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Photo by Valentino Funghi on Unsplash

When faced with setting your strategy or making an important decision, how do you know you’ve considered enough diverse options and can proceed with confidence?

If you’re like most folks, you might rely on intuition coupled with readily available information—you just go with your gut. This is called taking the inside view:

An inside view considers a problem by focusing on the specific task and by using information that is close at hand, and makes predictions based on that narrow and unique set of inputs. These inputs may include anecdotal evidence and fallacious perceptions.[1]

Sometimes we think the only information…

Even though I can’t fully prepare you for what’s coming, I hope my experiences will shed some light on parts of the process I found surprising and provide some useful context along the way.

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Originally posted to the Orbit Blog.

I knew fundraising would be hard — everyone said so. But despite all the advice I received, I wasn’t fully prepared for the emotional and intellectual challenges we experienced over the 12-week period from our first angel meeting to closing the round.

Events and emotions moved quickly, and we had our fair share of disappointments, but we met some amazing people, learned lots about investor psychology, and felt all the feelings.

In the interest of sharing my learning (which is a practice we keep at Orbit), I’ve put together a few of my personal…

Use the “Turn & Tell It Test”

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One of the main criteria for assessing your brand is to ask yourself, Does this actually matter?You can have witty headlines, stunning graphics, and super helpful micro-copy, but if what you’re saying isn’t relevant, you’ll dilute your message, confuse your audience, and fail to convert with your marketing.

So why is it difficult for founders to create and evaluate high-impact messaging?

One reason is the risk that threatens any type of creative process: you get so excited about the output that you don’t know if the output is actually any good.

In Jurassic Park (the original version), Dr. …

The step-by-step guide for startups, with tools & examples

From the earliest stages of a company, it’s important to understand the competition. If you don’t know what’s already in the market, you might build a me-too product with similar features and a copy-cat brand. On the other hand, insight into the existing solutions and their positioning will provide you with a foundation for differentiation and powerful storytelling.

Whether there are 6 other people building the thing you want to build, or zero, your offering will be influenced by what’s in the market. But managing all that information can be tough.

To help founders conduct this process, I’ve developed an…

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“white ceramic mug beside orange pencil on open book page” by Shirley Tittermary on Unsplash

The Brand Strategy Canvas removes the guesswork from developing a brand strategy. Here are a handful of tips that will help your team get the most of the Canvas.

Garbage in, garbage out

Like any process, the tool itself useless without deliberate and thoughtful effort. Done casually, the canvas could be completed in as little as 5 minutes. But it’s not a race. If you want results that are true and actionable, you and your team must be willing to ask hard questions, push your assumptions, and move past the obvious.

Work alone

Startups are naturally collaborative, so the tendency will be for everyone to work…

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I’ve worked for two startups and consulted & advised many more, and across all that experience, I’ve noticed one consistent theme: startup branding is hard.

Every founder has to do it, but they don’t teach it in school. Online guides are too high-level to be helpful, and on top of that, the vocabulary of brand is esoteric and inconsistent, making it difficult to share ideas and best practices.

Compared to the more objective and data-driven aspects of building a startup, it’s no wonder branding seems like a dark art to many founders.

To make matters worse, Google “startup branding” and…

Founders must define their startup’s brand positioning, or someone else will

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Photo by Zach Reiner on Unsplash

You know what your company is all about: your vision and values, your mission, and all the ways you’re different, the impact of your products.

But does your audience?

I bet you think so.

But what if you asked them? Better, what if you asked their friends? Across how many hops would your message stay intact? Without clarity and focus, the fidelity of a company’s messaging degrades quickly, leading to brand drift.

Brand drift is when the mix of customers, competitors, and the market define you, rather than you defining yourself.

Brand drift is bad for several reasons:

  • you spend…

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Photo by Dan Gold on Unsplash

“Brand strategy” is important for startups, but the concept can feel abstract for many founders. My favorite way of making brand strategy actionable is to boil it down to a positioning statement.

A positioning statement distills all the research, insight, and context of a strategy into a a single sentence that becomes the foundation for your design and copy.

Of all the things you could say, what should you say?

You probably know what to say. This is your vision, mission, what makes your product special and effective.

A positioning statement helps you determine how to say it most effectively.

The statement incorporates several elements of a brand strategy (this structure…

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Photo by rawpixel on Unsplash

Startups have to write a lot, especially those in B2B categories. Cranking out blog posts, product launches, and various types of emails is tough. In the whirlwind of deadlines and KPIs, it’s easy to lose sight of the people on the other side of those emails.

When that happens, you find yourself on the slippery slope of brand narcissism, losing all touch with customer empathy.

But effective writing is customer-centric and helps to answer the So What? of your business. The problem is that much B2B writing is self-centered and doesn’t help customers view themselves in the company’s narrative.


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Photo by prottoy hassan on Unsplash

Are these cognitive biases impacting your team’s performance?

In customer success, we talk frequently about tips for onboarding customers and ideas for preventing churn, but as the field matures, I think it’s important to begin unpacking the underlying drivers of longterm success.

I believe that critical thinking is a core competency for successful CS teams, but that the cognitive bias stands in the way of one’s ability to think critically. Bias shades one’s own thinking while impacting a team’s ability to move ideas forward. The challenge is that while biases are frequently present, they’re usually hard to identify and mitigate. But here’s the good news:

Understanding bias is…

Patrick Woods

Founder and CEO of Orbit, the CRM for Developer and Technical communities. Signup at

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