Entrepreneurs-journey.com Podcast By Yaro

Russ Heddleston is the co-founder and former CEO of DocSend, which was acquired by Dropbox for $165 Million in early 2021. Russ currently works at Dropbox continuing the vision he had for DocSend. During this interview we hear how Russ went from studying at Stanford, to working at a startup called Greystripe, then as an intern at Dropbox, and then launching his own startup Pursuit. Pursuit was later acquihired by Facebook, where Russ continued to work for two years. He shares some interesting insights into why Pursuit didn't take off and the lessons learned, which he then took into his next startup, DocSend. We spend a good amount of time talking about what marketing Russ and his team did to grow DocSend, how they revised their positioning and copy on their website to add fuel to their growth and how eventually the deal with Dropbox happened. If you like B2B SAAS startup stories, this interview is for you. Enjoy the podcast. Yaro Podcast: https://www.yaro.blog/pod/  Blog: https://www.yaro.blog/ --- Send in

Sara Mauskopf is the co-founder and CEO of Winnie.com, a marketplace platform that connects parents looking for childcare and preschool providers with over 250,000 centres around the USA. To date, Sara and her team have raised $15.5 Million in venture funding over three rounds, with the most recent $9 million series being led by Rethink Impact.  In this interview we first dive back into Sara's history as a math major, then moving over to computer science, which led her to a job at Google after graduation. She later left Google for Twitter, then left again to join Postmates, where she met her co-founder, Anne Halsall. Sara and Anne were a little unique as working parents inside Postmates, and realized how difficult it was to juggle raising children and maintaining full time jobs. One of the challenges was childcare, an industry that was still driven mostly by a word-of-mouth for finding good options. Sara breaks down all the steps from making the first version of their platform, how they built the supply

I'm resurfacing this interview from 2016 because recently (2021) the team at MacGyver HQ has been sharing this interview on their social media, so I thought it would be a great time to share it with those new to Vested Capital. It was quite a thrill to see the actual MacGyver twitter account tweet out this podcast, especially as I was a kid who grew up watching the show on TV in Australia. Here's how it all came to happen... ****** When I received an email offering a chance to interview Lee Zlotoff, the creator of MacGyver for the my podcast, my initial reaction was mixed. I was excited to speak to someone who created such an iconic show, yet I wasn’t sure if he would be a good fit for a podcast about online entrepreneurship. As I investigated what Lee was up to currently, it became clear that although he was not an online entrepreneur, what he is teaching is so relevant for anyone building a business or trying to solve their financial problems. The MacGyver Secret Just as ‘Mac’ the lead character on MacGyver

It's hard to summarize all the success of Wil Schroter. He's founded so many companies. Today he's founder of Startups.com, a business education site and suite of tools and resources for entrepreneurs, some of which were previous startups by Wil (Fundable, Bizplan) and some were acquired (Zirtual, Clarity). Wil got his start early online, initially exploring bulletin boards with a commodore computer. He then launched a web design agency, Blue Diesel, in 1994, again very early to a new industry. His agency grew, later merging with a more traditional design agency, creating a full suite offline/online marketing firm. In a surprise success, the firm landed a massive client worth $250 Million in billings, beating out many larger agencies.  Wil eventually exited his agency ownership shares when the company was acquired. As a youg guy of just 27 he had earned enough money to retire, yet he decided to get back into entrepreneurship. I enjoyed this part of the podcast because Will explained why it was a mistake

Tim Ferriss needs no introduction.  Author, lifestyle design pioneer, angel investor (Wealthfront, Uber, Facebook, Twitter, Alibaba, Shopify, Duolingo), peak performance bio hacker, accelerated learning leader and of course, podcast host. Tim first appeared on my original podcast all the way back in 2007 when few people knew his name and he was talking about his new book, the 4-Hour Workweek. In 2012 he returned to my podcast to talk about how to accelerate your speed of mastering a skill, the main topic of his new book at the time, the 4-Hour Chef. At the same time as we recorded that interview, I also asked Tim to record a secret interview just for my membership site members -- an interview where I asked Tim to explain what happened during the years BEFORE he wrote his first and most famous book. Today I'm excited to release this special trilogy podcast featuring all three interviews, edited and re-released as one big Tim Ferriss flashback. Tim is a superstar. So many entrepreneurs credit his book as a

