The Yaro Podcast

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 advice can be applied to other aspects of life, from being a startup founder, content marketing and when to invest versus when to spend your money to grow faster.

I enjoyed this one a lot, and I'm sure you will too.

Yaro

Podcast: https://www.yaro.blog/pod/

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 raising money for your startup this podcast is definitely worth listening to. Elizabeth breaks down what she looks for in an investment and some strategies for early stage companies based on her own experiences as a founder.

Enjoy the podcast.

Yaro

Podcast: https://www.yaro.blog/pod/
Blog: https://www.yaro.

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 explain what they are currently working on. We also discuss topics like real estate investing, productivity (also being productive with a family) and resource allocation.

Note this is very much an experiment, so we do appreciate your feedback on whether you like this format. We've never done a four-way podcast before, so even just learning the flow and structure is going to take some time.

If you have any suggestions for a different name for the show, or topics we should discuss on future episodes, or would like to send through a question for us to address (in audio or text format), email it through to [email protected].

Of course this group show will not in any way replace my regular Vested Capital interviews, so it's still business as usual there.

Enjoy the conversation.

Yaro

Podcast: https://www.yaro.blog/pod/
Blog: https://www.yaro.blog/

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 decided to fund a new company without outside investors, formulating her own CBD products and launching Jihi, a DTC and subscription CBD product range.

If you want to hear how a two-sided marketplace business was created and then acquired for over seven-figures, how Jennifer monetized her marketplace, and what it takes to launch a physical product in the CBD industry, this interview will definitely give you insights.

Enjoy the podcast.

Yaro

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.

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 was the first business project in a long line of entrepreneurial ventures Greg undertook as a young man, right up to the point where he graduated from university and became a lawyer.

While Greg was studying law, he created a blog to share lessons on how to pass the LSAT — the big test students need to pass in order to get into Law school.

He then created his first online course, also on the LSAT. It was very early days for selling courses back then, so Greg couldn’t find any good platforms to help, so he hired a programmer to whip up something basic within a month. That was 13 years ago, and his LSAT course is still selling online today!

Needless to say, the germ of the Thinkific business came from this first experience selling his own online course, but Greg would not begin his tech startup for many years yet. First, he had a career as a lawyer.

Although Greg loved working as a lawyer, he couldn’t fight the urge to build something of his own, and eventually left his job to start a business.

Greg explains how he made the decision to move back in with his parents to save money, and with his computer engineer brother as his partner, started the first version of what would become Thinkific.

I was particularly interested to learn how Thinkific grew into the company it is today, so we spent much of the second half of the interview diving deep into the journey of a software startup.

Greg talks about how they initially sold a much more hands-on service, how they decided who to hire first as they grew their team eventually to 70+ people (and still growing!), and why it eventually became clear they needed to build a platform to service their ideal customer.

If you’re interested in starting your own SAAS or subscription-based tech startup, I think you will find a lot of what Greg did with Thinkific during the early days very insightful.

Enjoy the interview,

Yaro

Podcast: https://www.yaro.blog/pod/
Blog:

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 led to an amazing two and a half years where thanks to a lot of a hustle and a 'beachhead' client acquisition strategy, Chris and his co-founders grew Interviewed to $2.5Mil in annual run rate, and then the incredible sale to Indeed for almost $50 Million.

The world of music rights is a lot more confusing than I thought. 

There are many stakeholders who are all supposed to get a share of the revenue from music used online - from labels, publishers, platforms, song writers and of course the artist who created the music.

Jeff Ponchick worked in the world of digital music and knew well all the paper work required to make music rights work. 

He decided to start a company that attempted to digitize the music rights process, and thus make it a lot easier for artists to make money from their work.

Like many startup founders, Jeff first tested his idea with a not-so-scalable, very manual process -- working out all the details by hand, sending emails, making phone calls and filling out forms.

He did this for some test artists, who loved the service because it made it so much easier to get paid for their music no matter where it was being used online.

Jeff then brought on a technical partner, and they went to work to create the more scalable version of their service, to digitize the music rights process.

Thus Repost Network was born.

Jeff's idea proved to be a good one. Artists loved the service and of course loved getting paid for their work.

