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Going Deep with Aaron Watson

Aaron Watson's show is a forum for having meaningful conversations about the passions, fears and problems of people from all walks of life. Guests talk about entrepreneurship, ultimate frisbee, finance and lifestyle design. Guests include Nathan Chan, Kevin Kelly, Bill Peduto, Morgan Housel, Noah Kagan, Tucker Max, and Barry Ritholtz.
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Sep 21, 2017

Scot MacTaggart is the creator and host of The Pitchwerks Podcast.  Having logged more than 20 years in sales, marketing, and entrepreneurship, Scot has built a diverse portfolio of experiences helping businesses of all sizes to get to the next level.  

 

If you're in sales, biz dev, marketing, product management or politics, The Pitchwerks Podcast is a fast, easy way to sharpen your tools each week.

 

Attend my one-day conference January 27th in Pittsburgh. Learn more here.

 

Scot’s Challenges; 1. Find the reason why you can unleash your creativity. 2. Determine the reason you’re doing what you’re doing.

 

Connect with Scot

Facebook

Twitter

Instagram

Website

 

If you liked this interview, check out previous episodes with Pittsburgh podcasters Marta Mazzoni and the Drinking Partners Ed Bailey & Day Bracey.



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Sep 18, 2017

Joe Calloway has no time for BS real estate gurus standing in front of Ferraris.

 

Instead, he’d prefer to offer his perspective. He’s built a $40,000,000 real estate portfolio through hard work, persistence, and patience. Being raised by a single parent in a two bedroom, low income apartment in Mt. Oliver doesn’t usually breed success, but Joe Calloway’s story is anything but usual. Joe went from those unfortunate circumstances to being the largest single family home buyer in Pittsburgh.

 

With little direction in life and few marketable skills, Joe enlisted in the US Navy in 1997. Using his military reenlistment bonus, Joe bought his first property in 2004. For his early projects he served as investor, contractor, designer, and property manager, giving him first-hand experience which proved to be invaluable.

 

Joe formed RE360 in 2009 and has grown the company’s rental portfolio to 270 units with a monthly gross rental income of $229,000. 2014 alone saw the rags-to-riches Calloway invest $5 million and purchase 72 homes, making him the largest housing buyer in Pittsburgh for the second year in a row. Not bad for the poor kid from Mt. Oliver.

 

Attend my one-day conference January 27th in Pittsburgh. Learn more here.

 

Joe’s Challenge; Don’t rely on traditional sources if you are unhappy with your current position. If you want something great, you have to make it yourself and get creative.

 

Connect with Joe

Facebook

Twitter

Website

 

If you liked this interview, check out my other interviews with people making moves in the city of Pittsburgh, like Bill Peduto and Grant Oliphant.



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Sep 12, 2017

When you are on a mobile device that does not use blockers against ads and trackers, YOU ARE PAYING $23 per month just to load the tracking and targeting scripts for ads. It’s a payday for both advertisers and your telecommunications provider.

 

This was part two. Don't miss part one!

 

Attend my one-day conference January 27th in Pittsburgh. Learn more here.

 

Brendan’s Two Challenges; 1. Adopt an good ad blocker like uBlock or Disconnect Me. 2. Read a real physical book in the sunlight.

 

Resources

NSA uses Google cookies to pinpoint targets for hacking (Washington Post)

Mobile Ads Cost you $23 per month (Medium)

Basic Attention Token Raises $35 Million in 30 Seconds (CoinDesk)

 

Sep 11, 2017

This interview has been split into two parts to make it more digestible.

 

Brendan Eich is an American technologist and creator of the JavaScript programming language. He is currently the CEO of Brave software, the next generation web browser. Brave loads major news sites 2 to 8 times faster than Chrome and Safari on mobile and is 2 times faster than Chrome on desktop.

 

If you liked this interview, check out the rest of my interviews with leaders in the blockchain and crypto space and my interview with Kevin Kelly about technological trends.

