At KingsCrowd, we work tirelessly to ensure you make wise startup investment choices and build a diversified portfolio that can potentially drive long term outsized portfolio returns. One element that we haven’t highlighted to date is how does one manage capital gains in a tax efficient manner?


This element alone can have significant impact on the level of returns that funnel back to your bank account during a liquidity event. One of the best ways to do so is to invest via an independent retirement account (IRA).


One company that is trying to make setting up and managing self-directed IRAs and 401(k)’s easier than ever is Rocket Dollar, founded by Henry Yoshida. We sat down with Henry to understand how Rocket Dollar can help to make your startup investing life tax efficient and thus drive the best returns back to you the investor! Check out how below.


And be sure to sign up for an account HERE.


Question: So how did you decide to found Rocket Dollar?


Answer: “I think Rocket Dollar is the embodiment of having to rethink the way we approach investing. Traditional investing is dead. The days of 60%/40% public equity to public bond investing have given way to an explosion of new investment platforms and choice.”


“My team and I are focused on connecting the trillions of dollars, held by millions of investors, to 21st Century investments with no taxes under the future of retirement.” – Henry


Question: For those that don’t know can you explain what Rocket Dollar is?


Answer: “Rocket Dollar makes it easy for individuals to unlock retirement savings. No longer trapped in the traditional mutual fund offerings of most custodians, these savings can then be utilized to fund a real estate project, buy a rental house, invest in a startup, or anything else allowed by the IRS.”

“Rocket Dollar eliminates all the hassle by making it affordable and accessible to unlock retirement savings. With a Rocket Dollar account, you have checkbook control to invest your money any way you want.” – Henry


Question: How does Rocket Dollar make it easier and more accessible to have your own Self-Directed IRA or Self-Directed Solo 401(k)?


Answer: “Rocket Dollar removes the complexity of investing your retirement savings on your terms. We guide our customers on every step of their journey towards a successful retirement including account setup, rollovers/funding, and compliance.”


“We have built a user-friendly dashboard that allows users to track all of their investments in one place and securely stores all of their retirement plan documentation for easy quick access.” – Henry


Question: What are the advantages of investing capital out of a Self-Directed retirement account?


Answer: “For individuals who are interested in investing in alternative assets such as direct real estate, private equity, business loans, or even cryptocurrency, the advantage of making these investments are the tax savings.”


“Millions of people are familiar with the tax deferred treatment of IRAs(Individual Retirement Account), but with Rocket Dollar you can invest in those alternative investments previously mentioned with the same tax treatment of any normal IRA account.”


“This can result in significantly higher returns on the same alternative investment you would have otherwise made regular money.” – Henry


Question: Specifically why would you recommend individuals invest in the startup asset class via their IRA?


Answer: “For those individuals who are both qualified to do so and comfortable with the risk, investing in the startup asset class with a Rocket Dollar type IRA can be very a savvy investment for an individual. If the investment does very well, you can save a lot of money through the natural tax deferred structure of an IRA.”


“I think far too many individuals have approached retirement plans such as IRAs with the wrong mentality.  Most people have fairly traditional mutual funds inside of their IRA and high(er) risk, high(er) return potential investments in non tax protected traditional accounts.”


“The built in advantages of an IRA, tax deferral and potential to control the distribution of proceeds from the account once you hit retirement age, would almost objectively indicate you should do the opposite: put your high(er) risk, high(er) return investments in an IRA type account with additional tax benefits and put your more traditional investments into regular taxable accounts.” – Henry


Question: If people want to learn more about your service offering where can they go?


Answer: To find out more about self-directed accounts and investing please visit or give us a call at 855-762-5383


Fun question for you. Being down in Austin. What barbecue place do our readers need to go when they are down in Austin?


Henry: Don’t let anyone know I told you, but the locals are more prone to hit the specialty taco restaurants in Austin. Barbecue, like most foods, has one serious limitation: it can only be eaten for one meal per day.  The beauty of Torchy’s Tacos, TacoDeli, and ATX Cocina is you can have the same food for all three meals.


Since startup investing is already a long game, investing for your future retirement with tax advantaged dollars into startups makes all too much sense.


We think this is a great place to manage your startup portfolio and stand behind the value of doing so. Be sure to sign up for an account if interested, and as always if you have additional questions please reach out at


Thank you Henry for your time and thoughtful responses. Be sure to sign up for an account HERE.