What I learned from interviewing 22 successful entrepreneurs

I believe it was back in 2012 when I started interviewing people for my blog. I did the first interview for my personal blog, here on duskic.com. Then on my business blog, over at whoapi.com/blog. After that, I started a new website webmaster.ninja and posted a few interviews there as well. It was a humbling experience because some of these people are multimillionaires, some are true rock-stars in their industries, and some are able to give you that one simple piece of advice that magically doubles your income… or something similar.

Since it’s been a few years, I thought it would be a good idea to create a condensed post with a list, if for no other reason, so that I can reflect and see what advice I picked up over the years. I am sure you are going to be able to find a few tips yourself.

Joel Gascoigne

I first reached out to Joel via Twitter, and he was super nice about it. This was back in 2012 before I pitched 500 Startups and found out I am going to live in Silicon Valley for 4 months. Turns out Joel and Leo Widrich were also there at the time, and I ended up meeting Joel in person! If you read the interview with Joel, you can see right in the title that he is focused on customer happiness. After the interview Joel also became huge on transparency, so now (and for the last few years) Buffer’s numbers are public!

Focus on customer happiness!

–Joel Gascoigne

Joel Gascoigne is the Founder and CEO of Buffer, a social media app that helps you with scheduling your posts. According to Baremetrics, they are making around $1.54M per month in revenue every month.

Sasa Sarunic

I met Sasa at a local meetup when he was with agency Five and startup Shoutem. Companies he co-founded and helped build together with Viktor Marohnic but left a few years later. What I learned from Sasa’s interview was that he had years of experience before making any success and that they started hiring people only when it started to hurt. (Meaning they couldn’t do the work themselves, and they could afford some help).

Hire for growth!

–Sasa Sarunic

Sasa Sarunic is the CEO of Five by five since September 2013 (a company he started after leaving agency Five) and a co-founder at Agent Cash (now Floe). According to Crunchbase, Techstars is an investor with Agent Cash.

Jason Mendelson

I reached out to mr. Mendelson when I was doing investor outreach, and wanted to get in touch with Foundry Group. Among many high-profile investments like Moz, they invested in technical and API companies such as Full Contact (I interviewed their CEO Bart Lorang as well, check below). More importantly, their team venture partners (like Brad Feld) are very tech savvy. Jason’t advice stood the testament of time.

Having self-awareness to be able to constantly monitor one’s own performance is key. Aside from that, have a maniacal focus on the product and customer is a must. Release product often and be deep into analytical thinking to gauge success.Click To Tweet

Jason Mendelson is a co-founder and a partner at Foundry Group an early-stage technology venture capital firm. They invested in Moz, Full Contact, Yesware and other.

Ben Coe

Before Jason, I interviewed Ben Coe. I heard about his startup attachments.me from one of our clients’ domain registry .me. I reached out and the result was that interview. I am sad to report that his startup went under, (Foundry Group and Jason invested around $2M according to Ben’s LinkedIn profile), but these things do happen. Even successful startups miss several near death situations.

Just like Sasa Sarunic, Ben told me that even if he had a successful exit, he would have fun a little bit, and then start another company. Ben is currently a systems analyst at Npm, Inc.

That’s about it as far as interviews on duskic.com go. These were mostly startup related because I was trying to figure out how to reach out to investors and what it was like to run a VC backed startup. I haven’t mentioned it here, Sasa’s startup at the time (Shoutem) had 1 million euro backing from a local VC fond – RSG Capital (now operating under the name South Central Ventures).

Moving on to a bit different set of interviews. These were published on WhoAPI’s blog, and were mostly around successful domain name investors and domain registrars.

Mike Mann

I interviewed Mike Mann back in May 2012, which was about a month after he became known to the world as a domain investor who registered 14,962 domain names in a single day. At the time of the interview, Mr. Mann said that he owned 300,000 domain names like seo.com, software.com, phone.com, DomainMarket.com, PRMarketing.com, PurePPC.com. His advice was to stay focused on the .com TLD and forget the new domain extensions.

.com is king, people will be disappointed with all other tlds.

Mike Mann

Mike Mann is the author of Make Millions and Make Change. Mike is also the founder of several successful, active, for-profit corporations. Three of these corporations were listed among the 2012 Inc 500 fastest growing companies in America: Phone.com, DomainMarket.com and SEO.com.

Frank Schilling

I’ve met Frank Schilling in person while I was at the ICANN 44 meeting in Prague. Very rarely have I had the opportunity to meet someone who has achieved so much, yet you have a feeling true greatness is yet to come. Like Mike Mann, he owns a ton of domain names and a patent in domain industry. Speaking of patents in domain industry, Paul Stahura and Pinkard Brand also have them (check below). The second time we talked he gave a glimpse of the new domain extension wave. Preety much the exact opposite of Mike Mann’s focus on the .com.

