When the stock market is hitting record highs, it’s easy to feel torn. On one hand, you don’t want to miss out. On the other, you don’t want to buy in right before everything drops.
But Chris Sain, a financial coach, author and motivational speaker, says those fears often keep people from doing the one thing that matters most — getting started.
“The markets like momentum,” Sain told me in our Top 100 Money Experts interview for GoBankingRates.com. “New highs typically lead to more new highs. In 2024, for example, we had 57 new highs. So far in 2025, we’ve had 16. The market likes momentum.”
Don’t Try To Time The Market
Sain’s first rule for investors is simple: stop trying to outsmart the market.
“Never try to time the market,” he said. “If you have cash ready to deploy and the market is running high, dollar-cost average your way in. It’s likely looking to go higher.”
He encourages investors to take advantage of pullbacks instead of waiting for the perfect entry point that never comes. “Target the previous high as a viable entry during a market pullback,” he added.
Avoid FOMO And Stick To A Plan
When stocks are climbing, many investors rush to buy in — often with more money than they should. Sain says that’s where people get into trouble.
“In hot markets, one mistake investors make when they’ve missed a massive move is going in too heavy with their position size,” he said. “Consistent automatic deposits are the best approach and help you avoid FOMO.”
For Sain, the real secret is consistency. “Time in the market is better than trying to time the market,” he said. “Invest consistently. Automate your buys and trade with a plan. Risk management is key, and the goal is always capital preservation.”
When markets are surging, it’s easy to get swept up in the excitement — or the fear of missing out. But Sain said that kind of emotional investing often leads to costly mistakes.
He warns against impulsive decisions and emphasizes steady habits. “If you invest automatically, it removes emotion from the equation,” Sain said. “That’s what builds real wealth — not guessing when to buy or sell.”
Stay Balanced and Diversified
Sain believes that investing success comes down to balance — both emotionally and financially.
“A well-balanced approach helps keep your emotions in check,” he said. “Dollar-cost averaging promotes good investing habits. Diversification brings peace of mind, and sector investing — such as A.I. and other emerging technologies — helps capture growth and momentum.”
When those pieces work together, Sain says, investors can grow their portfolios without taking unnecessary risks. “When strategies like these are combined and implemented properly, investors can achieve above-average returns consistently in the market,” he said.
A Mission To Give Back
Beyond investing, Sain is focused on giving back. He recently launched a $1 million ‘100 Days of Giving’ Tour, traveling across the country to hand out $25,000 checks to families, individuals and small businesses in need of a fresh start.
The tour has already caught national attention with features in Black Enterprise and on his hometown NBC affiliate — but for Sain, the goal goes beyond headlines. “It’s about giving people a financial lifeline — and hope,” he said.