The Top Entrepreneurs In Money, Marketing, Business And Life

Chris Guillebeau, a world traveler and writer who helps people get the kick start they need in life. Listen as Nathan asks Chris about the publishing industry’s trade secrets, and how he built a booming career in writing. Famous 5:Favorite Book? – Mountains Beyond MountainsWhat CEO do you follow?— N/AWhat is your favorite online tool?— OmniFocusDo you get 8 hours of sleep?— NoIf you could let your 20 year old self know one thing, what would it be?—You don’t need to have everything figured out, don’t be afraid.\ Time Stamped Show Notes:01:17 – Nathan’s introduction 01:35 – How Chris makes money02:30 – Chris is 3702:38 – An entrepreneur is someone who will work 24 hours a day to avoid working 1 hour a day for someone else03:15 – So many people are out there making a great living for themselves OUTSIDE of silicon valley04:15 – The #1 thing you can do is create something of value05:55 – Relationships are the key to success07:12 – Make sure your book kills in the first few week07:51 – Chris is published through Ra

Ezra Firestone, the Smart Marketer and Co-Founder of BOOM! By Cindy Joseph. Listen as Nathan and Ezra discuss the intricacies of intelligent digital marketing, why a universal sales funnel can work extremely well, and how the relationships you make are often your best tools for success. Time Stamped Show Notes:01:17 – Nathan’s introduction 01:49 – Welcoming Ezra to the show02:11 – Talking about BOOM!02:27 – Fundamentally—they’re selling an idea03:00 – http://www.boombycindyjoseph.com/04:23 – The best-selling item of 201304:43 – Ezra uses a universal sales funnel05:12 – Engage with content and then make an offer 06:00 – No long-form sales page, just the product list07:24 – Different content sells to different people08:04 – Get facetime, build intimacy10:00 – the lifetime value of a customer—historically $12011:00 – Ad purchasing is done manually11:25 – Buying traffic is wide to narrow---work wide to narrow12:00 – See what works, then hit it hard and fast13:00 – eCommerce business doesn’t do as well as informat

Scott Hansbury, CEO of YouStake, a company that gives poker fans the ability to stake their favorite players in real, fully-licensed tournaments. As a 53 year-old entrepreneur and former Sun Microsystems executive, Scott is a goldmine of business insight—listen as he shares those insights with us on today’s show.   Time Stamped Show Notes:01:18 – Nathan’s introduction 01:45 – Welcoming Scott to the show02:00 – Giving up the corporate world02:46 – Talking successful exits03:32 – Mezzanine round of funding04:00 – ARR was $15M when they sold to Sun Microsystems at $400M—during the silly days of the internet ‘99 05:31 – Staying motivated when you’re “Set for life”07:15 – Staking in the poker industry08:19 – Person to Person sponsorship—IRS approved!08:44 – Bootstrapped to launch10:25 – How the betting/staking works11:08 – So far, YouStake has garnered $2.8M stakes and $1.4M pledges12:30 – There are a shitload of poker fans worldwide14:24 – The average stake is $34015:13 -- %5 goes to YouStake and 2.9% goes to fee

Gina Tost, a journalist, author of the book Vida Extra, cofounder for Gin App—one on the Top 100 Start Ups of 2015. Listen as Gina shares insights surrounding her marketplace app and how her company creates organic reach in Barcelona. Famous 5Favorite Book? – Who by Geoff Smart and Randy StreetWhat CEO do you follow?— NoneWhat is your favorite online tool?— Twitter & TweetDeckDo you get 8 hours of sleep?— NoIf you could let your 20 year old self know one thing, what would it be?— Focus on learning everything because you’ll never know when you can use itTime Stamped Show Notes:01:00 – Nathan’s introduction01:48 – Welcoming Gina to the show02:02 – All about Gin App04:20 – Currently working with 350 advertisers and 700 sources06:35 – Annual revenue for 2015 - $750K07:40 – Monthly subscription10:45 – Average invoicing of $1000 monthly11:29 – “We don’t track cost per signup because, nowadays, everything is organic”13:25 – More than 10,000 bloggers made money from the app13:53 – Twitter @Ginapp15:24 – Famous 5

