DatingTriggers.com

Heather Ann Havenwood is a serial entrepreneur who entered online marketing in 1999, long before most people had internet access. By 2009, she launched DatingTriggers.com as an information marketing business to teach men how to date women from a woman's perspective. She identified a specific market gap: men wanted advice on dating and communication, and she had the copywriting and marketing expertise to deliver it.

The core product is deceptively simple: a 20-minute video sales letter selling a $47 one-time offer called "Dating Up." The funnel converts at 20-25% on the opt-in page, driving visitors to an email list. Since launch, she's sold between 1,200 and 1,500 units of the $47 product, generating roughly $56,400 in direct revenue from this single offer. However, Havenwood made a strategic decision early on: rather than obsess over funnel optimization, she focused on what she does best—email marketing and relationship-building.

Heather grew her 25,000-person email list through a combination of SEO, video SEO, podcasting, interviews, and affiliate partnerships. But the real goldmine wasn't her own product—it was promoting others' offers. She built relationships with high-quality affiliate partners like Digital Romance Inc. (Chris Ducker) and Gabriel Moore, promoting their dating products to her list. Her emails convert at 15-25% open rates and 10-12% click-through rates, generating about 300-350 clicks per send at roughly $1 earnings-per-click (EPC). This translates to $300-900 in affiliate revenue per email, and she sends 1-3 emails per day.

The affiliate strategy worked because Heather built genuine relationships first, giving value before asking for promotion. She committed to partners' launch schedules and provided consistent promotion, which made them reciprocate by promoting her offer. She learned that in the information marketing space, her expertise wasn't in creating fancy funnels—it was in email copy and audience relationships. So she doubled down on email marketing as her core competency, sending 1-3 emails daily as "entertainment value" for her audience. Unsubscribe rates remained low because she treated email as a media channel rather than spam. By 2015, affiliate marketing represented 80% of her ~$250,000 annual revenue, while her own product contributed only 10-20%.

Heather runs a lean operation with just three team members while generating six figures in annual revenue. She reinvests 70-80% of profits back into the business to fuel growth, avoiding the trap many entrepreneurs fall into of taking outsized salaries. She's intentionally stayed out of real estate despite her background as an investor, waiting for what she believes is an overheated Austin market to cool down. Her advice to her younger self—and to anyone listening—is blunt: get into online marketing early, forget college, and avoid student loans. For her, the information marketing space proved far more lucrative than traditional paths.