Sep 6, 2017

Mark Leslie was the founding Chairman and CEO of Veritas Software. During his tenure as CEO, the company went from 12 employees to 5,500 employees deployed globally, and from a revenue base of $95,000 per year to $1,500,000,000 per year. In 2000, Veritas was the 10th largest independent software company by revenue, third largest by market capitalization, and achieved the distinction of becoming a Fortune 1000 company.

 

From 1980 until 1990 he served as president and chief executive officer of two Silicon Valley high-tech start-up companies. His prior experience included sales management, sales executive, systems engineer, and OS programmer.

 

Mark Leslie is a successful retired entrepreneur and continues to be active in the Silicon Valley community.

 

Attend my one-day conference January 27th in Pittsburgh. Learn more here.

 

Connect with Mark

LinkedIn

Twitter

 

Resources

The Sales Learning Curve by Mark Leslie & Charles A. Holloway

 



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Aug 30, 2017

Darrin Grove, Truefit’s Founder and CEO, is a native Pittsburgher with a passion for innovation, technology, and values-based leadership.

 

Since its bootstrap beginnings in 1997, Truefit’s experience with new, disruptive technologies has positioned the company as a leader in helping entrepreneurs and organizations bring new software products to market quickly. Using their proprietary Idea Launch™ process, Darrin and the Truefit team guide clients through a proven path to create new and next generation software products. By involving a broad cross-section of company stakeholders, end users, and subject matter experts, Truefit helps product teams reduce risk and build confidence. Their principled approach and “start-up” mentality have proven to be an invaluable asset to companies looking for an entrepreneurial approach to software product development.

 

In addition to his work at Truefit, Darrin is dedicated to sharing his insight in innovation and entrepreneurship with the Pittsburgh community. He leads the Deal Flow Team for Software and Technology at BlueTree Allied Angels and advises start-up companies at the AlphaLab tech accelerator. He is also active on several non-profit boards to promote leadership, education, and urban renewal, and is a regular panelist and judge at events related to innovation.

 

Darrin’s Challenge; Think small. Focus on the small executions, pivots, and iterations that will move your work forward.

 

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Resources Mentioned

Lean Startup by Eric Reis

Prospect The Sandler Way by John Rosso

Good to Great by Jim Collins

Agile Manifesto

 

Connect with Darrin

LinkedIn

Twitter

Instagram

Website

 

If you liked this interview, check out my other interviews with Pittsburgh entrepreneurs.



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Aug 28, 2017

“If the rust belt has come to define the hollowed out industries of the Midwest, in the next ten years the paper belt will come to define the paper-based industries from Washington DC to Boston. In DC, they print money, visas, and laws on paper. In Delaware, companies incorporate on paper. In NYC, they print media on paper. And in Boston Harvard and MIT print diplomas on paper. I am dedicated to lighting the paper belt on fire.”

 

That’s straight from Michael’s profile.

 

Before co-founding 1517 Fund, Michael Gibson was vice president for grants at the Thiel Foundation and a principal at Thiel Capital. For nearly five years working for Peter Thiel, he has contributed research to Peter’s global macro hedge fund, assisted in teaching a course at Stanford Law School on sovereignty and technological change, and helped run the Thiel Fellowship.

 

He serves on the board of the Seasteading Institute. Before his academic apostasy, he was working towards a doctorate in philosophy at the University of Oxford.

 

Attend my one-day conference January 27th in Pittsburgh. Learn more here.

 

Michael’s Challenge; 2017 is the 500th anniversary of the 95 theses. Write you own declaration and post it somewhere in public.

 

Connect with Michael

Twitter

LinkedIn

Website

info@1517.com

 

If you liked this interview, check out our most popular interviews.


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Aug 23, 2017

Kenny Chen serves as the Program Director of Ascender, where he focuses his attention on curating and delivering innovation programs and building collaborative relationships with people and organizations throughout Pittsburgh, as well as nationally and internationally.

This culminates each year with the Thrival Innovation + Music Festival, which brings together local and international influencers for multiple days of innovation-focused programs followed by a two-day outdoor music experience. On the side, Kenny is the co-founder of involveMINT, and serves on the boards for the Pittsburgh Entrepreneurs Forum and Social Venture Partners.