Frank Schilling is the founder of Uniregistry and DomainNameSales.com. The Namepros domaining community agrees that at one point he owned the largest domain name portfolio and don’t be surprised to see his company sold $12 million USD worth of domain names.

Rick Schwartz

If you think that $12 million dollars worth of domain names is a lot, check out Mr. Schwartz’s portfolio self-evaluation + past deal numbers. His biggest advice in an interview with me was not to quit your day job until it interferes with your domain investing earning capability. As for as domain investing goes, he said to buy domain names that are valued at $1,000, and sell those for $10,000. After that you just rinse and repeat until you get better at it.

If you think that buying a domain name for $1,000 only to sell the exact same domain name for $10,000 is easier said then done, you would probably be right. Hard, but not impossible.

Here’s how Rick Schwartz did it himself. He bought the domain name porno.com for $42,000 in 1997 and sold it in 2015 for $8.88 million. In the 18 years that he owned the domain name, it earned approximately $15 million. In 2003, he sold men.com for $1.3 million (purchased for $15,000). In 2008, he sold Candy.com for $3 million, plus a 12.5% equity stake, to a candy company that had been in business for 35 years. Lastly, in 2004, he sold iReport.com to CNN for $750,000, but then again, at the moment this domain name is not even resolving. Seems to me like someone wasted $750,000. HA! Unless they sell it at a 10X multimple, as Rick Schwartz advises.

Rob Grant

Mr Grant’s story is a classic rag to riches story. Ok, maybe not exactly “rags”, since he had a nice paying job on Madison Avenue. But he wasn’t having anything near of success with his domain names. He was definitely one of the pioneers, and during his interview with me, he shared a few nuggets of wisdom. One thing, in particular, stood out. You should never think you are at the top. The moment you do, you are done. This is especially true in the internet space. No other industry changes as rapidly and without warning as technology.

You should never think you are at the top. The moment you do, you are done. This is especially true in the internet space. No other industry changes as rapidly and without warning as technology. -- Rob GrantClick To Tweet

Rob Grant currently owns more than 8000 domain names and has had some success with selling them and building websites. In his spare time, he is attending his daughter’s (Lana Del Rey) concerts.

Paul Stahura

Mr Stahura apart from being kind to do the interview helped me with business advice on several occasions. He is definitely a pioneer who had huge success in the domain industry on more than one occasion. As you can see from the interview, he has several patents and built one of the largest domain registrars at the time (eNom). Once eNom was making tens of millions of dollars, he sold it to Demand Media. Paul’s advice was focused on new gTLDs and how legitimate domain investors can make money by providing value to the marketplace. He confirmed how .com will still probably stay on top, but new domain extensions will have a place under the sun.

Paul Stahura is currently executive chairman and co-founder at Donuts Inc after leaving the CEO position in January 2017. In November 2017 Donuts Inc. ranked fastest-growing company in North America on Deloitte’s 2017 Technology Fast 500, followed by an acquisition in September 2018 by private equity group Abry Partners.

After Paul Stahura I took a little break from interviews, but then returned strong with some very high-profile interviews that I published in my ebook.

Mitch Wainer

Mr John Ives (Managing director at Tahoma Ventures) introduced me to Ben Uretsky and Digital Ocean. The reason why I am saying this is because I ended up working with Digital Ocean on several occasions, and although I didn’t get to interview Ben Uretsky, I met Mitch and we spoke on several occasions! Sidenote, there’s a great lecture by Mitch on growing your startup. You should definitely check it out. It’s very hard to single out one good advice Mitch gave me! But I think we can all learn from their stellar growth (from 2000 clients in January, to nearly 150 000 in December 2013) since they announced their $5 SSD VPS plans on Techcrunch. Great product, offered at an amazing price at the right time, and voila!

Mitch Wainer joined DigitalOcean as co-founder and Head of Marketing in 2012 and left after 6 years. He is currently Chief Marketing Officer at Clubhouse and advisor at Flybridge Capital Partners.

Bart Lorang

Bart was another perfect interview for my eBook since Full Contact, like DigitalOcean, fundraised a lot. Back in 2015 when I interviewed Bart, they were handling over a billion contacts, and they’ve raised around $20 million in funding. The thing that stood out most during the interview was his deep care for his employees! They call it the “Paid, Paid Vacation” and their blog post explaining the concept went viral.

Speaking of viral blog posts, the other one that Bart mentioned during the interview was his “The Story of 126 No’s and 1 Big Yes“. Hint, watch Bart’s video for Techstars application. As far as the blog post goes, I highly recommend it since it’s their entire journey from a basement (hint again, check the basement in the video) to getting an investment from Brad Feld (Foundry Group, the same person I mentioned earlier when I talk about interviewing Jason Mendelson).

