind, a certain level that they want to be at professionally, certain amount that they want in their bank account and I think that’s a good thing because a lot of times that’s what motivates you to get started, but if you’re not enjoying the work day to day, if you’re not enjoying actually tackling the challenges, which is why we talk about sometimes it’s not easy to think of the right idea, but think of that business that you actually want to run day to day over, let’s say a specific huge milestone because it’s more so about that day to day and you need to enjoy it if you’re going to push through the difficult times and to be able to see opportunities where other people don’t see them and you won’t unless you’re sort of optimistic about the work that you’re doing day to day.

I need to strike a balance. I mean, I agree with my girlfriend that I need to start cherishing some of the good times a little more and I got to figure out how to do that after a few years of becoming numb to emotions on a lot of these things, which has been a good thing. Because, if you let the negative stuff get to you, it can completely consume you and your business. And you also don’t want to get into the Crunchbase or Tech Crunch world where you’re like, “well, I thought I was doing good, but that guy that started his company at the same time as mine just raised a million dollars, and so I guess I’m not really doing that good.” And then you start comparing yourself to other people or you don’t want to get into that either.

Max (42:46): So, for a long time I’ve tried to stay away from that, and now I see it and it’s like good for them. Like I have a network of really successful people that have come up kind of around the same time that I started coming up. And it’s inspiring. I’m a competitive person, but I need to be competitive with myself and doing better every year than the last and not competitive with other people. Those are variables I can control, and it took awhile to figure that out.

Vadim (43:20): Yeah. Big, big takeaway from this episode for me personally is that anyone that’s just starting out, it’s important to just go out there and try different things and start different businesses start different, let’s say even Meetups, which is what this essentially grew out of, without necessarily having that specific destination in mind and being open to things happening that you can’t necessarily foresee. The more you start, the more opportunities you create for yourself and the more you learn what not to do for the next time.

So don’t try to plan the perfect outcome. Just take it as it comes and continue building on yourself and hopefully that will turn into a business. Certainly don’t, as you said, worry about what other people are doing because you’re not aware of the problems that they have anyways. And the things that we see online and publicly posted are probably 10% of the story at most. So I would say I agree with you. Embrace the numbness because that’s the thick skin that everybody talks about. It helps you get through the terrible times, but also I think it’s okay even to be numb sometimes on the positive stuff because that just means you’re focused on the next thing.

And you have a ton of stuff going on. You have a couple of companies now. You have several books – we’re going to continue to follow your path. It’s been really exciting. We’ve actually been aware of you for a while, kind of on the side, and you were always offering value through your content, which is why we’re so excited to have you on the podcast. So thanks a lot for coming by, Max!

Max: Yeah! Thanks for having me.

Show Notes

  • 2:44 Deciding to start a bike sharing company in college
  • 4:00 Starting a social media management company and moving to Costa Rica
  • 7:10 Getting a dream job at Udemy and becoming an expert sales professional
  • 8:10 Why now anyone can be a freelancer and work for themselves
  • 9:20 Max's advice for starting your own Instragram consultancy
  • 14:43 Self-educating and learning how to sell to anyone
  • 17:50 The importance in believing in the product that you're selling
  • 20:00 How to create content that does not become obsolete
  • 23:50 The early stages of Sales Hacker, and how the idea of a conference came about
  • 26:43 How Max got his first major sponsors
  • 28:00 How 4 weeks worth of work resulted in $60k in profit
  • 28:40 Getting Aaron Ross to keynote his event
  • 33:33 Why Jason Lemkin asked Max to help him run his first SaaStr conference
  • 38:08 Max's scariest entrepreneurial moment
  • 40:20 Becoming a best selling author
  • 43:25 The importance of taking action and embracing the highs and lows
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