Going Deep with Aaron Watson

Risk is a word with numerous definitions. Riskalyze helps investors negotiate the risks they face.

Aaron Klein is the quintessential entrepreneur, spending his entire career working with entrepreneurial businesses at the intersection of finance and technology. He’s led companies or teams working on business operations software, payments technology for political candidates and causes, and mobile strategies for trading tools.

He co-founded Riskalyze in 2011 and has led the company through the building of its core technology. The company has grown to support over $2 billion in portfolios and twice been named one of The World’s Top 10 Most Innovative Companies in Finance by Fast Company Magazine.

Aaron’s Challenge; Find an apprenticeship to gain experience before starting your first business.

Resources

Nick Murray

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Ka Sundance is a location independent father of 6, YouTuber, and CEO of a $1 million heart-centered online business. Together with his wife Katie, he works to show aspiring business owners, coaches, and artists how to transform their lives and manifest more purpose, abundance, and freedom.

Today, Ka and Katie have impacted millions of people on social media, and have helped and inspired thousands of people to go from $0 to six figures in revenue by using principles they teach in their flagship program, Online Business School.

Ka’s Challenge; Don’t wait. Take action right now. Do something that makes you happy.

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Christian Simmons is a hustler and a visionary.

His company, Pennsylvania Libations, connects distillers, small businesses, and individuals, to one another with the intent of growing, experiencing, and preserving Pennsylvania spirits. He operates a one-of-a-kind retail store located in the heart of Pittsburgh.

In this discussion, we cover Christian’s long background in alcohol retail, how he has navigated regulatory hurdles, and his vision for the future. Learn more about the realities of living in an alcoholic beverage control state.

Christian’s Challenge; Wake up at 5am. Stop watching tv. Stop drinking so much. Get to work building something meaningful.

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2103 Penn Ave, Pittsburgh, PA 15222

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Andy Rachleff is Wealthfront's co-founder, President, and Chief Executive Officer. He serves as a member of the board of trustees and vice chairman of the endowment investment committee for the University of Pennsylvania and as a member of the faculty at Stanford Graduate School of Business, where he teaches courses on technology entrepreneurship.

Prior to Wealthfront, Andy co-founded and was a general partner at Benchmark Capital, where he was responsible for investing in a number of successful companies including Equinix, Juniper Networks, and Opsware. He also spent ten years as a general partner with Merrill, Pickard, Anderson & Eyre (MPAE). Andy earned his BS from the University of Pennsylvania and his MBA from Stanford Graduate School of Business.

Andy’s Challenge; Stop sitting on the sidelines and start investing in a diversified portfolio of index funds. Get an emergency fund.

Further Reading

Innovator’s Dilemna by Clayton Christensen

Innovator’s Solution by Clayton Christensen

A Random Walk down Wall Street by Burton G. Malkiel

Howard Marks, OakTree Capital Letters

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Get an Additional $5,000 Managed for Free

Wealthfront.com/andy

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This post is inspired by Scott Young’s The Essential Education: If You Had Ten Years to Learn Anything, What Would You Do? In his post, Scott outlines his Ideal Ten-Year Self-Education Quest.

The fundamental premise is decoupling education from economic preparedness. If you had 10 years to learn whatever you wanted, purely for the sake of learning what would you study?.

What broad-based education plan would excite and challenge you?

Think of this as the educational equivalent to the what-would-you-do-with-a-million-dollars speculation. Let’s go.

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In the fall of 2013, Bryce Conway started a website teaching people how to save money while traveling the world. He learned the ins and outs of the credit card industry and the bonuses that landed him reward points and frequent flyer miles.

During our interview, he shares useful tips like signing up for Starwood and Hyatt hotel’s cards and avoiding Hilton and Delta. We also discuss how he has built his business and served thousands of people through building his site.

Bryce’s Challenges

1. Google travel hacking.
2. Think about what you do and figure out 2-3 ways to make money off of that. Write your skill and how to turn it into a business and put them somewhere you can see it every day.

