An NBA Player’s Journey Into Alts

Diversification is a key to smart investing at every level.  In this bonus episode of The Yield, Milind Mehere and Spencer Dinwiddie take a deep dive into what it means to pursue financial freedom, the importance of financial literacy, and how money has played a role in Spencer’s life.  Washington Wizards point guard, Pac-12 all-conference honoree, Calaxy founder, sneaker designer, and entrepreneur, Spencer shares more on the importance of learning to manage large sums of money overnight as a budding NBA All-Star, and when he started to plan for life after basketball.

Key Takeaways:

[1:15] Widdie’s basketball, entrepreneur, creator, and philanthropic background. 

[3:32] A balanced approach to the calculated investing of an NBA salary. 

[5:56] Who first inspired Widdie to invest his time, talents, and money? 

[8:32] The importance of diversification in your investments. 

[10:45] The what, where, how, and why of investing in startups. 

[14:48] Why does Widdie continually expand his business and investment knowledge base?

[17:28] Widdie’s motivation and mentors when investing in entrepreneurial ventures. 

[19:33] The importance of philanthropy and giving back to your community. 

[21:05] Lessons learned from the Brooklyn Nets and the Detroit Pistons. 

[23:44] What’s next for Spencer Dinwiddle?

With successes as a basketball player, entrepreneur, creator, and philanthropist, the first question is: is there anything Spencer Dinwiddie can’t do? After sharing his one major weakness, Widdie shares the inspiration that led him to confidently- and humbly- pursue his love of entrepreneurship and his love of basketball. 

Widdie was drafted into the NBA at a very young age, and that amazing success brought with it a lot of money- and a fast and steep learning curve to handle it.  Widdie walks us through the approach that he has taken to managing an NBA salary, from traditional investments like real estate all the way to his higher risk- and potentially higher rewarding- investments in the cryptomarket.  And at every level his goals are clear- to realize his next level by making sound investments, not only in safer-bet investments but also in the aspirational market-plus returns that have the opportunity to be available in today’s hotter asset classes. 

Widdie’s depth and breadth of investments of his time, talents, and money all show just how essential diversification can be when it comes to a balanced approach to investing.  He shares the details of his three investment buckets- real estate in what he considers his “safer bucket”, investments in his NBA career as his perceived  “middle-risk bucket”, and blockchain and crypto in his described “asymmetrical bucket”- and shares just how important each bucket is to him.  As he says, if you only bet on one thing and that one thing fails, you’re done. 

As a passionate entrepreneur, Widdie has learned plenty about things to do and things to avoid when investing in start-ups.  First, he suggests making sure that you’re passionate about the products you’re investing in so that you can feel good about contributing to the company.  Second, he proposes looking for companies that align with your personal values and vision. And third, and most importantly to him, he advocates staying curious and humble about all that you still have to learn about any topic- whether it’s designing sneakers or investing in the crypto market, there are people who know more than you do and can teach you if you are open to learning from them. 

For more insights into the mentors that have helped Widdie along the way, the value of meaningful philanthropic investments in your community, and a look at what fans can expect from the new Washington Wizards team line-up, you won’t want to miss out on the end of this inspiring conversation with one NBA player whose approach to investing, education and entrepreneurship have made him infamous on and off the court.

Take all of our content on the go with you and listen on demand no matter where you are.  Subscribe on Apple PodcastsSpotifyYouTube, or wherever podcasts are available so you don’t miss an episode.

How helpful is this content?

Was this content helpful?

Sign up with Yieldstreet and be the first to know about our latest offerings, recent news, upcoming events, and more.

Your email will never be shared and will only be used for Yieldstreet updates. Already a Yieldstreet member? You're already set up to be notified.

Share this article:

Sign up for Yieldstreet in 3 easy steps

Sign up with your email address

Securely verify your identity and link a bank account

Verify your accreditation (if applicable) to access all of Yieldstreet’s offerings.

The Yield

Our weekly podcast providing ideas about how to make money work for you and bring you closer to your dreams.

Since inception, over $2.2B has been invested on Yieldstreet

Join today for free to access alternative investment opportunities.

1 Past performance is no guarantee of future results. Any historical returns, expected returns, or probability projections may not reflect actual future performance. All securities involve risk and may result in significant losses.

3 "Annual interest" or "Annualized Return" represents an annual target rate of interest or annualized target return and "term" represents the estimated term of the investment. Such target interest or target returns and estimated term are projections of the interest or returns and or term and may ultimately not be achieved. Actual interest or returns and term may be materially different from such projections. This targeted interest or returns and estimated term are based on the underlying investments held by the applicable.

4 Reflects the annualized distribution rate that is calculated by taking the most recent quarterly distribution approved by the Fund's Board of Directors and dividing it by prior quarter-end NAV and annualizing it. The Fund’s distribution may exceed its earnings. Therefore, a portion of the Fund’s distribution may be a return of the money you originally invested and represent a return of capital to you for tax purposes.