Andrea Loubier, the CEO of Mailbird, a company that is revolutionizing the way online communication is conducted through email reform. Tune-in to hear Andrea talk about abandoning her humdrum corporate life for her exciting entrepreneurial venture based in Silicon Bali. Andrea Loubier is a travel addict, who is obsessed with spicy food, third culture kid who is crazy passionate about improving the unification of online communication...starting with email. As the CEO of Mailbird and one of Southeast Asia leading female thought leaders, Andrea is taking on Outlook from Silicon Bali. Time Stamped Show Notes:01:12 – Nathan’s introduction 01:39 – Welcoming Andrea to the show01:54 – Building the business in Bali02:03 – Mailbird is a Swiss-Army knife for email02:50 – Just hit 1M mailboxes managed03:14 – Close to $500K in AR03:44 – They’ve hit on a solid model05:09 – The Flash-sale pricing structure05:55 – After the banner—20% conversion06:45 – Before the banner—10% conversion07:15 – Mailbird has been around since 20

Nathan speaks with Daniel Brusilovsky and Jason Stein, the co-founders of i-Moji.Daniel Brusilovsky and Jason Stein are two of the co­founders at i­moji, the largest sticker library in the world. Time Stamped Show Notes:01:08 – Nathan’s introduction 01:33 – Welcoming Daniel and Jason to the show01:45 – Six founders of i-Moji02:48 – Do what you’re passionate about03:30 – Jason originally operated at Hotel Tonight03:54 – How they’re making money?—They’re not04:48 – Give users as fast and relevant experience no matter what05:48 – A b2c product06:05 – Left Shark example07:01 – Proactively try to curate categories and put them in trending lists so people don’t have to search for them07:36 – Where to experience i-moji09:47 – The team is 7 people full time and they’ve raised $2M of seed in equity10:27 – Advice on raising capital in the B2C space11:01 – Understand how it becomes a massive business12:35 – In the b2c space, you’ve got to have a following13:08 – Impression goal is in the billions per month13:75 – i-moji

Ben Fisher, the co-founder of Lean Startup Machine, and Alchemy. Listen in as Ben talks about his growth process with both Lean Startup Machine and Alchemy, what he learned, and what lessons can be applied universally. Ben, a New York City­based designer + hacker, co­founded Lean Startup Machine and Alchemy (acquired by Red Rover in 2013). Time Stamped Show Notes:01:08 – Nathan’s introduction 01:35 – Welcoming Ben to the show01:50 – Talking Lean Startup Machine02:00 – You will fail, you will focus on the wrong stuff.03:23 – Lean Startup Machine started as a weekend-long experiment04:25 – The ascension of Alchemy Labs06:14 – Collaboration software—Google Group meets LinkedIN07:30 – WeWork was one of the earliest customers…bottom line at $100/mo08:50 – By the time they raised $60K in funding, they realized they didn’t have the energy to build the company—they therefore jumped on an acquisition offer11:38 – Ben was drawn to Jordan because he’s a fantastic marketer12:27 – People pay a ton of money on user-acquisi

Jon Gillon, 7x startup founder, 4x failer, general Silicon Valley Hustler, and free-style rapper. Listen in as Jon shares his story of early failure, how he remained persistent, and how his latest startup Roost came to be. Time Stamped Show Notes:01:08 – Nathan’s introduction 01:30 – Welcoming Jon to the show01:53 – The 4 failures were Jon’s most important lessons02:40 – Did the friends and family round02:53 – Hiring an engineer is the hardest part of getting a business off the ground04:05 – Just in the failed businesses Jon’s raised $35K05:20 – Jon’s biggest competitors06:00 – 15% transaction fee on all Roost transactions06:29 – AirBNB for inanimate objects08:22 – How to look for a lead investor—it’s not a willy nilly process09:45 – Zipcar and Enterprise are big partners of Roost10:16 – Finding a technical co-founder at the start of Roost12:20 – http://www.medium.com/@jongillon Famous 5Favorite Book? – How to Win Friends and Influence PeopleWhat CEO do you follow?— Jack Dorsey What is your favorite online to

