Flyers on sidewalks, and bootstrapping out of needing to do that

Philip Morgan

Yes, website popups work.

So do annoying people on the sidewalk handing you nightclub flyers. That "works" too, and at least some of those who are interrupted on the sidewalk must bring the flyer with them to the nightclub, proving to the nightclub owner that handing out the flyers "works". If it didn't work, those sidewalk interrupter dudes wouldn't get paid, and I'm pretty sure they're not interrupting folks on the sidewalk just for fun.

Interruptions accomplish a goal, and do so in a measurable way.

I don't know enough about the nighttime economy to say what kinds of nightclubs interrupt folks on the sidewalk with flyers and which kinds don't, but if I had to guess, I'd guess that the super-successful nightclubs don't bother with the sidewalk flyers. This is because it sends a signal:

  • "We could use a few more warm bodies paying admission or buying drinks. We're not busy enough."

  • "We don't have much of a plan for getting more busy. Paris Hilton wasn't available, so we're interrupting you as you walk down the sidewalk instead."

  • "We're not meaningfully different, so this flyer will try to get you in the door with a free drink coupon. Anybody could offer that, but we're hoping our offer hits you at a time when you're feeling like you just need a freaking drink more than you need a specific kind of nightclub experience, and we're hoping one free drink leads to multiple paid drinks from our bar."

This signal--one of neediness and undifferentiation--is not one that a premium, desirable, successful establishment would want to send. Their reputation obviates the need to hand out flyers. They might use other forms of buying or earning awareness, but not the flyers-on-the-sidewalk method.

The bootstrapping problem

This seems to be simple: Just don't send that signal of neediness.

Just don't do it!

But then, we stop thinking about just the entelechy of your career as a self-made expert and we start thinking about your whole career over time and then we realize we have a bootstrapping problem. How do you get from actually needing to hand out flyers on the sidewalk--because your business is new or immature or you've only recently decided you want to move from ordinary to exceptional--to having a reputation that obviates the need for sidewalk flyers? That's the bootstrapping problem. How do you bootstrap your way out of commodity status and into the premium expert category?

A stake in the ground

Let me first take a stab at listing specific lead generation approaches that send a signal that's a lot like the dude handing out nightclub flyers on the sidewalk. To be clear, every single one of these approaches could *not* send this signal, but the way these approaches are typically used and the people who typically use them creates a horn effect (the opposite of a halo effect). In other words, the approach is neutral, but the type of business the approach is associated with is what makes it problematic.

Irredeemably flawed lead generation approaches:

  • Website pop-ups

  • Sales, discounts, or coupons

  • Completely un-targeted paid advertising

  • Completely un-targeted outbound marketing

  • Bait-and-switch webinars

  • Contests

  • Unsolicited tear-downs, delivered 1:1

Potentially problematic lead generation approaches:

  • On-site realtime messaging/chat ( makes one of these products)

  • Lengthy sales pages with heavy use of "persuasion" techniques

  • Targeted but unsolicited email or physical mail

  • Targeted but unsolicited phone calls or SMS marketing

  • Referral fees

  • Trade show booth

  • Search advertising

  • Targeted display advertising

  • Inexpensive digital products

  • Gated content (lead magnets, content upgrades, white papers you have to opt in for, etc.)

  • Website content personalization

  • Free consultation offer

  • Email course

  • Sponsoring a newsletter, event, etc.

  • Using a lead generation service

  • Retargeted ad

  • Being listed in a reputable directory (, etc.)

  • Test, quiz, survey used as on-site lead generation

  • Connecting and building trust through social media

  • Unsolicited tear-downs published online

Less problematic lead generation approaches:

  • Speaking as lead generation

  • Podcasting guesting

  • Hosting a podcast

  • Webinars

  • Independent original research

  • Intellectual property-based tools (benchmarking tools, calculators, etc.)

  • Publishing your thinking in a way that exceeds the threshold of "casual" either in terms in frequency, depth, or access. Beyond-casual frequency is 3x/week or more, beyond-casual depth is a book, and beyond-casual access is in a niche publication or a venue like HBR.

  • IRL or online events with high educational or relationship value

  • Certain types of press mentions/features, citations, or interviews

That's one hell of a list of lists, isnt' it! The un-nuanced version of the advice here is: avoid the irredeemably flawed approaches on the first list, try to focus on methods on the third list, and be very careful with the methods on the second list.

A bootstrapping proposal

The more nuanced version of the advice is this:

You are wanting to become a self-made expert, and you're wanting to become recognized as an authoritative expert. Along the way, you'll face the bootstrapping problem. How do you generate those first few leads for advisory services?

If you can, start with the third list above, the less problematic lead generation approaches. Here are the reasons you might not be able to start with that third list:

  • Lack of confidence

  • Lack of access (ex: lack of access to desirable or worthwhile speaking opportunities, no credibility as a podcast guest, etc.)

  • Lack of profitability (ex: you might not be able to fund your travel to desirable speaking opportunities at first)

  • Lack of know-how (ex: you might not know how to be an interesting podcast guest)

If any of these constraints prevent you from using at least one or two lead generation approaches from the third list, then use methods on the second list (the potentially problematic approaches), but with the following mindset. I'll phrase it as a corny mantra:

I will thoughtfully use lead generation approaches from the second list to move the needle for my business, but the needle I'm moving is not arbitrary numbers (email list subscribers, etc) but the things that stand in the way of me using lead generation approaches from the third list.

Said differently, the purpose of the lead generation approaches from the second list is secondarily to bring in needed reveue, but primarily to help you more quickly move into generating leads using less problematic methods--those listed on the third list.

This is how you address the bootstrapping problem.