5 Represents the sum of the interest accrued in the statement period plus the interest paid in the statement period.

6 The internal rate of return ("IRR") represents an average net realized IRR with respect to all matured investments weighted by the investment size of each individual investment, made by private investment vehicles managed by YieldStreet Management, LLC from July 1, 2015 through and including Dec 22th, 2021, after deduction of management fees and all other expenses charged to investments.

7 Investors should carefully consider the investment objectives, risks, charges and expenses of the Yieldstreet Prism Fund before investing. The prospectus for the Yieldstreet Prism Fund contains this and other information about the Fund and can be obtained by emailing [email protected] or by referring to The prospectus should be read carefully before investing in the Fund. Investments in the Fund are not bank deposits (and thus not insured by the FDIC or by any other federal governmental agency) and are not guaranteed by Yieldstreet or any other party.

8 This tool is for informational purposes only. You should not construe any information provided here as investment advice or a recommendation, endorsement or solicitation to buy any securities offered on Yieldstreet. Yieldstreet is not a fiduciary by virtue of any person's use of or access to this tool. The information provided here is of a general nature and does not address the circumstances of any particular individual or entity. You alone assume the sole responsibility of evaluating the merits and risks associated with the use of this information before making any decisions based on such information.

300 Park Avenue 15th Floor, New York, NY 10022


No communication by YieldStreet Inc. or any of its affiliates (collectively, “Yieldstreet™”), through this website or any other medium, should be construed or is intended to be a recommendation to purchase, sell or hold any security or otherwise to be investment, tax, financial, accounting, legal, regulatory or compliance advice. Nothing on this website is intended as an offer to extend credit, an offer to purchase or sell securities or a solicitation of any securities transaction.

Any financial projections or returns shown on the website are estimated predictions of performance only, are hypothetical, are not based on actual investment results and are not guarantees of future results. Estimated projections do not represent or guarantee the actual results of any transaction, and no representation is made that any transaction will, or is likely to, achieve results or profits similar to those shown. In addition, other financial metrics and calculations shown on the website (including amounts of principal and interest repaid) have not been independently verified or audited and may differ from the actual financial metrics and calculations for any investment, which are contained in the investors’ portfolios. Any investment information contained herein has been secured from sources that Yieldstreet believes are reliable, but we make no representations or warranties as to the accuracy of such information and accept no liability therefor.

Private placement investments are NOT bank deposits (and thus NOT insured by the FDIC or by any other federal governmental agency), are NOT guaranteed by Yieldstreet or any other party, and MAY lose value. Neither the Securities and Exchange Commission nor any federal or state securities commission or regulatory authority has recommended or approved any investment or the accuracy or completeness of any of the information or materials provided by or through the website. Investors must be able to afford the loss of their entire investment.

Investments in private placements are speculative and involve a high degree of risk and those investors who cannot afford to lose their entire investment should not invest. Additionally, investors may receive illiquid and/or restricted securities that may be subject to holding period requirements and/or liquidity concerns. Investments in private placements are highly illiquid and those investors who cannot hold an investment for the long term (at least 5-7 years) should not invest.

Alternative investments should only be part of your overall investment portfolio. Further, the alternative investment portion of your portfolio should include a balanced portfolio of different alternative investments.

Articles or information from third-party media outside of this domain may discuss Yieldstreet or relate to information contained herein, but Yieldstreet does not approve and is not responsible for such content. Hyperlinks to third-party sites, or reproduction of third-party articles, do not constitute an approval or endorsement by Yieldstreet of the linked or reproduced content.

Investing in securities (the "Securities") listed on Yieldstreet™ pose risks, including but not limited to credit risk, interest rate risk, and the risk of losing some or all of the money you invest. Before investing you should: (1) conduct your own investigation and analysis; (2) carefully consider the investment and all related charges, expenses, uncertainties and risks, including all uncertainties and risks described in offering materials; and (3) consult with your own investment, tax, financial and legal advisors. Such Securities are only suitable for accredited investors who understand and willing and able to accept the high risks associated with private investments.

Investing in private placements requires long-term commitments, the ability to afford to lose the entire investment, and low liquidity needs. This website provides preliminary and general information about the Securities and is intended for initial reference purposes only. It does not summarize or compile all the applicable information. This website does not constitute an offer to sell or buy any securities. No offer or sale of any Securities will occur without the delivery of confidential offering materials and related documents. This information contained herein is qualified by and subject to more detailed information in the applicable offering materials. Yieldstreet™ is not registered as a broker-dealer. Yieldstreet™ does not make any representation or warranty to any prospective investor regarding the legality of an investment in any Yieldstreet Securities.

Banking services are provided by Evolve Bank & Trust, Member FDIC.

Investment advisory services are provided by YieldStreet Management, LLC, an investment advisor registered with the Securities and Exchange Commission.

Our site uses a third party service to match browser cookies to your mailing address. We then use another company to send special offers through the mail on our behalf. Our company never receives or stores any of this information and our third parties do not provide or sell this information to any other company or service.

Read full disclosure
Copyright © 2022 YieldStreet, Inc.