A step-by-step actionable breakdown for first-time founders.

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Thanks to Chris Liverani for the image.

Launching a B2B startup is fraught with distinct challenges. Chief among them is defining, approaching, and closing your first set of customers.

This cohort provides a foundation to test, iterate, and substantiate your product and go-to-market hypotheses.

Or, maybe you’ll pivot and find a new direction as a result of your learnings from shipping and supporting a product actively in the marketplace.

I’ve experienced both scenarios personally and built successful B2B companies from them.

Either way, achieving this is a complete game-changer for your startup.

You’ll have a client base to build exponentially upon, and, greater leverage to hire amazingly talented people or close investment. …

From Call of Duty player to machine learning influencer.

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Image supplied by author.

I don’t know about you, but when I was a teenager I wasn’t doing anything exceptionally productive.

Mostly playing video games online and listening to a lot of rock and heavy metal bands.

So, when I recently stumbled upon 16-year-old Pratham Prasoon on Twitter, he caught my attention.

Over a period of a few months Pratham went from being a passive consumer of Twitter content — with just a handful of followers — to an influencer with 40,000+.

And, this wasn’t an audience centred around TikTok memes or another content genre you’d expect a teenager to tweet about, like esports.

It was machine learning — a really hot topic in the tech community that’s pretty hard to break into as a voice. …

Advice from founders who got investment, Mark Cuban himself, and my personal experience.

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Image supplied by author.

It’s no secret Mark Cuban welcomes entrepreneurs to pitch him via cold email.

As a self-confessed “grinder at heart” he appreciates the hustle and regularly makes investments in founders who send them.

With a pretty broad appetite across many industries and funding-stages, the founder of Broadcast.com and current Dallas Mavericks owner attracts all kinds of proposals.

Interestingly, sometimes he ‘cuts a check’ without even speaking to founders outside of an email exchange — it’s the most efficient use of his time.

On the occasions where he’s not “fully versed” on a particular market, someone in his team (with appropriate expertise) will pitch in to scrutinize the opportunity. …

One said he needed a “psychiatric examination”.

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Thanks to Couleur for the image.

Raising money to explore an idea is tough. Particularly if you are a first time “unproven” entrepreneur in that market or industry.

Founders often have to “go the extra mile” to convince investors they have a business model worth pursuing and the talent to make it happen.

Common ways of demonstrating this are to hire “rockstar” co-founders who inject a ton of credibility into the venture, or, by building and shipping a basic product that “validates” a hypothesis. Preferably, both.

In other scenarios, putting together a “prototype” which conveys the business and product vision helps a ton.

One of my favorite stories in this regard is that of Steven Schussler. It’s “wild” in multiple senses of the word. …

One promotion was totally “saucy”.

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Thanks to Creative Exchange for the image.

I was recently emailing Jesper Buch, founder of Just Eat, in relation to another subject I was writing about. The company is publicly traded and worth many billions of dollars.

As a direct result I learned about how he and other members of the Just Eat team acquired customers in the early days.

With a marketing budget of approximately zero, they managed to signup thousands of paying customers onto their platform from scratch.

Achieving that was absolutely pivotal in generating the momentum needed to build what would eventually become a multi-billion dollar business.

Fascinatingly, this customer adoption was driven by tenacious “real world” marketing initiatives such as pitching people face-to-face, decals, and events. …

Celebrities were “harmed” in the making of this story.

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Background from Ryan Cryar

It was late 2009. I was working in a corporate banking job and had just launched my first ever product online as a “side hustle”.

It was a “social polling” network called WhatPoll?

Basically, a website where you could vote up or down on things in lists about movies, restaurants, historical facts, etc and “debate” the merits with others.

The idea was to build up an engaged community and then monetize via advertising and affiliate partners.

I had spent the previous year reading a ton of literature about building Internet businesses and companies in general — search engine optimization, landing page optimization, guerilla marketing, “how they got started” stories, etc. …

It led to me shelving a lot of projects.

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Thanks to lehandross for the image.

One of the first things I do after “stumbling across” a new B2C business idea is to run some “back of the envelope” calculations to get a sense of whether or not it has a realistic path for growth and or profitability.

At such an early stage it can feel futile to start modelling financials like this. There are a lot of unknowns, so projections rarely materialise in reality.

Frankly, this is something I agree with.

Forecasting exact figures over a period of years and attempting to draw meaning from them is largely fruitless — it creates an arbitrary financial roadmap. …

How do you measure up?

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Thanks to Charles Deluvio for the image.

Let’s make one thing clear, upfront.

There’s no “silver bullet” when it comes to signing new customers. It’s mostly the culmination of great product and process.

But, there are certain mechanisms you can use to materially improve your likelihood of closing a target customer.

One of the first things you have to consider is that it’s not just the companies in your immediate market that are your competition.

Your prospect has limited bandwidth to onboard new suppliers each quarter — time, cognitive energy, integration costs, budget constraints, etc.

Essentially, you’re competing against every other company pitching them.

Your prospect will prioritize signing with suppliers in order of those that deliver the greatest return on investment in meaningful areas. …

“If you’re good at something, never do it for free.”

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Thanks to BROTE Studio for the image.

A fairly common mistake first-time B2B founders make is offering their newly built product or service for free as a mechanism to onboard a first set of customers.

There are exceptions, but, generally speaking, this is a bad idea.

I know why this approach comes to mind. I’ve been there myself and faced the same internal conflict.

Since your reading this, I’m going to assume you've had the same thoughts.

When you’re starting out as a B2B founder you psychologically undermine your own position.

The companies you want to pitch are successful, professional, and polished.

Meanwhile, you’re a “chaotic” and scrappy team of 1–4, maybe working part-time outside of your “day jobs”. …

And, how it worked out.

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Thanks to Karolina Grabowska for the image.

Raising a seed round is part of the established narrative for early-stage startups.

It feels like the beaten path. That you are an outlier or “unendorsed” in your mission by not going down that route.

This is partly because fundraising announcements make juicy headlines.

The opposite is not so true. Well, until a “bootstrapped” business grows to the size of MailChimp with $700m+ in revenue.

Then, it becomes a story.

At my second startup, which was a B2B AdTech business, we quickly reached a “crossroads” moment.

It came to a point where we had to make a quick decision about whether to raise a seed round or push on under “our own steam”. …


Martin Delaney

I write about the “hustle” of entrepreneurship and building startups. Founder for 10+ years (sold 2 companies). Reach me here: martin@foundershustle.net

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