Musicians began to spread the word and Repost Network became a popular choice to help deal with music rights and negotiate with all the different music distributers - from YouTube, to Spotify and SoundCloud.

The word 'repost' in the name of Jeff's company refers to the goal of SoundCloud users - to get your tracks reposted so you can reach more people. Jeff maintained a close relationship with the SoundCloud team, which eventually led to an acquisition offer.

Repost Network was acquired for $15 Million in a cash and equity deal by SoundCloud in May of 2019. Jeff joined the SoundCloud team, where he still works at the time of recording this interview.

Jeff was very open during this podcast, sharing all the amazing steps that led to Repost Network growing to the point that SoundCloud was interested in an acquisition, and how the deal got done. 

Enjoy the episode.

Yaro

Podcast: https://www.yaro.blog/pod/
Blog: https://www.yaro.blog/

In the previous episode of Vested Capital (EP2), we talked with David Horne and Marty Balkema, founders of Calm Capital. They had recently acquired the company Wavve.

On this episode, Baird Hall, one of the co-founders of Wavve, shares the other side of that acquisition, as the seller of Wavve.

Baird takes us back in time to the origin story of Wavve, how it was a spinoff company from their first business when they needed to create audio snippets for sharing on social media.

The spinoff companies continued when they needed to create captions for audio within Wavve, which led to the creation of ZubTitle, a company Baird co-founded with a different partner.

Both Wavve and ZubTitle grew to earn over $100,000 a month each - 7-figure companies.

ChurnKey, Baird's latest company that helps subscription businesses deal with churn, was created as a result of needing to solve the churn problems within Wavve and Zubtitle.

Baird, as you can probably tell, is amazing at using a need in one company as the genesis to create a new company.

Of course, it's very challenging to grow one company, so working on two or even three at the same time rarely works. This is one of the reasons Baird and his partners made the choice to sell Wavve, so they could move on to focus on ChurnKey.

All of these companies are covered in this interview, which I know you will enjoy if you like SAAS startup stories leading all the way to exciting exits.

Enjoy the show.

Yaro

Podcast:

David Horne and Marty Balkema are founders of Calm Capital, a holding company with at the time of this recording, 10 companies under management with $8 Million in total annual revenue. 

The holding company model, popularized by Warren Buffet and Charlie Monger with Berkshire Hathaway, is becoming more and more common in the world of online business.

David and Marty help demystify what exactly a holding company investment strategy is and take us through an example acquisition, their first company purchase of Pttrns, in this podcast interview.

We also learn how the guys met, how they transitioned from being founders to investors and acquirers of other companies, and what financial structures they have used to finance their acquisitions.

I'm fascinated by this emerging trend of online holding companies for many reasons. It gives tech entrepreneurs an additional pathway for exiting their business, and it's an exciting way to compound your capital, increase cash flow and diversify your income as an owner of many companies. 

As an entrepreneur who enjoys having multiple projects, what Marty and David are doing really appeals to me. You get to enjoy owning companies in many different niches, but you're not stuck in the day-to-day trenches of running the companies.

Enjoy the interview, and please share it with anyone you think could benefit from hearing from these two trailblazing entrepreneurs.

Yaro

Podcast: https://www.yaro.blog/pod/
Blog: https://www.yaro.blog/

Mark Asquith, otherwise known as the 'British Podcast Guy' is the founder of several podcast related companies, including Captivate.fm, a web hosting, analytics and distribution SAAS for podcasters.

Mark, like many entrepreneurs, got his start with an agency doing general web and media development services. Eventually this led to a spinoff podcast specific web design company, which Mark and his Co-Founder left the agency to focus on.

After entering the world of podcasting Mark never looked back, launching his own shows, attending conferences and building more support services for podcasters. He also has plans for a team engagement tool, which he recently patented and will be launching soon.

I wanted to speak to Mark because there is a difference between running an agency and building websites, to then diving into the world of SAAS and now also physical products. 

It's not easy to make all these different types of business models work, but as you will hear in the interview, Mark had a method and a plan for moving from one focus to the next, allowing a business to grow, adding a team, then moving on to the next step.

Enjoy the interview.

Yaro

Podcast: https://www.yaro.blog/pod/
Blog: https://www.yaro.blog/