The path to doing what you love is not always straight forward, and sometimes the hardest part of becoming an entrepreneur is figuring out what you don’t know and trying to fill those gaps in knowledge as quickly as possible. Before he became an accomplished author, successful entrepreneur, and popular podcast host, Steve Glaveski, author of Employee to Entrepreneur, was there himself, which is why he decided to write a book that provides a blueprint for people that want to be freed from the corporate world and learn how to become creators and entrepreneurs.
In this interview Steve describes how he went from being a corporate employee that didn’t feel purpose in his life to starting multiple successful businesses and building a life where he can create impact for the world. He provides highly tactical and actionable advice describing exactly how he built his businesses, from how he scheduled hundreds of meetings with prospective customers and leveraged press to raise money, to the actual tools that he uses to automate tasks and accomplish all of his goals.
We also discuss what Steve did to grow his team at his current company, Collective Campus, a corporate innovation and startup accelerator, and why he thinks it’s so important to outsource certain parts of your job as quickly as possible to focus on high value activities like business development and strategy to accelerate your business growth.
1:10 Steve, you’ve done a lot of cool things and built several businesses, but at some point you were just an employee somewhere. What first started your entrepreneurial journey?
1:36 Was working at a big consulting firm helping big companies comply with the SEC. I would make a bunch of recommendations and rarely see them implemented. So the work was quite unfulfilling, despite a 6 figure salary, perks, etc.
2:30 But I listened to what Steve Jobs said which is if you wake up enough mornings not wanting to do what you have to do that day, you should change what you’re doing. In the end I had enough of this.
3:16 It started with a platform called HotDesk which was sort of an Airbnb for office space, taking advantage of empty office seats.
3:40 While you were still working, how long did it take you to get from idea to some concrete output and what was your first step to making it a reality?
4:04 First thing I did was find a place to put up a free advertisement to get meetings with a bunch of businesses and entrepreneurs to get advice from them. The feedback I got from them was that it was a good idea.
4:55 Then I went on Upwork, hired an engineer and with an Airbnb script I downloaded, we made a prototype for HotDesk for about $2,000 total.
5:10 Then I needed to get the word out so I emailed 100 journalists a press release I drafted. Only one journalist got back to me but it was one of the biggest newspapers in the country.
6:16 From that article I received $150K in seed funding from investors who reached out to me. 3 months later I was full-time.
6:50 Vadim – What I love about this story is that you were just willing to try things even if you didn’t know how to do them, which is so critical to being an entrepreneur.
7:17 Steve – absolutely. Most people from the corporate world are used to just planning to the n’th degree. But when you take the leap, you just have to be okay with ambiguity.
7:57 Take the smallest possible steps to have the biggest learnings you need to take the next step.
8:09 Sergei – How long did it take to generate revenue with that idea?
8:15 Steve – I learned that building a 2 sided marketplace is 10 times harder than just a one sided business. You need to sell to both supply and demand side.
8:44 Getting to 12,000 office spaces across Asia-Pacific – supply side, was easy. With Demand side, you can make the initial introduction and get a commission, but the problem is if someone liked the space they would negotiate directly with the owner to stay. So even though we got to revenue in less than 6 months, retention was hard.
9:30 I worked on HotDesk for a few years, and we got it to $10K monthly revenue, but after a while I wasn’t believing in what we were doing. I didn’t want to be a glorified real estate agent. You need to align with the purpose in the long term.
10:30 Sergei – there is a lot of value to going all in on something because you learned so much from it. But for a lot of people, they don’t even know what idea they should pursue or jump all in on. Having the benefit of hindsight with this idea, how did you figure out what to do for your next thing?
11:20 Steve – you’re absolutely right, I learned so much in my first year across sales, marketing, persuasion, product development, fundraising, more than I learned in corporate in 5 years. So there’s no substitute.
12:12 For my next business, it was serendipity. I was working out of a space where General Assembly (the education company) was, and they left. We had 2 vacant classrooms and I decided I wanted to use it to start bringing entrepreneurial frameworks to corporations, including lean-startup methodologies. I pitched the guy that ran this space and we started hosting events.
13:42 We spent $100 on LinkedIn ads to get people to the first event. Got 60 RSVPs, only 3 people showed up but we started to build a client list and eventually booked our first big client, which took 6 months. Which gave us the social proof to keep doing it.
14:00 This is really fulfilling for me because I get to help people who are in corporate roles like me and give them more entrepreneurial freedom and creativity in their roles.
