Invest Like a Boss

Latest Episodes:

22: Betterment CEO Jon Stein: A Decade of Pioneering Robo Advisory Sep 23, 2016

Show notes

Jon Stein is the very popular CEO of Betterment, a platform that is pioneering “Robo-Advisory” and a listener favorite. In fact, the term “Robo-Advisory” was one of the reasons we wanted to start the podcast. When we first heard about Betterment, it was clear a new modern era of technology and investment advice was now available. Aside from the platform itself, we wanted to hear about Jon’s story and why he started Betterment. And a very inspiring one it is. Betterment has been in the works for almost a decade. You’ll be intrigued to hear how and where it got started, and what the future holds.

Jon’s - LinkedIn

Betterment account sign up - For every friend who funds, you get 30 days free, and each friend gets 6 months free.

Meb Faber on Building The All Seasons Portfolio - ILAB 15

Money master of the game - Tony Robbins

Time Stamp:

03:00 - Starting Betterment in New York City

05:30 - John’s personal story behind Betterment

11:20 - Launching Techcrunch Disrupt

16:00 - Transitioning away from using financial advisors

18:00 - Staying the course during a decrease in market value

19L50 - Growth and infrastructure over the next few years

22:40 - Active vs. passive - Evidence based

25:00 - Opportunity for international investors

27:00 - Being an emotional or physiological advisor

31:10 - Benefits for active and engaged investors

34:00 - John’s advice to his younger self

34:53 - Sam’s investments in Betterment

38:38 - Two side effects to robo-advisor

44:50 - The downside to Vanguard

49:00 - Removing emotion to prevent a loss

55:00 - Why is Betterment right for you

21: Silver Bullion CEO: Why and How to Buy Precious Metals Sep 14, 2016

Show notes

Gregor Gregersen is the Founder and CEO of Silver Bullion in Singapore. It’s a state of the art facility that is truly innovating the category through transparency, technology and cost efficiency. If you do nothing else with this episode, checkout the video loop here of the Silver Bullion “Safe House”, you’ll be impressed. Gregor had an interesting experience during the 2008 financial crisis that led him to starting Silver Bullion that is a fascinating story in itself.

On this episode we compare different ways to buy and sell gold, what types of mints and coinages are most common, the comparison of holding physical gold at home or abroad, Singapore as a safe have, and evaluate a few of the systemic risks that face the global today. We also discuss the unique and intriguing P-2-P lending platform that Silver Bullion created where loans are secured by the borrowers precious metals. No matter what your experience in purchasing precious metals has been in the past, there will be something you can take away from this episode.

Relevant links for guest:

Silver Bullion

Recommended:

Currency Wars –James Rickards

Discussed (relevant links):

The Safe House (video)
US Gold Confiscation in the USA

Show notes:

02:00 – Why did Gregor get into precious metals business
05:12 – Gold nationalization in Western Nations
05:50 – A history on the gold standard
08:10 – Systemic risks in the global economy
10:30 – Comparing the different ways to buy and sell precious metals
12:50 – What precious metals does Silver Bullion sell
13:50 – Why the name Silver Bullion
14:30 – When did Gregor buy his first piece of bullion
15:55 – Living through the financial crisis as a trader
16:30 – Starting the storage component of Silver Bullion
19:30 – Creating consumer transparency in Silver Bullion
21:00 – Different mints and coinages
23:45 – Gregor’s favorite mint to purchase
26:34 – A 1000 oz bar!
27:35 – Why Singapore as a safe place to store metals
28:37 – Singaporean politics
35:00 – Trust, confidence, and security in Singapore
35:00 – Caning in Singapore!
39:05 – At what point does it make sense to use Silver Bullion
40:45 – Quarterly audits of the inventory
41:45 – Minimum buys at Silver Bullion
42:30 – A walk through the buying process at Silver Bullion
44:50 – Overview of storage capabilities
48:00 – Fees for storage
51:40 – The liquidity in selling gold held at Silver Bullion
53:15 – P-2-P lending through Silver Bullion (Asset backed)
57:05 – Collateralizing the debt in a conservative way
58:20 – Who can lend money on the P-2-P platform
1:01:25 – Who can open accounts with Silver Bullion?
1:04:30 – Shipping the gold overseas from storage
1:03:00 – Summary of owning precious metals and systemic risks
1:03:45 – Where does Gregor invest his money
1:10:40 – See Silver Bullion for yourself!