Here’s the video before Bart decides to pull it off the Internet.

Even after this video, Bart Lorang is still the Co-founder and CEO at Full Contact. According to Bart’s interview with Nathan Latka back in December 2016 Full Contact has 220 employees, revenues of $12M in 2016, 50K+ customers and have raised $50 million in funding.

Isaac Saldana

Isaac invested a little bit of money in my company WhoAPI back in 2013 when Dave McClure introduced us over email. I interview Isaac for my ebook, but after Sendgrid had an IPO I really wanted to publish the interview and share the interview for free with everyone. After a short update, the interview went live. Isaac reveals how he was facing a challenge while working on something, and he decided to face it head on! After having some initial success, he went on, and on. That translated into him becoming mission driven. Other people noticed, clients, starting using this product, and investors started investing in the company. The rest is history.

Isaac is currently acting as the co-founder and CEO at Joy Labs. Sendgrid, the company he co-founded sends more than 37 billion transactional emails it was acquired by Twilio after going IPO. Earlier, Sendgrid raised more than $80 million in funding.

David S. Rose

In his TED talk, David S. Rose introduced himself as someone who both raised and supervised investments of tens of millions of dollars. In the interview (which is published in my ebook), I asked him if there was anything that stuck out as an obvious commonality among all those deals. Here’s what he had to say: “If there is a commonality among the various companies in which I’ve invested—aside from the founder having impeccable integrity, which for me is the number one criterion—I think it is a sense of entrepreneurial optimism, passion, and vision combined with a sense of reality.”

If there is a commonality among the various companies in which I’ve invested I think it is a sense of entrepreneurial optimism, passion, and vision combined with a sense of reality. David S. RoseClick To Tweet

David S. Rose has been described as “New York’s Archangel” by Forbes. He is a serial entrepreneur, Inc 500 CEO, active angel investor, and CEO of Gust, the SaaS platform powering over 600,000 startups and 75,000 early-stage investors. He’s the NYT bestselling author of “Angel Investing” and “The Startup Checklist.”

Patrick Ambron

I reached out to Patrick at the time when my fiance and I tried to start a project that would offer unique illustrations on a company mug. The project ended up to be a disaster, but the interview with Patrick turned out to be just fine. The biggest message I got from that interview, and the research I did before the interview, was that if you truly solve a big problem that people care about, they are going to come by the thousands. I know my vanity kicks in when my name appears on Google, and I want only good and respectable results. Patrick’s company BrandYourself helps non-techincal users achieve just that.

I interviewed Patrick back in 2013 before he pitched his startup on Shark Tank where Canadian-Croatian Robert Herjavec offered $ 2 million for 25%. Patrick turned down the offer. They now have more than 100 employees. Back in 2016 BrandYourself reported to have raised $ 6 million so far, and made $4.2 million in revenue for 2015. Nice progress since 60,000 signups in 60 hours (confirmed during my interview).

Daniel Greenberg

Riding the wave of branding (personal and corporate) I reached out to Daniel regarding the company mugs (yes, the same project that was a disaster). To this day, I still find myself drinking coffee from those mugs, and I am happy that we were able to create those mugs for them. As far as the interview goes, I still remember the shocking story where an African medical insurance company allowed a domain name linked to the management of its domain names to lapse and be deleted!

Daniel is the owner and managing director of Lexsynergy, a company that specializes in online brand protection and domain management. They have offices in London, Vienna and Johannesburg, with clients from around the world.

Pinkard Alan “Pinky” Brand

I’ve interviewed Mr. Brand years after I met him during the World Hosting Days (now called Cloudfest). I finally decided to ask him to join me on a Skype call where we discussed: domain name extensions, China, Marc Ostrofsky. The information that just blew my mind was that: “Keep in mind that China’s 618 million Internet users are comprised of 28% rural users (177 million) with 81% of those users (500 million) going online via smartphones and tablets. And still, Internet penetration has reached only 46% of China’s 1.3 billion. Also, only 10 million of those 1.3 billion speak English! That’s less than 1%!

Combining my thoughts from Daniel Greenberg’s interview (growth in Africa) and this interview (growth in China) you get the feeling the Internet will change a lot in the coming years! Pinkard Brand is currently acting as the Senior Vice President of Marketing and Sales at RegistryOffice.

Tomislav Bilic

Tomislav’s story could be very interesting to domain investors. His company (around $2 million in reported revenue for 2016 with 50 employees in 2018) has remained on their .net domain name since the beginning! Matter of fact, one of their clients (partners, or employees, I am not sure) bought and gave them the inchoo.com domain name as a gift! Obviously, Tomislav was obsessed about the right things, and the dreaded .net domain extension hasn’t stopped him on his path of success. On contrary, it is still their main domain name!