Matthew Bernman of Sonar, a business that makes is super convenient for customers to chat with the companies they buy from. Listen as Nathan asks Matthew about his journey into the startup game, Sonar’s financial backing, and their long-term development goals. Time Stamped Show Notes:01:09 – Nathan’s introduction 01:39 – Welcoming Matthew to the show01:52 – Why he left 500 Startups02:08 – Matthew always wanted to jump back into the startup game03:09 – Used to work with Teamly—a company that folded04:10 – Convertible note versus equity05:03 – Lead Cap negotiation05:34 – How Sonar makes money06:00 – 120 paying customers, on average contributing $2K per month07:30 – Customer acquisition is primarily through word of mouth08:05 – Month over month revenue increase is 35%09:20 – Inbound leads tend to convert at a much higher rate09:48 – 3rd party integration will also be a growth driver10:22 – Want to hit $1M ARR in 201611:49 – The interest is in taking a lasting vestment in the company Famous 5Favorite Book? – None

Olivier Pailhes, the CEO of Aircall.io, an app that lets you buy one or several phone numbers across the world, add teammates to your dashboard, and place & receive calls on existing devices. Listen as Nathan and Olivier discuss the importance of clearly outlining equity splits, and the importance of starting a business at young rather than old age. Time Stamped Show Notes:01:01 – Nathan’s introduction 01:23 – Welcoming Olivier to the show01:29 – Based in Paris01:42 – Worked for years in Strategy Consulting03:03 – What Aircall does04:57 – The conversation surrounding splitting equity06:19 – How much of the business Olivier still owns06:35 – Aircall charges per month and per seat07:08 – 2015 revenue08:08 – Finding new customers09:10 – The average customer pays $100 per month09:27 – Talking gross retention10:40 – Negative churn11:12 – Customer acquisition cost 13:01 – Sales Call Center is only 6 people15:00 – Aircall’s main goal is to secure a few HUGE customers15:40 – Want to grow revenue number by 5x per

Mohit Aron, CEO of Cohesity, a company that caters exclusively to the secondary data storage market. Listen as Nathan ask Mohit about his journey up and through Google (including his decision to leave), his trial and error experiment in entrepreneurship, and how he came to create Cohesity. Cohesity was founded in June 2013 by CEO Mohit Aron, who is regarded as the pioneer of hyper­convergence, the first architecture to converge compute and storage to simplify virtualization. Aron founded the infrastructure company Nutanix to bring hyper­convergence to market and served as its CTO before leaving to build Cohesity. Aron worked as a Staff Engineer at Google from 2003 to 2007, where he helped design the company’s innovative Google File System. He also served as Architect at AsterData, a leading big data analytics company that was later acquired by Teradata. Mohit holds a Ph.D. in Computer Science from Rice University. Time Stamped Show Notes:01:08 – Nathan’s introduction 02:00 – Nathan welcomes Mohit to the show

Nicholas Tart, one of the founders of AwesomeWeb, a freelance marketplace for people who do and need awesome work. Listen as Nathan and Nick talk about the journey to a viable product, the challenge freelancers face, and why AwesomeWeb is so different compared to Elance or Upwork. Nicholas Tart is the co­founder and product manager for AwesomeWeb, a professional freelance marketplace for people who do and need awesome work. He's focused on building a perfect SaaS web app that'll help other founders make their sites more awesome. Time Stamped Show Notes:01:01 – Nathan’s introduction 01:18 – Nathan welcomes Nick to the show 01:50 – Nick likes the show because Nathan asks good questions02:15 – AwesomeWeb is a great bootsrapped website02:45 – Spend $30K to get from idea to minimum viable product03:00 – Charge $17-$27 to participate on the business—the only people that pay are the freelancers04:08 – Walking through the growth of AwesomeWeb05:37 – More focused on creating a great experience than maxing out revenue0