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20: Glints Co-Founders: Mastering Early Stage Start-Up Investing Sep 08, 2016

Show notes

If you have ever wondered how a start-up goes from a concept to raising venture capital, than you’ll love this episode. Glints, one of Singapore’s hottest start-ups is fortunate to be driving down a the dream start-up path: from finding an early investor, to joining an accelerator programme, to raising a seed round of investing, finally to closing a larger Series A financing round…all while growing their team from the 3 founders to now more than 20 people in Singapore and Indonesia. The Glints co-founders join us on the show and share their grand experience on determining valuations, finding investors, structuring the deals, and raising money.

Glints

Glints.com

Discussed (relevant links):

The Hub Coworking Space
JFDI Accelerator
Personality Test

Show notes:

01:20 – Founders story before starting Glints
01:45 – How Glints was started
05:16 – The early vision for Glints
06:30 – Joining an accelerator
08:30 – Taking their first angel investments
12:30 – Deciding on Ivy league school vs. Glints
13:30 – Dropping out of school in the USA to pursue Glints
15:15 – Demo day
16:25 – Coming up with a valuation for seed round
17:20 – What were you looking for in your early investors?
17:25 – Fundraising advice
18:30 – Finding a lead investor
24:00 – Inside the Glints office
26:00 – Expansion into Indonesia
29:00 – Financial growth + Series A
30:00 – Difference in Seed and Series A investment
32:00 – Increasing my investment in the Series A
35:45 – Entrepreneur to investor
37:40 – VCs vs. Angel Investors
40:00 – How to get involved in the start-up scene
41:50 – Using the Series A funds for expansion

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

19: Simon Black - Finding Outsized Returns Off the Beaten Path Sep 02, 2016

Show notes

Simon Black is the owner and figurehead of the popular publication Sovereign Man. We have been following Simon’s advice and putting it into practice for years, and had the opportunity to have a conversation with him geared toward investing.

Appropriately labelled “Finding Outsized Returns Off the Beaten Path” this episode focuses on how Simon utilizes his vast world experience (now visited over 120 countries) and enviable network to find investment opportunities around the world. From precious medals & Bitcoin, to agricultural projects and start-ups, Simon is about as well diversified as someone could get and his investment views are shaped through more experience that anyone could hope to obtain in a lifetime… or 2.

Relevant links for guest:

Website – Sovereign Man
YouTube – Sovereign Man HQ
Twitter – The Sovereign Man

Where are we:

Sam – Lviv, Ukraine
Simon – Santiago, Chile

Recommended (books, subscriptions):

Adventure Capitalist – Jim Rogers
Emergency – Neil Strauss

Discussed (relevant links):

August 2016 Income Report – Johnny FD
Peer Street vs. Lending Club – ILAB 13 with Brett Crosby

Time Stamp – Topic:

03:00 – Catch up about Chile
08:25 – Simons annual travel schedule
10:00 – Finding unique opportunities through boots on the ground
12:00 – Jim Rogers’ inspiring travel
14:30 – Simon’s background in Intelligence
15:00 – The importance of personal freedom
17:50 – Simon’s view on owning precious medals
23:05 – Liquidity in physical gold bullion
25:00 – What mint or coinage is the best to acquire?
26:30 – Purchases larger balls vs. smaller coins
28:45 – When do you own too much of something?
29:40 – How to purchase gold around the world
32:15 – Bitcoin vs. precious medals
33:00 – Where to hold Bitcoin
36:15 – Why you may not want to trust your bank
37:15 – Simon’s Sovereign Academy
40:00 – Where does Simon invest his money
41:00 – Why are private businesses great assets to own
44:00 – The power of network and connections
46:00 – The skill of investing
48:25 – Types of businesses Simon likes to invest in
50:30 – Control vs. dependence in business ownership
52:00 – Deal flow and private company management
53:30 – Invest in things you understand
54:45 – How can we invest along side of Simon
56:30 – Do things that make sense no matter what
58:15 – Finding out more about Simon and his investment approach

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

18: How to grow your IRA/401k to $100m tax free like Mitt Romney Aug 25, 2016

Show notes

Joshua Sharp of www.CompleteIRA.com is one of the most highly touted experts in retirement planning and investing. He turns the topic of retirement planning into a very exciting episode by illuminating some modern approaches to investing and growing wealth within tax free structures.

