Extra Extra
Extra Extra is a newsletter about the tactics and mindsets that drive early startup sales. I’ve helped dozens of startups get results like a 50x in repeatable revenue and a 400% lift in sales calls per week.
My top founder regret
EXTRA EXTRA A newsletter about early sales from The Extra Group Read in browser I find it helpful to reflect on things I wish I’d done differently when I was selling at my startup, Skillist. And there are oh so many to choose from. 🥴 One mistake that haunts me I think a lot about is that I put far too much stock into any given deal. I would cherry-pick only the positive indicators: the prospect was friendly, they paid our platform compliments, they were open to chatting again. I would be...
The Pratfall effect
A friend of mine is a talented videographer. They've shot music videos, commercials, and ads. They recently got a new job as a videographer for a hot beauty brand. It's carried in Sephora, and has over one million followers on Instagram. A few months after my friend started the new job, I headed over to the brand’s Instagram to admire their work. It was awesome. And it was also completely different than what I expected. The video quality is pretty lo-fi. They look like they're shot on an...
When confidence backfires
Who doesn’t want to be a bit more confident? Confidence is, of course, a powerful and positive thing. It helps you silence your inner critics, beat back imposter syndrome, and be more resilient when things don’t work out. But as I’ve worked with more and more founders, something’s been nagging at me. We’re missing nuance around confidence. Not all confidence is made equal. Sorry, Demi. I want every founder to feel confident in their ability to figure it out. I want you to feel confident that...
The thing about your pipeline problems
I spend a lot of time unpacking the mental barriers that keep founders from hitting their revenue goals. Most sales blockers affect founders who struggle to sell. They might get nervous on sales calls, or are waiting for their product to be perfect. But I’ve noticed one obstacle that affects founders who are already selling hard. These founders tell themselves: "I just have a pipeline problem." They attribute slow growth to tactical problems with their sales funnel: "I just need more leads."...
The mental game of sales
Olympic athletes do not play about their mental game. So why do founders? Name an Olympic athlete. Guaranteed, they've got a kinda-out-there mental ritual that helps them perform and win. Michael Phelps famously ran through visualizations before every race. He didn't just visualize what every second of a winning race would feel and look like -- he went through the worst case scenario too. This practice kept his anxiety at bay (and also helped him win gold in Beijing when his goggles had...
The planning fallacy
Nearly everything takes longer than we expect. It’s the recipe with a cook time of 25 minutes that somehow took you 90. It’s the construction site down your street that was supposed to be finished last year. And it’s definitely every project that you take on at your startup. It’s not you. It’s a real thing. It’s called the planning fallacy. Iconic economists Daniel Kahneman and Amos Tversky discovered this cognitive bias, which holds that humans are really, really good at underestimating how...
Outreach methods that match your stage
Founders often assume that sales processes of a later-stage company are what they should be doing too, like building out an automated sales sequence. It feels grown up. It feels like the obvious thing to do. But the average outbound sales sequence for a later-stage org is built on things that early startups just don’t have. Things like: A proven target market that has been sold to consistently and successfully over a period of time Clarity of that buyer’s honest needs A definition of their...
Don't set that goal
I work with founders who are new to sales, and those who’ve been at it for years. They all ask the same question: “what should my sales goal be?” And I do have some answers. I’ve got recommendations on how many sales calls you should have a week, how many hours you should spend on selling, and what a good email deliverability rate is, so you know your emails aren’t going straight to spam. But I’m also very hesitant about setting goals, for two big reasons, depending on your stage. For...
The customer is not always right
Read in browser So, let me be clear. The customer is right often. If a buyer doesn’t perceive something as high on their list, they’re right about that. No persuasion will change their mind. If the customer isn’t satisfied with your support once they start working with you, they’re right about that, too. Their perception is their reality. But when it comes to the sales cycle, prospects can be misguided. Here's a common one: buyers often speed ahead and want to see the product within the first...
Altitude sickness, startup style
A founder client of mine* once said that she deals with “startup altitude sickness.” I’d bet you’re right there with her. Multiple times a day, a founder goes from down in the weeds to 10,000 feet. One moment, you’re fixing product bugs, analyzing open rates, or checking for spelling errors in a new sales sequence. And then, you elevate. Often, it's not even a conscious choice. You’re writing an email, and all of a sudden you’re looking down at your startup, asking existential questions like…...
Extra Extra is a newsletter about the tactics and mindsets that drive early startup sales. I’ve helped dozens of startups get results like a 50x in repeatable revenue and a 400% lift in sales calls per week.