Sonya Petcavich is the founder and CEO of Meowtel.com, an 'Uber for cat sitting' service where a vetted cat sitter will come to your house and look after your kitties for as long as you need them to. Full disclosure: I am an angel investor in Meowtel and Sonya via the Jason Calacanis syndicate.   When I first had the opportunity to invest in Meowtel I was immediately a yes because I love cats and would use a cat sitting service straight away since I travel as a digital nomad (assuming I had a cat again - I haven't since I left Australia in 2015). I also couldn't believe this service wasn't already widely available under one dominant brand because I've heard of similar services for dogs, for example Rover, which recently announced an IPO via a SPAC. Sonya is a great founder, who keeps us investors updated with regular reports on the progress of Meowtel.  Unfortunately, shortly after I invested Covid hit, which hurt Meowtel big time. Thanks to Sonya's decisive action downsizing her company, they

Paul Biggar got started as a computer engineer early in life. He became a specialist in the field of compilers (software engineers use compilers to test code to see if it works or not). He liked compilers so much he completed a PhD on the topic. Paul had a few false starts as an entrepreneur, including a stint in the Y-Combinator program, but nothing really took off.Eventually in his late twenties, while working at Mozilla, Paul foresaw that the process of compiling and testing software will move to the cloud. He had the skillset and experience to understand the need, so decided to launch another startup -- and CircleCi.com was born.Paul, along with his co-founder, built the first version of CircleCi, charging a monthly fee for access. They were able to acquire early clients thanks to a strategic investor who introduced them to 20+ companies who needed what CircleCI offered.The Road To A Billion Dollar ValuationDuring the interview Paul said he didn't expect CircleCI to one day crack unicorn status. At the ti

In episode 8 of Vested Capital I featured an interview with VC and entrepreneur Elizabeth Yin. During that interview Elizabeth shared the story of how she founded LaunchBit and later sold the business to Todd Garland, the founder of BuySellAds.com . This happened in 2013. In 2012, I had Todd Garland on my podcast, where he explained how he came up with the idea and launched BuySellAds.com as a startup he created during nights and weekends while he was working at Hubspot. I went back and listened to the interview and thought it offers some great insight into what Todd did to grow his company to an eight figure business.  Hence I decided to resurface it for you today as a Vested Capital flashback episode. Here's the original description I wrote for the podcast... Todd Garland is the founder of BuySellAds.com, an advertising management platform and ad selling service that I have to say I am quite jealous of. Why am I jealous? Because Todd has built a company – a company doing over $10 million a year in rev

In the second episode of the Vested Capital Mastermind, featuring Yaro and his three friends - Nick, Mani and Gideon - we answer a listener question about how to get started as an entrepreneur, Nick talks about his latest property investment, Yaro reveals he had an opportunity to invest ConvertKit and Mani and Gideon share updates from their companies. --- Send in a voice message: https://anchor.fm/yaro/message

Dan Young is the son of Chinese immigrant parents who fled China to escape communnism. He then went on to live the American dream, building several companies in the computer hardware space, becoming a multi-millionaire. Dan's first big success came in the early 1990s, when with his wife they launched a computer hardware business called PC Laptops.  By offering an unlimited service warranty, using stickers to help spread the word and a crazy television ad campaign, they grew from negative $27,000 in year one, to a million dollars in year two, then five million in year three and kept growing from there. Dan was quick to turn his business profits back into investments, buying stocks and property. This strategy continued throughout the almost thirty years since the company started, with Dan now having done over $600,000,000 in property deals. More recently Dan and his team launched an e-commerce retailer focused on high-end computers for video gaming, called Xidax Pcs, and Storage Whale, a cloud based low-co