We dive into how Mitt Romney was able to generate $100m in tax free earnings in his IRA, and most importantly navigate some real world examples to give the listeners a shrewd example of how they may consider better structuring their own accounts. If you have ever wonder how IRAs, 401Ks, SEPs and a variety of other structures may be utilized to optimize your retirement savings than this is a great episode for you. We took a lot away from this episode and are making changes in our own retirement planning.

Relevant links for guest:

www.completeira.com

For a 15% discount at Complete IRA for Invest Like a Boss listeners go to www.completeira.com/ilab

Where are we:

Sam – Kiev, Ukraine
Joshua – Portland, Oregon

Additional Links:

Turn $50k into $3 Million with SEP-IRAs – ILAB 05

Time Stamp – Topic:

02:45 – Fundamentals of retirement planning
06:00 – Why retirement accounts are not for everyone
07:30 – 401Ks are a safer structure than IRAs
08:25 – IRA vs 401K fundamentals
14:00 – Investing in yourself for retirement
17:55 – Solo 401Ks for earned income savers
20:00 – Diversifying your retirement accounts
25:35 – Utilizing multiple retirement accounts
31:37 – Traditional vs. ROTH
34:20 – Why traditional accounts may be a gamble
39:25 – Converting traditional funds to a ROTH account
43:50 – Keeping structures simple
45:25 – Will the Government mess with our retirements?
52:40 – A self directed IRA gives you a lot of investing flexibility
1:01:15 – How Mitt Romney grew his IRA to $100m
1:06:30 – Ditch your SEP for a Solo 401K
1:14:00 – Is there a minimum age for retirement plans?
1:21:00 – advice for employees with earned income

If you would like to take advantage of a special offer with Josh for Boss members only please visit: https://completeira.com/ilab/

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

17: Top 12 Investment Tips: Learning from Episodes 1-16 Aug 17, 2016

Show notes

With 16 amazing episodes under the belt of Invest Like a Boss, Sam and Johnny sit down and discuss the top 12 takeaways and how they have applied this learning to their own investment strategies and overall portfolios.

Some major investment vehicles reviewed in previous episodes include investing in stocks, Peer to Peer Lending, asset allocation models, REIT's, Tony Robbins all seasons portfolio, annuities, and tax free IRA investing. Listen to the end of the episode to hear an update on our current portfolio's and possible future guests on our show.

Where are we:

Odessa, Ukraine

What we are drinking:

Sam – Corona with ¼ lime
Johnny – Beer “Lada brand Bar”

Recommended:

Timothy Ferriss – The 4 Hour Work Week
Robert T. Kiyosaki – Rich Dad Poor Dad
Mebane Faber – The Intelligent Asset Allocator

Discussed:
Reccomend Investment Platforms & Books – Resources Page
Travel Like a Boss – Ep 125 – Budget Traveling and Bulgaria & Ep 126 – Recorded in No Man’s Land
$25 Amazon gift card instructions – Bonus

Show notes:

(01:30) 1. Investing in stocks long term is not risky e. 16

(03:20) 2. P-2-P works much better when there is an underlying asset e. 13

(05:43) 3. Don’t obsess about asset allocation models, but be disciplined in sticking to it e.15

(08:56) 4. REIT investing is awesome, and low cost models like Fundrise may be the future e.12

(11:07) 5. Investing in yourself is the surest way to make exponential returns e.1, e.2, e.6, e. 7

(14:10) 6. Using leverage can get you rich, and also in a lot of trouble. e.4, e.7, e. 14