Ep 197 Jay Baer, the world's most retweeted person among digital marketers. Jay is a renowned business strategist, keynote speaker and the New York Times best­selling author of five books. Listen as Nathan and Jay talk about the difference between a workshop and keynote speaker, the importance of having a “bad cop” on your team, and why being patient is grossly undervalued. Jay Baer is the world's most retweeted person among digital marketers. He is a renowned business strategist, keynote speaker and the New York Times best­selling author of five books who travels the world helping businesspeople get and keep more customers. Jay has advised more than 700 companies since 1994, including Caterpillar, Nike, Allstate, The United Nations and 32 of the FORTUNE 500. He is the founder of Convince & Convert, a strategy consulting firm that helps prominent companies gain and keep more customers through the smart intersection of technology, social media, and customer service. His Convince & Convert Media divisio

Brian Adams, CEO of Rumber Materials Inc, a company that manufactures composite material boards, sheets and molded products from 100% recycled tire rubber and plastics. Time Stamped Show Notes:00:57 – Nathan’s introduction to today’s show01:39 – Brian defines what Rumber does04:35 – How Brian came into Rumber04:49 – Know what you love to do and do it05:09 – Bought Rumber in 2012 for $5 million05:55 – Rumber turns about 30% of gross income into profit06:35 – The biggest challenge Rumber faces07:37 – Controlling the manufacturing process in the United States08:53 – This is a high-abrasion, industrial good09:19 – Pounds per hour is how the measure their performance—1,250 lbs per hour is a GREAT day10:43 – Find Brian on LinkedIn Famous 5Favorite Book? – Think and Grow RichWhat CEO do you follow?— NoneWhat is your favorite online tool?— Strategic CoachDo you get 8 hours of sleep?— YesIf you could let your 20 year old self know one thing, what would it be?—Don’t do it by yourself—partner with someone else, someone

Ep 195 Margaret Brown, the owner and publisher of Shelf Media a company that holds and manages a variety of free digital publications. Listen as Nathan and Margaret talk about the art of driving revenue from publishing, what it takes to turn a profit, and how digital publishing works. Famous 5 Favorite Book? – The Four Hour Work Week What CEO do you follow?— Alex Blumberg What is your favorite online tool?— BlinkPlan Do you get 8 hours of sleep?— No If you could let your 20 year old self know one thing, what would it be?—Embrace who you are and what you were meant to do. Time Stamped Show Notes: 01:10 – Nathan’s introduction to today’s show 01:45 – Margaret breaks down Shelf Media 02:40 – Invested less than 10K to get started 03:45 – Acquiring the 1st 1,000 readers 04:24 – The primary thing that got them on the map was media coverage 04:54 – Throw a lot of spaghetti at the wall and something will stick 05:38 – Press Rush 07:09 – Subscriptions to all Shelf content is FREE 07:39 – You have to believe in your

Ep 194 Engelo Rumora a property developer who also owns Ohio Cash Flow a multi-million dollar Turnkey Real Estate Investment company based in Toledo, Ohio that specializes in providing turnkey properties in the Toledo, Dayton, Cincinnati and Columbus, Ohio markets. Listen as Nathan and Engelo talk about establishing a secure property portfolio, the art of the hustle, and why you need to keep throwing the “mud.” Time Stamped Show Notes:02:00 – Nathan’s introduction to today’s show01:28 – Living as a “Recovering CEO”02:40 – Building a $1M portfolio at a young age03:45 – Engelo was losing money on his mortgage payments04:50 – Optimizing real estate investments for cash flow05:09 – Establish an end-goal? How much money do you need per month to live on your own terms?05:39 – Every piece of property you buy needs to bring you closer to your goal06:38 – Engelo was 23 when he started doing the real estate investment work07:05 – Making $80K per year as a laborer08:40 – Hope is not a strategy—it’s for people with termi