Kenny was born in Madison, WI, raised in Las Vegas, NV, and graduated from UC Berkeley with a degree in Social Psychology. He has worked in several places around the world, including San Francisco, Washington DC, Taiwan, and Hong Kong. He came to Pittsburgh in 2014 for the Coro Fellowship in Public Affairs, a transformative experience that quickly gave him a wide breadth of knowledge and a deep love for the city.

 

Attend my one-day conference January 27th in Pittsburgh. Learn more here.

 

Kenny’s Challenge; Intentionally seek out opportunities to interact with and learn from someone who doesn’t share your beliefs, views, or background.

 

Connect with Kenny

LinkedIn

Twitter

Website

 

If you liked this interview, check out all my interviews with the people shaping the future of Pittsburgh.



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Aug 21, 2017

Erik Voorhees, CEO of leading digital asset exchange ShapeShift.io, is among the top-recognized serial Bitcoin advocates and entrepreneurs, understanding Bitcoin as one of the most important inventions ever created by humanity. Erik's former project, the groundbreaking gaming phenomenon SatoshiDICE, was, at its peak, responsible for more than half of all Bitcoin transactions on Earth and popularized the concept of "provable fairness."

 

You should attend my one-day conference January 27th in Pittsburgh. Learn more here.

 

Erik’s Challenge; Get some Bitcoin and learn how to use it. Block explorer

 

Like my crypto episodes? Support the work!

Ethereum: 0x1c5f5da1efad45078c41bceb18eb777099138e6b

Bitcoin: 13RcQZnZM4Lx6bw37YVdiv6Uc2X5b7anF3

 

If you liked this interview, check out all of my blockchain and crypto related interviews.



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Aug 14, 2017

Mark joined WebKite in the summer of 2016 out of his excitement for the advertising technology space and the powerful products WebKite has developed to date. Machine learning and language technologies can do so much still to connect consumers to the products they need, and WebKite will continue to be a major player in that work.

 

When not at work, Mark can be found serving as his neighborhood’s borough councilman, an advisor to small and family-owned businesses, a sous chef for his lovely wife’s kitchen creations, and the kooky uncle to his cute niece Lindsey.

 

Mark is a Carnegie Mellon University graduate who has been working as the CEO of early-stage software companies for about five years. His first company, Student InTuition, merged to form Imagine Careers, Inc., a first-of-its-kind career discovery and engagement platform in the human capital space.

 

WebKite, Inc. is an advertising technology company leveraging machine learning to create the most efficient and specific advertising campaigns on the web. With PPC, Remarketing, and Display products across a number of sectors, we make your inventory soar!

 

Mark’s Challenge; Find a business in your local community and find a skill or service that could be useful to them.

 

Resources

Google Adwords Certification

 

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Connect with Mark

Facebook

Twitter

LinkedIn

Website

 

If you liked this interview, check out all of our interviews with the most influential people of Pittsburgh.



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Aug 9, 2017

Barry Rabkin has over a decade of success founding, growing, and selling technology companies. An operational and strategic business leader, Barry's experience ranges from high growth, venture backed startups to Fortune 500 companies. He has also contributed to the development of over 100 successful physical and digital products.

 

Barry is proud to serve as Chief Marketing Officer of Identified Technologies, President of Hackers & Founders - PGH Chapter, Board Director of Jewish Family & Children's Services, He is also a guest Professor at Carnegie Mellon University and Strategist at Barry Brands Consulting where he advises and invests in many of the region's fastest growing start-ups.

 

Barry’s Challenge; Write out your do list for the day and systematically eliminate everything getting in the way of your primary goal.

 

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Connect with Barry

Twitter

LinkedIn

Website

 

If you liked this interview, check out episode 43 with Dick Zhang where we discuss Identified Technology for the first time, drone innovation, and entrepreneurship.


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Aug 7, 2017

Today’s episode is a conversation about Truth and Love. Both are often missing from our daily interactions, and Kim Scott wants to fix that.

 

Here NYT and WSJ bestselling book Radical Candor covers the leadership and communication lessons she learned while working for Sheryl Sandberg & Sergey Brin and Google and with Steve Jobs at Apple.