(16:50) 7. Tony Robbins All Seasons – good, but not perfect e.15

(19:27) 8. Annuities can help you sleep at night, AND the grow tax deferred e.4

(22:00) 9. Low cost funds/implementation are more important the optimizing asset allocation e.15, e.16

(25:08) 10. Do not re-balance your portfolio around what is currently working e.15

(27:58) 11. Invest Tax Free for retirement with a Roth IRA e.5

(31:54) 12. The internet holds many untapped investment gems for us to stay close to e. 10

(34:50) – Sam’s recent investment activity in REIT’s, Peer Street and Vanguard

(36:14) – Johnny’s recent small cap stock, Lending Club and Forex investment

(42:20) – Future guest to be on the show

(42:55) – iTunes review thank you shout outs

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

16: William Bernstein: Lump Sum Investing vs. Dollar Cost Average Aug 10, 2016

Show notes

William Bernstein is a financial theorist, neurologist and Best Selling author of several books, including one of our favorites, The Intelligent Asset Allocator. He shows independent investors how to build a diversified portfolio without the help of a financial advisor.

In this episode we talk the possible risk tolerance of an all stock portfolio and what age you should be when investing. We discuss major advantages and disadvantages of lump sum investing over a dollar cost average approach especially over a 12-month period. Lastly the importance of knowing financial history to choose the best time to buy stocks and how it correlates with GDP. Listen to the end to hear Williams advice he would like to give to his younger self and other inspiring investors.

Relevant links for guest:

Williams Website – http://www.efficientfrontier.com/

Where are we:

Sam – Bangkok
Bill – Portland, Oregon

Recommended Books:

William Bernstein – The Intelligent Asset Allocator
William Bernstein – The Four Pillars of Investing: Lessons for Building a Winning Portfolio
William Bernstein – A Splendid Exchange: How Trade Shaped the World
William Bernstein – The Investor’s Manifesto: Preparing for Prosperity, Armageddon, and Everything in Between

Discussed (relevant links):

Modern Portfolio Theory – http://www.efficientfrontier.com/ef/996/basics.htm
Efficient Market Hypothesis – http://www.efficientfrontier.com/ef/700/studio54.htm
The Bernstein Portfolio model – http://www.efficientfrontier.com/ef/996/cowards.htm
Do not dollar cost average for more than 12-months – http://www.efficientfrontier.com/ef/997/dca.htm

Time Stamp – Topic:

06:00 – How Bill got into finance
06:45 – A quantitative approach to finance
07:15 – The Intelligent Asset Allocator
08:15 – Modern portfolio theory
10:35 – The Bernstein asset allocation model
11:50 – Dialling up the stock exposure
12:15 – Stocks vs. bonds
13:00 – Risk tolerance
15:00 – Why stocks can be toxic in retirement
16:00 – Buying the basic asset allocation of funds
17:20 – The importance of sticking with an allocation
20:40 – Rebalancing your portfolio
22.15 – Simple vs. highly diversified portfolios
23:00 – Lump Sum investing vs. Dollar Cost Averaging
27:30 – The psychological part of investing
28:32 – Do not dollar cost average for more than 12 months
30:50 – What DCA buys you insurance against
32:00 – The importance of financial history
33:55 – GDP is not always correlated with stock returns
36:00 – What does Bill wish he knew 40 years ago
37:20 – Bill’s advice to young people

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

15: Meb Faber on Building The All Seasons Portfolio Aug 02, 2016

Show notes

Meb Faber is one of our hero’s in Finance. A high energy straight shooter that is highly explorative and analytical. He gave up his skis to catch the surf in Manhattan Beach while co-founding his company Cambria Investments Management. Many of our listeners already follow Meb through his blog, podcasts and many books, and had to chance to catch up with him about modelling an “All Seasons Portfolio”.

Originally introduced by BridgeWater’s Ray Dalio, the investment allocation was once again hyped up in its reintroduction of Tony Robbins new book Money Master the Game. Meb has researched and compared dozens of the most coveted asset allocation models dating back to the early 1900’s and we wanted to see how the All Seasons Portfolio stacked up against others like the Perfect Portfolio, and the 60/40. This episode is perfect for anyone looking to learn how to model a buy and hold portfolio and learn more about how today’s economic environment may give clues to future investment performance.