15:10 Before we booked our first client I had over 300, 30 minute, meetings with HR managers, innovation managers, etc. to learn what pain points they had that were in common. I wanted to base my decision on patterns and then pitch directly based on their struggles.
15:40 We were running a kids entrepreneurship program called Lemonade Stand during the summers only, and one of the kid’s mom was a head of innovation at a major law firm. She loved Lemonade Stand and wanted to bring something similar to her company.
16:30 We were able to use that client to get 10 more big law firms as clients.
16:50 Sergei – getting 300 meetings in and of itself is hard. How did you do that?
17:06 Steve – We used a tool called MixMax to send mass emails that we found with a tool called RelateIQ that scraped LinkedIn. This way we would email 200-300 people per month and follow up, and test different job titles and companies and eventually reached out to 2,000 people to get those 300 meetings.
17:50 Some people aren’t comfortable with the cold email approach, but when you’re starting out you need to give yourself as many chances as possible to succeed because you don’t have a lot of time.
18:25 You need to get comfortable with it and realize that you’re reaching out to that person because you’re trying to make their lives better and provide value.
19:07 One of the chapters in my book, Employee to Entrepreneur, is called 10X Your Productivity. It talks about how to effectively prioritize to figure out what you shouldn’t do. Only do the things that add value. I also talk about automation, something that’s rudimentary or a step by step task. You shouldn’t do it. Time is your most precious commodity.
19:45 You shouldn’t be doing something that a computer can do for you for $10 a month. If you can’t automate it, outsource it. As an entrepreneur you shouldn’t waste your time with $10/hour tasks.
20:10 That frees you up to focus on high value task. That requires self awareness and reflection to determine how you actually spend your time.
20:54 Vadim – you had a great article on Medium called “How to be half as busy and twice as productive”
What were the steps you actually took to find good talent when you were outsourcing?
21:15 Steve – I started off reading about it to know the right way of outsourcing, but only enough to start executing.
22:23 The main thing to know about outsourcing is to be super specific with your instructions, with step by step details, screenshots etc.
24:00 Sergei – Since you know about starting businesses while still employed, how do you manage having a full time job and finding time to work on your own business and how do you know what to focus on?
24:33 Steve – for me I was just focusing on my free time to testing my key assumptions. When you’re deciding what to test, figure out how certain or uncertain you are that some assumptions are true or not, and test the ones you’re most uncertain about that are the most critical to the business.
25:10 For Uber, the first assumption they tested is whether people would have the trust to jump into a car with a stranger, not testing whether they could build this platform to connect drivers with riders.
25:55 Most entrepreneurs, if somethings not working they think it’s a marketing problem, but more often than that it’s a value proposition problem, and they haven’t done the work they needed to figure out what the right customer segment is and the right problem to solve.
26:38 Another thing founders can do if they can’t just go full time on a venture yet, is leverage their corporate experience to get a 2 day / week contract gig to just cover basic expenses and remove the stress. That’s what I did.
27:30 Vadim – the other thing I wanted to ask you is, since you’re a writer (employeetoentrepreneur.io) what’s your process mastering the focus to write, but then also following through with effective marketing of your writing because there’s no guarantee people will buy a book, and you’ve already been an Amazon Best Seller.
28:47 Steve – in writing any content, say even blog posts or articles, you have to divorce yourself from the engagement numbers. I’ve written many articles that didn’t get much engagement but I saw that as me consolidating knowledge.
29:10 On the marketing side of things I would also recommend automation. Buffer, Repurpose.io, QuuuPromote etc. to help you expand your reach.
29:58 I also mention relevant influencers in blog posts and then contact them to let them know, and ask them to share if they like it. 1 out of 4 times they do share.
30:18 But you have to be willing to play the long game.
30:42 The reason we got into content is because we’re selling into big organizations, and it helps us build credibility. We can point to articles we’ve written to answer concerns they might have, and show our expertise.
31:10 Then we took our blog content and turned them into industry specific ebooks for example innovation in insurance. Then we would use similar automation from before and email specific insurance related people and share the ebook. Once they downloaded the book, they’re in our mailing list and we start to build a relationship with them over email and through more content.
32:00 Sergei – I have to ask, since you have a lot of entrepreneurship related content, does the question from corporates ever come up that you’re teaching their employees how to be entrepreneurs and eventually leave?
32:27 Steve – it does come up, and what I say is that if your employees are inclined to leave to start their own thing, they’ll do that anyway. But you want to harness the energy while they are here. And if you give them a reason to stay, maybe that’s enough.