Why TING founder Simon Shepherd uses Sharesight

We talk with Simon Shepherd, financial advisor and founder of The Investment Newsletter Group (TING) about why he uses Sharesight, his favourite features and his advice to investors.

The Investment Newsletter Group

According to Simon, TING was born not out of the need for yet another investment newsletter, but for a standardised way of tracking the performance of the recommendations given by the various newsletters that are already out there.

“Each service had its own way of reporting results—some clearer than others—making it incredibly difficult to compare them apples-to-apples,” he says.

“Rather than wasting time sifting through different reports and methodologies, I wanted a single, reliable source that cuts through the noise and objectively tracks which newsletters are delivering real, consistent returns.”

Why Simon uses Sharesight

Simon is able to track newsletter recommendations through Sharesight, which he has been using since about a decade ago.

“Back then, there was no easy-to-use platform that accurately tracked both portfolio performance and tax reporting in one place,” he adds.

“As a DIY investor, I wanted a solution that was built for individuals like me—not just for professionals or accountants. Sharesight filled that gap.”

What Simon appreciates the most about Sharesight is the ability to get real-time, data-driven feedback on how his portfolio is performing.

“The numbers don’t lie—if my strategy isn’t beating the market, it’s instantly clear. It keeps me honest about what’s working and what isn’t,” he says.

“It helps me avoid classic behavioural traps like loss aversion and herd mentality. When you can see your real-time performance 24/7, it’s much easier to stay rational and make decisions based on data, not emotions."

Simon also appreciates having the ability to keep all his investment records in one place, fully backed up online, which eliminates the risk of missing data.

“It significantly reduces the risk of errors compared to manually tracking everything in Excel,” he adds.

“That’s how I used to do it, and I know many TING members did the same. Sharesight is just so much more reliable and efficient for tax reporting and record-keeping.”

Simon’s favourite Sharesight features include:

• Tax reporting: Particularly the capital gains tax (CGT) calculator
• Performance tracking: Both for his personal portfolio and for running TINGlive.com.au, where accurate reporting is key. This includes “since inception” performance reports, which he considers a crucial feature for assessing how an investment strategy has played out over time
• The ability to include or exclude closed positions: This helps fine-tune how he evaluates returns and decision-making
• Flexibility in viewing returns: The ability to toggle between monetary gains and percentage returns to get different perspectives on performance
• The share checker button: A handy tool for quickly checking the performance of any stock over time.

Simon’s advice for investors

According to Simon, one theme that is repeatedly brought up in his podcasts with investing experts is the importance of having a repeatable system—one that works across different market conditions.

He recommends an investment strategy that is:

• Tested through bull, bear and trendless markets
• Consistently benchmarked against a relevant index (ASX200, MSCI World, inflation, etc.)
• Disciplined and not swayed by short-term noise

“At the end of the day, sticking to a well-defined, data-backed process is what separates successful long-term investors from those who just react to headlines,” says Simon.

Become a better investor with Sharesight

Sign up for a free trial today to start tracking your performance and tax, plus gain access to a suite of powerful reports designed to help you make better investment decisions.

Disclaimer: This article is for informational purposes only and does not constitute a specific product recommendation, or taxation or financial advice and should not be relied upon as such. While we use reasonable endeavours to keep the information up-to-date, we make no representation that any information is accurate or up-to-date. If you choose to make use of the content in this article, you do so at your own risk. To the extent permitted by law, we do not assume any responsibility or liability arising from or connected with your use or reliance on the content on our site. Please check with your adviser or accountant to obtain the correct advice for your situation.

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