Links for Meb:

http://mebfaber.com/
Cambria Investments
Twitter

Where are we:

Sam – Singapore
Meb – Manhattan Beach

Recommended:

Money Master The Game – Tony Robbins
The Ivy Portfolio – Meb Faber
Global Value – Meb Faber
ShareholderYield – Meb Faber
The Intelligent Asset Allocator – William Bernstein
Triumph for the optimists – Elroy Dimson, Paul Marsh, Mike Staunton
Demographic Cliff – Harry Dent

Discussed:

The Idea Farm
The All Seasons Portfolio – Ray Dalio
David Swenson
Risky Party 160% model – Global Market Portfolio
The Capitalism Distribution (Longboard)
Vanguard
Betterment

Some awesome links to Meb’s content:

Tony Robbins All Season Portfolio
Risk Parity Model (*watch the first video)
Asset Allocation Strategies (*our favorite article)
Global Asset Allocation (*get Meb’s book free)
Meb’s Podcast

Timp Stamp – Topic:
09:20 – How Meb got into finance
10:15 – Starting up Cambria
11:00 – 1500 blogs in 5 years
14:00 – Traditional investment advice vs. modern
14:45 – Modelling a portfolio for the future
16:40 – Having an appreciation for history
17:45 – The world’s investment Gurus
19:10 – Comparing 6 great portfolio models
20:45 – Why low cost fees make a huge difference
21:45 – Why buy and hold allocations don’t matter as much
22:50 – Japan’s market was flat for 2 decades
26:22 – Foreign markets are reasonable or really cheap
28:27 – What does risk parity mean?
31:30 – The simple takeaway of risk parity
32:00 – Negative interest rates
32:30 – Will bond rates continue to rise?
33:45 – Why high yield stocks are now dangerous
42:00 – Where REITs stand at the moment
35:00 – How models performed in the inflationary 70’s
36:20 – Reviewing the ALL Seasons Portfolio
37:14 – “Go enjoy your Summer”
38:25 – Being asset class agnostic
39:00 – Home country bias
40:00 – Dollar weighted vs. time weighted returns
41:33 – Advisor value, talking you out of emotional moves
42:25 – Investment timelines
43:40 – Dliving through a bear market
44:45 – Designing a model for the future (Global Market)
45:50 – The Trinity Portfolio
48:40 – What is exciting about Emerging Markets
48:00 – Small Cap growth prospective
50:00 – The capitalism distribution
51:50 – Meb’s opinion on Robo Advisors
53:50 – Robo-Advisors in bear markets
54:45 – Why it’s a great time to be an investor
55:25 – Personal finance vs. investing
56:45 – How about TIPS?
58:55 – WWIII investment planning
60:00 – Final thoughts portfolios for the futures

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

14: Real Estate Investing Advice: 1-5 Properties Jul 28, 2016

Show notes

A deep dive into real estate investing with the host of the Australian Property Podcast, Jonathon Preston. At age 29, JP has already acquired 5 properties in Australia’s hot Real Estate market and is mastering the art of financial leveraging to continue to grow his portfolio. He started with a single 15% down payment on a single property and in only 4 years has been able to use that to scale and generate more and more cash flow.

We dissect his strategy in actionable steps for anyone to take and explore fundamentals of real estate investments including yields, applying for loans, property rights, cash flows, and market intelligence. JP’s story follows the steps outline in one of our favourite books Rich Dad, Poor Dad and is proof that with good execution you can start in real estate from just about nothing and grow your wealth fast.