Ep 193 Jared Fuller (Recovering) CEO of PandaDoc, a company that’s focused on making the digitization of documents a simply smooth process. Listen as Nathan and Jared talk about venture debt, the hidden value of recurring revenue, and Jared’s famous title of “Recovering CEO”. Time Stamped Show Notes:01:05 – Nathan’s introduction to today’s show01:28 – Living as a “Recovering CEO”01:55 – Recurring revenue is the way to go02:09 – Screwed up lots of stuff, but that’s OK02:23 – MRR before everything crashed02:50 – Fought over stupid stuff that had nothing to do with getting customers03:20 – Make sure you start a company with someone who’s done it before04:12 – Get focused on getting shit done05:55 – Talking about PandaDoc—going after the document as a whole06:50 – How PandaDoc makes money06:55 – Panda could be profitable tomorrow if it wanted to be07:50 – Talking venture debt (Square1 and Silicon Valley Bank)08:12 – The revenue and books on PandaDoc are SO good venture debt made sense09:35 – 4% interest rate11:00

Ep 192 Nathan speaks with Cathryn and Allen, the founders of The Best Self Co., a business dedicated to helping entrepreneurs think big, stay focused, and get more done. Listen as Nathan and the duo talk about using Shopify to grow their business and promoting on Kickstarter.The BestSelf Co. started as a project between two entrepreneurs, Cathryn and Allen, who were on a journey to creating a life they loved, through building their respective businesses and being able to quit their day jobs. Time Stamped Show Notes:01:00 – Nathan’s introduction to today’s show01:28 – Cathryn and Allen join the show. 01:40 – Bestself.co is a company dedicated to people to help them become the best version of themselves. 03:40 – Cathryn and Allen got the idea for the company when they started applying the principles of successful time management in their work lives and started seeing results. 04:20 – They did a Kickstarter to fund their first big batch of products. 05:44 – BestSelf Co. makes about 70% profit margins per product

EP 191 Tony Stubblebine, the CEO and co-founder at Coach.me. Listen as Nathan and Tony talk about different branches of coaching and the latter’s claim to fame as Jack Dorsey’s last boss. Bio Tony Stubblebine co-founded Coach.Me (formerly knows as Lift) on the idea that positive reinforcement and community support could be deployed universally to help people achieve their goals. Prior to Coach.Me, he was the founder and CEO of CrowdVine Event Social Networks, which builds simple and powerful social software to help people connect and meet. He was part of the Wesabe launch team, Director of Engineering at Odeo.com and Engineering Lead for O’Reilly Media. He is the author of Regular Expression Pocket Reference (O’Reilly). Time Stamped Show Notes: 01:00 – Nathan’s introduction to today’s show 01:54 – Tony joins the show. * 02:27 – Tony refused to be interviewed for the book Hatching Twitter so that he could write his own book one day. His claim to fame is ‘the last boss of Jack Dorsey.’ 05:01 – Tony talks about

Ep 190 Matt Smith, the founder of Latergramme and Thinkific. Listen as Nathan and Matt talk about how the latter left a 10K MRR business to work on a marketing platform for Instagram. BioMatt previously started 2 profitable self-funded startups. Most recently he co-founded Latergramme, a visual content marketing platform that makes visual marketing a snap. The app one to aggregate, curate, schedule and optimize visual marketing campaigns across all visual social media networks. Time Stamped Show Notes:01:00 – Nathan’s introduction to today’s show01:29 – Matt joins the show.02:30 – Thinkific is a platform that allows one to create, market, and sell online courses.03:53 – Matt created Latergramme at a hackathon while he was also work on Thinkific.04:20 – Latergramme allows one to create a publishing schedule for Instagram that automates marketing. 05:17 – Matt was making about 10K MRR (monthly recurring revenue) when he left Thinkific for Latergramme. His brother is still CEO. 07:00 – Matt believes his company