Marko Kovac

Speaking of Croatians and successful .net domain names salespod.net comes to mind! I think I met Marko Kovac, CEO & Co-Founder of Repsly during the GOAP event in Zagreb. The reason why I reached out to him for an interview was that they had just finished a rebrand from salespod.net into Repsly.com. Although this wasn’t exactly a full-blown interview (I topped it off with “12 things to watch for when picking a new name.”) we did have a great talk, and I think one can learn a lot from their example and early mistake of choosing the domain name salespod.net.

Repsly made around $5 million in revenue back in 2017, and counts around 60 people in their team and raised more than $4.8 million to date.

 

Rimac, Repsply, WhoAPI - photo by Marina Filipovic Marinshe, source Netokracija

Rimac, Repsly, WhoAPI – cover photo by Marina Filipovic Marinshe, source Netokracija

After those interviews, I more or less took a break from interviewing and posting my findings. I eventually got around to it when I started posting content intensively on webmaster.ninja. My idea there is to get advice from experts in various fields on how to become a true Ninja Webmaster. You would then by definition need advice on web hosting, domain names, SEO, and so on. I started with advice from:

Glen Allsopp

Glen shared his favourite SEO tools, thoughts on latest Google search algorithm update and the reasons on why he got into this industry in the first place. Money was the initial factor, but now when he is maybe even set for life, he is giving away super-duper SEO advice for free. These are so good it will make your head spin! Advice that stuck with me the most (during the interview, (if I put aside advice on his awesome website) is that I should relax if I get a negative comment.

I’ve had blog posts where I get 300+ comments of total praise, and then one or two which are just…harsh. Of course, being the slightly flawed humans that we are, it tends to be that those 300 positive comments quickly go out of the window and it must be the two negative ones which we believe to be true. I see this happen on a lot of blogs. Authors ignore a lot of the praise but always rush in to defend themselves against the critics.

Tim Soulo

Since I was using Ahrefs for years, (and Glen listed Ahrefs as one of his favourite SEO tools), I just had to interview someone from Ahrefs. I reached out to Tim Soulo a while back after taking a course he created, called Blogging For Business. It was absolutely free on the day of the launch, and it seemed to good of an opportunity to miss. Tim is their marketing director and he spends a lot of his time into creating content.

His advice on how to create content that converts readers is just amazing, but also too long to fit here. Hop here to read the interview with Tim Soulo of Ahrefs!

According to our data, almost 75% of pages that rank in top10 for a given keyword doesn’t have even a single mention of that exact-match keyword anywhere on the page.Click To Tweet

Spencer Haws

My car is one of those “college on wheels” type of vehicles. Me and my fiance mostly listen to audio books or podcasts. Niche Pursuits is one of them. Among many podcasts, some have the power to help you change your life. Again, Niche Pursuits fits the category. So who is Spencer and why we should listen to his podcast?

I think I am not far when I say that Spencer made his first million when he sold Long Tail Pro. A software that helps SEO experts find keywords that are high in traffic, but low in competition. An SEO tactic he practically invented. For some people, that’s where the story would start and end. However, Spencer made a lot of money with his Amazon FBA business, before he sold it for nearly half a million dollars.

Here’s the kicker, he did all that without any outside funding, and AFTER he created a small website empire. If you imagine a beast working in a cave 24/7, you would miss by light year. Spencer is a loving father of four and that’s the first thing he uses to describe himself in his about page. Mindblowing!

His #1 advice from the interview, I keep repeating to others is:

The ideal niche can be found is at the intersection of these 3 things: low competition keywords, money in the niche, and your interests.Click To Tweet

Michael Cyger

Last but certainly not the least, was the interview I did with Michael Cyger. We talked just a couple months ago about picking the very best domain name for your new website. Michael started a very popular domaining blog and a podcast DomainSherpa.com back in 2010, and most people know him from there. Recently he started DNAcademy which I attended and was able to learn a few domain investing tricks myself!

These companies are trading the up-front cost of buying a premium domain name for years of hidden costs, not just from a lack of productivity in communications but also from being associated with a weak brand. Click To Tweet

For those of you who missed it, Michael is essentially talking about opportunity cost. And if we are to trust Alan Dunn, the world is running out of good domain names.

Conclusion

Wow! And we are done! I hope you found some good advice within those lines, and that you can implement them tomorrow at the latest. You have the night to think it over. Please share the post with someone who is currently strugling with their business.

ABOUT THE AUTHOR
Entrepreneur for more than a decade in the hosting and domain industry. Started and sold a small web hosting business. 500 Startups and StartLabs alumni. I am the CEO of WhoAPI. I also own 50 small and passive websites in various niches.
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