23 March 2022 |

Ep42: Reconcile: Get The Tax Tools Brokers Don’t Want You to Have



  1. How single flips become 6-figure tax bills: 02:03
  2. Your wallet isn’t private: 5:20
  3. A founder’s gameplan: 07:01
  4. The aha moment: 08:23
  5. The two reasons no-one’s helping you with tax: 10:56
  6. No such thing as a free NFT: 16:08
  7. Investing in LeBron: 20:30
  8. Using crypto to pay the bills: 24:00
  9. Watch this space 26:51

How Jaimin Desai is Democratizing Access to The ‘Smart People’ (And Saving You Money)

“I realized no investor really has a good idea how much they owe unless they have an accountant, but even an accountant doesn’t go in every day to crunch the numbers and see what’s going on.” Jaimin Desai, Founder and CEO of Reconcile Money.

Bored, frustrated and looking for a secondary source of income, day trading skyrocketed during the pandemic and platforms like Robinhood were among the first to cash in.

But for your average non-professional investor, successful (or not so successful trading) left behind a problem. A problem very few of the trading platforms want to talk about: Tax.

If nothing can be certain except death and taxes, to quote Ben Franklin, then to omit this key piece of the puzzle is to expose thousands of traders to payments they first of all weren’t expecting, but secondly might have mitigated given better advice.

And that’s where Reconcile Money steps in.

Tax Advice For Everyday Traders

Fintech has created smart solutions for people to trade, to predict outcomes and to keep track of wins and losses. But it hasn’t worked out tax implications. Why? Jaimin believes there are two reasons.

The first is that trading platforms simply don’t want to expose themselves to being sued on the back of giving out poor tax advice. The second is that tax efficiency services and wealth management are aimed almost exclusively at high net worth individuals, not your average day trader.

It was this combination that Jaimin faced as an investor and one as a founder he was determined to solve. Reconcile steps into that gap, democratizing access to tax professionals, helping people plan in advance and working through strategies to make sure they pay as little tax as possible within the legal parameters.

The platform works by connecting traders to tax professionals and will grow to include tax planning, as well as tax filing, tools. 

Crypto Tax Doesn’t Have To Be Taxing

Alongside the more standard stock trading is crypto, another area traders get hung up on. In the main because some believe crypto transactions aren’t taxable. They are and they’re easily trackable. Yes, even those NFTs that get airdropped into your wallet.

And Jaimin believes the IRS aren’t going to accept ignorance as an excuse for non-payment:

“Give the IRS a couple of years and they’ll be able to track it down pretty quickly. You have to have a better answer than, ‘ I didn’t know about this,’ when the IRS comes calling.”

From Wine to Real Estate

The traditional model of portfolios packed with stocks and shares is gone. Now owning shares in a bottle of wine, or a house is an everyday trading innovation.

But with innovation and the diversification of investments there comes a problem. And while Jaimin welcomes new business models and the ability to create liquidity pools from srcatch, a lack of documentation and reporting is a danger. Or at least it has the potential to be, if not handled properly.

The answer isn’t your traditional wealth management company but instead getting ahead of the curve, creating workable strategies and creating killer tax efficiencies. It’s where Reconcile is heading. An all-in-one-platform that takes the shock out of the financial year round-up, democratizing access to the ‘smart people,’ and making a dent in inequality.

Follow Jaimin:

LinkedIn: linkedin.com/in/desaijaimin

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