Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Blaine Anderson, CEO of Dating By Blaine, located in Austin, TX, USA.

What's your business, and who are your customers?

I teach men dating skills through coaching and online courses, so they can attract women they're excited about. My customers tend to fall into two buckets:

  1. "Engineers" who may or may not be actual engineers, but they are typically guys who are 20-40 years old, have great careers and personal lives, but feel awkward or unsure of themselves when it comes to women and dating.
  2. Divorcés. These are typically guys 40+ years old, who may have kids, who weren't expecting to be single again and could use a helping hand navigating dating given how much has changed with how couples link up over the past couple of years.

Tell us about yourself

I dove into coaching men full-time in 2020. Previously, I worked in the travel industry as a luxury travel planner (think high-end travel agent). The whole industry collapsed overnight when COVID hit in early 2020, and I was suddenly out of a job. I literally moved back in with my parents in Tucson! I'd helped my guy friends with dating since college and had long toyed with the idea of coaching professionally as a side hustle. With nothing to lose, I decided to dive into coaching full-time. I literally found my first customers on dating apps — I'd create profiles for myself that made it clear I was a dating coach and offered a free COVID-19 dating guide. This wasn't scalable — I'd get kicked off the apps quickly — but there was a ton of demand, which proved to me that there was a great business opportunity and opportunity to help people here.

My motivation is to help men feel less lonely and find partners! There's a loneliness epidemic amongst men in the United States, and nothing makes me feel more excited than celebrating a client win. I attended my first client wedding last weekend, and the "I helped make this happen" feeling I experienced was so fulfilling!

What's your biggest accomplishment as a business owner?

My biggest accomplishment business-wise has probably been reaching a seven-figure revenue run rate, which I hit in mid-2022. I could barely imagine supporting myself, let alone a team, with my business when I got started, but it's a true going concern now, and I'm crazy grateful.

What's one of the hardest things that comes with being a business owner?

The hardest part of my job for me is "turning it off" — I get emails from my clients and prospective customers 24/7, and it can be difficult for me to put down my phone. I'm learning to create more boundaries between my personal and professional lives, but it's not been easy, particularly because I'm so motivated to continue reaching and serving more men!

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Don't be afraid to go niche. I don't think I could start a successful business today as a "dating coach for men" — there's too much competition — but I know I could be just as successful going even more narrow (e.g., as a "dating coach for older men," or "dating coach for gamers," etc.). I think a lot of smart people, in particular, are afraid to go niche because they think it'll be too limiting, but the upsides almost always outweigh the downsides in practice.
  2. Find one channel to acquire customers that works, then lean into it. Most first-time entrepreneurs fail to understand (A) how hard it is to stand out and acquire customers and (B) how you only need to succeed at one channel to have a real business. Basically, rather than trying to put eggs in a ton of baskets, go all-out in one basket until you're sure it can't work before trying something else.
  3. Recognize that it may take longer than you want to start feeling like you're winning. I struggled for almost a year before it was clear that my coaching business could support me. You absolutely need to look for (and see) signs you're gaining traction with what you're doing — if you're not seeing any signs you're doing something wrong — but the financial success can take a while, so don't give up.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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