 

Whether you are a leader, consultant, or employee, you will benefit from injecting more radical candor into your meetings and discussion.

 

Kim’s Challenge; Focus on soliciting radical candor from someone you works with

 

Book

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott

 

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Connect with Kim

Twitter

Website

 

If you liked this interview, check out our other most popular episodes.

 

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Aug 2, 2017

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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Connect with Aaron

Twitter

Website

 

If you liked this interview, check out my interview with Wealthfront CEO Andy Rachleff and all of our other finance-related episodes.



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Jul 31, 2017

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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Connect with Ka

Facebook

YouTube

Website

 

If you liked this interview, check out my top interviews from over 230 interviews.


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Jul 26, 2017

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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Connect with Christian

Facebook

Instagram

Twitter

Website

 

2103 Penn Ave, Pittsburgh, PA 15222

 

If you liked this interview, check out our other interviews with Voodoo Brewery’s Jake Voelker and all the people shaping the future of Pittsburgh.


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Jul 24, 2017

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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Connect with Andy

Twitter

Website

 

Get an Additional $5,000 Managed for Free

Wealthfront.com/andy

 

If you liked this interview, check out all my other finance interviews.



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Jul 19, 2017

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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If you liked this interview, check out my most popular episodes.



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Jul 17, 2017

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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Connect with Bryce

Facebook

Twitter

Instagram

Website

bryce@10xtravel.com

 

If you liked this interview, check out all of my best finance-related interviews.


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Jul 12, 2017

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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Connect with Molly

Facebook

YouTube

Instagram

Venture Shorts

Boudoir Marketing Camp

 

If you liked this interview, check out our most popular episodes of all time.

 

 

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Jul 10, 2017

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

 

 

Like my crypto episodes? Support the work!

Ethereum: 0x1c5f5da1efad45078c41bceb18eb777099138e6b

Bitcoin: 13RcQZnZM4Lx6bw37YVdiv6Uc2X5b7anF3

 

 

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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Jul 5, 2017

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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Connect with Ed

Twitter

Website

 

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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Jul 3, 2017

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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Connect with Tom

Facebook

LinkedIn

Twitter

Website

 

 

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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Jun 28, 2017

Melissa returns to talk about her new Ultimate Frisbee Skills Course.

 

As a high level player and NCSA Certified Strength and Conditioning Specialist, Melissa is on a mission to improve the sport of ultimate by giving players the tools they need to train like the serious athletes they are.

 

In addition to writing The Ultimate Athlete Handbook and starting The Ultimate Athlete Project, Melissa gives ultimate fitness clinics nationally and internationally. Gain access to many more of Melissa's articles and videos by signing up for her email list at 25UltimateTips.com

 

Resources

1% Rule

Ren Caldwell

 

Melissa’s Challenge; If you want something to happen within the next 3-5 years, you need to start today.

 

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Connect with Melissa

Twitter

Facebook

LinkedIn

UltyResults

The Ultimate Athlete Project

25 Ultimate Tips

 

 

If you liked this interview, check out episode 18 for our first interview with Melissa, or check out our page of AUDL interviews. 

 

 

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Jun 26, 2017

Kevin Bupp is a well-seasoned real estate investor and host of the top iTunes show Real Estate Investing for Cash Flow. Kevin has over 16 years experience investing in single family, multi family, raw land, commercial and his favorite, mobile home parks. He comes on Going Deep to share his story and some secrets for success.

 

Kevin now uses his experience to educate other investors on how to locate, acquire and create "higher than average" returns in the misunderstood niche of Mobile Home Park Investing. The margins are incredible.

 

Kevin’s Challenge; Build a plan for buying a property within the next 90 days.

 

Book Mentioned

The Talent Code: Greatness Isn't Born. It's Grown. Here's How. by Daniel Coyle

Emerging Real Estate Markets: How to Find and Profit from Up-and-Coming Areas by David Lindahl

 

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Connect with Kevin

Facebook

LinkedIn

Twitter

Personal Website

Sunrise Capital

 

If you liked this interview, check out our other real estate investing episodes with Jason Hartman and Mark Walker.

 

 

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