Relevant links for guest:

JP on LinkedIn
The Australian Property Podcast

Where are we:

JP – Sydney
Sam – Singapore

Recommended:

Robert Kiyosaki – Rich Dad, Poor Dad
Steve McKnight – From 0 to Financial Freedom: How To Do It Today!
Steve McKnight – From 0 to 130 Properties in 3.5 Years
Steve McKnight – From 0 to Financial Freedom: How To Do It Today
Steve Mcknight – From 0 to 260+ Properties in 7 Years
Steve Mcknight – $1,000 in Property in One Year

Time Stamp – Topic:

02:45 – How JP got started in property investing
05:20 – Purchasing his first property
06:10 – Leveraging other equity to get a loan
08:00 – Australia property market strength
09:00 – How loan assessments work
12:00 – Qualifying people for loans
13:00 – How JP acquired properties 2, 3, and 4
16:30 – On-going management of the properties
20:00 – Refinancing to make raise more money
21:30 – How JP learned what he knows
23:45 – What happens in a AUS recession?
25:45 – Property acquisition goals
29:00 – What JP looks for in a new property
32:00 – Emerging markets in Asia
33:00 – Rich dad, poor dad
33:45 – Sam’s property investments in Thailand
40:05 – Guarantee 7% return investment properties
41:35 – Property rights AUS vs. Thailand
45:00 – Ownership of Thai properties
50:25 – Carrying costs of properties
53:45 – Our next moves in property investing
57:15 – REIT investing as an alternative
1:01:00 – JPs investment property investing advice
– Play in a market close to home
– Buy something you are familiar with
– Look for scarcity
– Look for an area where incomes have the potential to increase

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

13: PeerStreet vs. Lending Club Jul 19, 2016

Show notes

Interview with PeerStreet's co founder and COO, Brett Crosby which is the Peer-2-Peer lending platform that secures the loans against the borrower’s real estate. PeerStreet is unique in that to date they have never experienced a default, and have loan terms of under 12 months compared to other platforms that have minimums of 3 years. Brett and his Co-Founder Brew Johnson have the perfect background of experience between law, tech, and real-estate. In fact, Brett was the brains behind Google Urchin, which was acquired and became Google Analytics.

In this episode we discuss how the P-2-P lending space is changing, and how technology can enable more efficient deal flow and better lender-borrower matching. Enabled by sophisticated technology, PeerStreet uses Big Data to cross reference over 20 years of submarket data in order to vet and stress test each loan. We also do a deep dive into our 16 loan positions we currently have invested through the platform and what we can expect as an investor. The episode represents a great learning opportunity on the types of modern investing opportunities that we are passionately looking to discover and share.

*since we recorded the podcast, PeerStreet did have to finally file a notice of default on a loan, but still has zero losses to date.

Relevant links for guest:

Twitter
LinkedIn
About the PeerStreet team

Where are we:

Brett – Manhattan Beach, California
Sam – Singapore

Discussed (relevant links):

PeerSteet Explainer Video
PeerStreet website
AlphaFlow

Time Stamp – Topic:

02:45 – Initial investment into Lending Club
08:00 – Pausing automated investing in Lending Club
12:30 – Available investment PeerStreet dashboard
17:00 – Sam’s PeerStreet investment strategy
22:30 – What PeerStreet is
23:45 – About the turmoil in the lending P-2-P lending industry
24:30 – Why PeerStreet is a better asset class than Lending Club
27:20 – PeerStreet advantages over other platforms
28:40 – First lien definition
31:45 – What happens in the case of a default
34:30 – What attracted Sam to PeerStreet
35:15 – Brett’s background at Google
36:15 – Technology enabled advantage
36:30 – How PeerStreet was co-founded
37:15 – What is under the hood of PeerStreet?
39:15 – Vetting loans through technology
40:00 – Using Big Data to stress test loans
41:45 – Peer-2-Peer lending bubbles?
42:00 – Loan to Value ratios
43:00 – Valuing the properties through 3^rd parties
44:00 – What markets are hot on PeerStreet?
45:45 – Details on Sam’s account on PeerStreet
48:00 – The beauty of robo-investing
49:30 – How and when yields are paid out
51:10 – Loans through the platform
52:30 – Strategy to utilize on PeerStreet
54:00 – Brett’s recommendation for getting started
59:20 – Ways to find out more about PeerStreet
59:59 – Get in contact with PeerStreet support

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5 star review on iTunes and claim your bonus here!

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