Resources

Book a Trip to Paris for Under $300?

$24k Thailand Trip for $166

Churning Subreddit

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[email protected]

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Molly Keyser has created two successful businesses, overcoming a common problem for entrepreneurs along the way. Beginning her entrepreneurial journey at 19 with just $0.81 to her name, Molly Marie first grew her boudoir photography business to six figures and became the envy of startup photographers everywhere.

Not long after you get over the hurdle of bringing in enough business to survive as an entrepreneur, she ran into a new roadblock—how do you scale your business in a way that allows you to work less, not more?

Requests started rolling in from other photographers wanting to know how she’d done it, presenting opportunities for additional revenue streams through digital products where she packaged her knowledge and saw her revenue explode.

Molly’s Challenge; Take a 14-day Email List building challenge. Set a goal and a plan out a method for accomplishing it.

Equipment

Canon Rebel Ti

Nikon D50

50mm 1.8 lens

Gift

Email List Building Guide

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Venture Shorts

Boudoir Marketing Camp

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Jack du Rose is a former jewelry and diamond artist, current blockchain nerd and co-founder of Colony.io & Ownage.io. He is phenomenally excited by the power shift our decentralised future brings. When not making $100m diamond skulls, or paradigm changing social platforms, Jack enjoys a nice cup of tea and a sit-down.

Dr. Aron Fischer received his Ph.D. in mathematics from the City University of New York in 2015. His specialization was in Algebraic Topology and Homotopy theory. Since his graduation, he has been studying homotopy type theory in his free time and is interested in how (higher) type theory can help us write safer smart contracts.

He is working for Colony in R&D, developing the governance protocols, and for the Ethereum Foundation's Swarm team where he is working on state and payment channels for the swarm incentive structure.

Jack’s Challenge; Get involved in the Ethereum community and subreddit

Aron’s Challenge; Conduct your own Ethereum transaction.

Resources Mentioned

Ethereum Subreddit

Ethereum Github

Gitter.im

KanBan - Toyota’s Revolutionary Product System

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If you liked this interview, check out Episode 221 with Ryan Snowden or 158 with Roger Ver for a discussion of blockchains and crypto.

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Ed Latimore is a man of diverse talents and interests. When he is not training for a fight or challenging your sensibilities on Twitter, he is thinking deeply about culture and philosophy.

Latimore is also a patriot, having served as a radio technician specialist in the Pennsylvania Army National Guard and an AmeriCorps volunteer. He is currently working to complete a degree in Physics and Electrical Engineering at Duquesne University.

When he is not strengthening his body for boxing, Latimore exercises his mind to stay sharp inside the ring by playing chess. He has traveled to Moscow and Berlin to compete against world-renowned chess players. Additionally, he is also a prolific writer having self-published several books and blogs regularly.

Ed’s Challenge; Do something you’re afraid of.

Ed’s Book

Not Caring What Other People Think Is A Superpower: Insights From a Heavyweight Boxer by Ed Latimore

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If you liked this interview, check out episode 66 with Zak Slayback where we discuss dropping out of college, the value of apprenticeships, and the future of work.

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Thomas Mulliez is the visionary entrepreneur behind iTREKKERS. Tom founded the company in 2014 after realizing that bringing together vetted professional captains and guides on one platform would help guarantee everyone a better experience in the outdoors.

iTREKKERS is a combination of Tom’s desires to share his love of nature and to simplify the process of booking guided outdoor activities. His mission is threefold: to get people to experience the outdoors through iTREKKERS; to help people get outdoors, period, by providing useful tips and referrals; and to educate people about the outdoors and ways to be mindful.

Tom’s Challenge; Take 6 friends or family members and spend 4 hours outdoors.

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If you liked this interview, check out Episode 97 with Adam Haritan where we discuss mushroom foraging, nutrition, and the great outdoors.

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