I literally just got off a call with an entrepreneur before writing this and the only thing I could think of afterwards "Oh my god that guy was selling me so much bull shit."
Oddly enough however, right before that call I was having a conversation with an entrepreneur who actually wasn't doing enough to hype up the real progress they were making. He was signing big deals with resellers, had grown his salesforce and on-boarding went quicker than expected, and his land and expand approach was gaining more traction than anticipated. And yet if I hadn't been prodding him for that info I never would have been aware of it.
And thats the problem, most entrepreneurs fall into one of these two extremes: tons of bull shit or zero self promotion.
It's such an important skillset however for any entrepreneur. Large corporations have so much inertia behind them to begin with that they don't need that same level of push. Who isn't going to take a call with the CXO of Coca Cola, IBM, or GE? They don't need to play up how things are moving forward because it's given that there is tons of action happening all the time.
Start-ups are exactly the opposite. You are constantly facing a headwind. You're always trying to prove yourself and establish credibility. People assume you are all talk and no walk. It's the founders' job to constantly beat the drum of success and make sure everyone in their network thinks "wholly crap these guys are really taking off!"
The goal you're shooting for is that simply being associated with you will become bragging rights. Everyone wants to be the person who was "in" with that company before they became huge. People love to add big popular brand names to their CV. Your objective is to become that brand and the only way up is through self promotion. Not bull shit self promotion but real self promotion.
I'm not talking about a bunch of flavored advertising. No one cares that you had a single conversation with a mid-level manager at a fortune 500. Telling me that you just added 100 new sign-ups is a vanity metric. Real self promotion is consists of a series of meaningful facts strung together so that when your audience considers them as a whole they think "wow this is getting big".
Remember that every piece of communication you put out there is a promotional opportunity. Yes your communication with the outside world will be more nuanced than "look at all of the cool stuff I'm doing" but entrepreneurs still need to take advantage of every opportunity to continue the drum beat: "success is inevitable, success is inevitable, success is inevitable..."
Okay so how does this work in a practical sense? Well let's start with a more obvious example: company updates. When you're sending out your regular company updates to investors, advisors, partners, board members, etc. (hint: if you aren't doing that you should be) self promotion is fairly simple. "This week we closed X new accounts, a Y% increase over last week. We're also in the final phases of negotiation with a new sales channel partner. When they previously partnered with ABC brand it led to Z more deals being closed by the end of the first year. The good news is we've already identified two other firms just like them we think we can establish a similar relationship with once this deal closes."
What if the purpose behind your communication is not purely to provide for an update but to ask for something? Say poking a prospective investor to see if they've had time to read over your pitch deck? "Hi Alison, I just wanted to check in to see if we could schedule a call to go over any questions you have after reviewing the pitch deck? By the way, I also have a quick update for you since we last spoke. We closed a distribution deal with XYZ company last week. When they previously partnered with ABC brand it led to Z more deals being closed by then end of the first year. Our plan is to get them on-boarded by the end of the month."
Get the idea? The clear implication in all of this is that you actually have good news to share. I'm sorry to report that if you don't, this method self promotion is not going to work out well for you. The best promotional efforts are simply highlighting real facts not a bunch a smoke and mirrors. The bulk of the work when it comes to self promotion is not in writing the copy, it's in doing the work that allows you to be able to tell a great story in the first place.