When I started my sales career in 1998, my “tech stack” was a pager, a Thomas Guide, and a bag full of quarters for every working pay phone in South San Diego, my territory. I’ve seen the hype. I’ve seen the noise. And I’ve seen the true revolutions that have completely changed the game.
And yet, in my workshops and consulting with business owners, I continue to see the same five mistakes that keep modern professionals from becoming true Rainmakers.
Here they are:
1. No Strategy, Only Spaghetti
Too many teams operate reactively: “Let’s try this. Let’s see what sticks.” But Rainmaking requires strategy. Strategy is where imagination and innovation meet. It’s the blueprint that allows you to see the gaps in the market, and fill them.
When you pair imagination with AI, you suddenly have the ability to design bold, targeted strategies that put you directly in front of your prospects. Without it? You’re just throwing spaghetti at the wall.
2. Sitting on Dead Leads
Most professionals have lead lists, but few actually work them. They’re not in a CRM. They’re not segmented by goals, pain points, or desires. A Rainmaker doesn’t just collect names in their book of business. They cultivate relationships by working their book of business.
AI now makes segmentation easier than ever, helping you personalize your approach and breathe life into your book of business.
3. Ignoring the Data
When I started my career in the financial service industry, we didn’t even have a CRM and absolutely no metrics or data. Today we have the ability to see instantly if what we are sending out is working or not so much.
If you’re not tracking your CRM metrics, you’re flying blind. Open rates, click rates, engagement levels, these numbers tell you who’s interested and when to strike. If Joe Smith has opened your email 13 times, that’s your cue to pick up the phone. Rainmakers don’t guess, they use data as their compass.
4. Resisting Video
Video is the most underused (and resisted) sales tool in the modern workplace. And yet, it’s one of the most powerful. The other day, I received a video sales letter. I wasn’t even shopping for what was offered, yet I watched the whole thing and booked a call. That’s the power of video. With AI we now can make video scripting, editing, and even personalization accessible to every sales professional and entrepreneur. The ones who embrace it are already outpacing the ones who don’t.
5. Missing the Thought Leadership Opportunity
When I began my career in 1998, I couldn’t share my expertise with the click of a button. Today, we all can. LinkedIn is one of the most powerful rainmaking tools we’ve ever had. Yet too many professionals stay silent. Thought leadership is top-of-funnel gold. It builds authority, attracts the right prospects, and establishes trust. And with AI, you can streamline the content creation process without sacrificing authenticity.
The Thread That Runs Through It All: AI
The real problem isn’t just the mistakes, it’s ignoring the tools that can fix them.
AI is not a replacement for Rainmakers. It’s an amplifier. A partner in strategy, segmentation, content creation, video, and beyond.
And that’s why I created V School, a sales school for the modern professional.
If you’re ready to step into a new era of sales and break free from what’s blocking your Rainmaking abilities, let’s talk.