Marcel Herz is co-founder and CEO of Tiliter, a company that is accelerating the democratization of computer vision.Presently they are focused on the grocery store industry, offering a device used at checkout to scan and identify fruits, vegetables, baked goods - anything that is loose without a barcode.This is just the tip of the iceberg however, as you can imagine being able to scan and identify real world objects will have countless applications, especially as the software gets better and quicker.I made a small angel investment in Tiliter via the AngelList platform led by Brendan Hill, a previous guest on my podcast. I'm excited by the traction Tiliter already has - currently in hundreds of stores around the world - and also where this technology is heading.You can listen in to this interview to learn how Marcel and his co-founders built the prototype of the Tiliter checkout, then began approaching large grocery store chains to test it out.Enjoy the interview. Yaro Podcast: https://www.yaro.blog/pod/Blog:

Bryan M Clayton is the co-founder of Green Pal, an 'Uber for lawncare' technology platform, connecting lawn mowing providers to customers all over the United States. Bryan got his start as a teenager when his father forced him to cut a neighbours lawn to earn some money. Bryan liked being in charge of his income and over the next decade went on to build one of the largest lawncare companies in his city, earning over $10 Million a year in revenue with a team of 150+. After a decade, Bryan decided to exit his company, selling the business.  It didn't take long for Bryan to realize he needed a project to focus on to stay happy and passionate, so he decided to jump back into entrepreneurship and even stay in the same industry. However, his new company was a pure technology play, connecting lawncare providers with customers using a website and app called Green Pal. Bryan explains during this interview the very hard first five years of his new business. He didn't want to risk the money he made selling his firs

Pili and Jason Yarusi are real estate investors who today focus on multi-family properties -- buildings that can house for example 90 apartments. They didn't start out focusing on this type of property. Like many, they began with renovation flips, buying single family homes, upgrading them, then selling for a profit. During this podcast Pili and Jason take us back through some of their pre-property investment days, including how they met working at a bar, but didn't get together for ten years. We learn about their first investments, how they switched to investing interstate using the support of a turn-key provider (a partner who helped source properties for them in other cities) and eventually, the mindset shift that led them to think really big, going after the multi-family market. As you can imagine, it costs a lot more to purchase a 90-unit building compared to a single family home. Jason explains some of the different types of financing they use today to purchase the larger buildings. If property investin

Nathan Barry is the founder and CEO of ConvertKit.com, an email newsletter platform for creators to send newsletters and run email marketing campaigns. Nathan is well known for transparency, sharing the behind the scenes growth in revenue of his company from day one. At the time of this interview, ConvertKit is generating over $28 Million a year in sales.During this podcast we first cover all the businesses and roles Nathan had before he started ConvertKit, from running a web design agency at 17, to building IOS apps, to running an information publishing business selling books and courses on digital interface design making as much as $250,000 a year.Then we switched into the origin and early stage growth stage of ConvertKit. This was a super insightful part of the interview as Nathan explained how after two years of stagnation at $2,000/month in revenue, over the next two years he ramped it up to $500,000/month in revenue.What a run that is!I also asked Nathan to explain his philosophy around raising capital,

Jonathan Little is a professional poker player with over $7 Million in career earnings from tournaments (both online and in person) and is one of the most popular poker coaches/personalities in the industry.He's also co-founder of PokerCoaching.com, a membership site and training community with over 5500 paying members, making it a multiple seven-figure business.I met Jonathan via Jason Calacanis and his angel investor syndicate. Jonathan is an active investor in all kinds of different asset classes, from NFTs to Magic: The Gathering cards, although he is of course most focused on poker.During this interview we go back in time to learn how Jonathan got his start in poker, how he quickly became a professional, earning as much as $30,000 a month playing a specific type of poker online. We also learn how he upped his game to the point where he won over a million dollars from one tournament - twice.There's a lot of wisdom in this interview, and while much of it seems specific to excelling at Poker, Jonathan's adv

Elizabeth Yin is the co-founder and General Partner of a venture capital firm that, and I quote from their website, invests in "hilariously early startups".Hustle Fund typically invests $25,000 as a starting point into startups that have yet to show any revenues. Instead, they look for traction in other ways, which Elizabeth explains in this interview.We also go back in time looking at Elizabeth's own history as an entrepreneur, starting a company called LaunchBit, an advertising network, which was eventually acquired by BuySellAds.com.Elizabeth and her company LaunchBit were graduates from the 500 Startups accelerator program. After selling her company, she returned to 500 Startups as an Entrepreneur in residence and later a partner. This was her entry point into the world of venture capital. Elizabeth explains what she liked about the 500 Startups methodology -- a global perspective, any person can be a founder -- and how that informed her own strategy when forming Hustle Fund. If you're considering raisin

Introducing a new experiment on the Vested Capital podcast - a group show with some of my best friends. Meet Nick, Mani and Gideon. Three guys I've known for years who I speak to on a regular basis.  Through our friendship we discuss all the topics that I cover here on Vested Capital, so I thought why not start a group show we can drop on the feed here once a month - or on whatever schedule we end up focusing on. I'm a big fan of listening in to conversations with people who are doing interesting things. Nick, Mani and Gideon are running startups, investing in real estate and crypto, thinking about things like lifestyle design, balancing family with work, being productive, and of course, generating cash flow and investing to grow capital. We don't yet have a name for this sub-show, so for now I'm calling it the Vested Capital Mastermind, since these guys have very much functioned like a mastermind group for me over the years. In this first episode I asked each of the guys to introduce themselves and expl

Jennifer Beck is currently the founder of Jihi.com, a CBD skin and body care producer that aims to help high performing people sleep better and recover faster.Before this, Jennifer was co-founder of Cannabase, a wholesale exchange platform for the legal cannabis industry, which was acquired for over seven figures by Helix TCS .I knew the cannabis industry was heavily regulated, but I didn't realize how much of a challenge it presents to potential founders until I heard Jennifer explain what she went through.While it's an exciting and growing industry, entrepreneurs who decide to get into the Cannabis space have to be ready to face roadblocks around financing, taking payments and even simple things like moving product from one place to another.Despite the difficulties, Jennifer was able to raise capital, build a team, and exit with equity in a newly publicly traded company. She worked at the acquiring company for two years, before she left so she could sell some of her shares. Using her capital, Jennifer then

I am resurfacing my interview with Greg Smith, founder of Thinkific.com, a Vancouver based SAAS servicing course creators, because this year (2021) Thinkific did an IPO on the TSX (Toronto Stock Exchange) raising $160 Million. As I type this, Thinkific has a market cap of $1.36 billion dollars, making it one of the rare Canadian tech unicorns. Greg and his brother launched the company initially with a much more hands-on approach (it was more like an agency service to begin with), and then slowly built out a software service. Today they offer a free and premium version of their platform, earning millions in recurring subscription revenue, employing over 70 full-time employees in Vancouver, all working to help people from around the world to deliver courses online. It All Started With Marbles… Greg and I traveled back in time to his first business venture as an 11-year old. He built a marble ‘theme park’ and invited the neighborhood kids to come over and play, and then sold them candy he bulk purchased. This w

Chris Bakke is currently founder of Laskie.com, a startup focused on becoming the Upwork for enterprise hiring. Previously he was co-founder of Interviewed, which was acquired by Indeed for 'mid 8 figures' after just two and a half years. Prior to this he worked as COO for 42Floors (acquired by Knotel) and RentJuice, which was acquired by Zillow, where Chris also worked for several years.Chris in this interview explains his part in all these companies, first starting as an early employee in the real estate tech space, which led to his first exit, gaining shares in Zillow (he explains what he did with the shares during the episode).After a couple of years at Zillow, Chris left to work for another real estate tech firm 42Floors, rising to become COO, and again enjoying an exit when Knotel bought the company.Chris was then 'pushed' to become a founder himself, after his co-founders won a hackathon and several angel investors where throwing startup capital at them to back their recruitment testing tech idea.This