Bootstrapping Sales: Philosophy

Having a philosophy with purpose is essential to success and happiness in any relationship. Your Sales initiative is not exempt from this. Think of the Philosophy installment of Bootstrapping Sales as the operating system on which a sales machine can be built.

Nima and I developed this section of Bootstrapping Sales from successes, failures, wounds, and wins, and we boiled it down into five key concepts. I’ll explain each concept, why it’s important, and how to use it.

One piece of advice before diving in:

Bootstrapping Sales is about being directionally correct with your sales strategy and execution. Don’t get stuck in the mud with too many minute details. Traction will come from taking action and you guessed it, being directionally correct.

1. Hustle & Persistence

These terms get tossed around so much that it may seem obtuse to list them for folks looking to bootstrap sales. Unfortunately, it’s not.

To sell a product for the first time takes a crazy amount of effort. An individual quite literally has to create something from nothing. You will have to hustle your face off to make that sale happen. But what does hustling your face off actually mean?

It means making enough calls, sending enough emails/InMails/tweets/smoke signals/hand written notes tied to pigeon legs to give yourself a chance to reach an actual decision maker (note: not gatekeepers!). Then when you reach one, you’ll need to convince them why your brand new product or service is oxygen to their organization. So yes, it’s hard!

Established companies convert new business at a rate of 4% to 12% in their given sales cycles. For example, at one point at Groupon, new business conversion for local deals in North America was ~4.5% in a 90 day sales cycle.

But if no one has heard of your brand and you’re not an established company, I like to give the low end of that conversion a healthy 2/3rds discount and assume converting at 1.5%. Effectively, I need to close one out of every 67 leads contacted.

Fundamentally, if I can’t convert one of every 67 (!!) businesses then there is likely one or more of three things happening:

1. Product sucks - fancier people call this no ‘product-market-fit’
2. Selling to the wrong people and/or the wrong channels
3. Pitch sucks

Let’s dig further into the numbers: say the costs of running your company is $5k/month ($60k/year). This is your salary, server costs, contractors, etc. To make this simple, assume no cofounders or employees.

If you sell your product/service for $1000 per year, you need to close five deals per month. That means you need 335 (5 x 67) leads per month that are in your zone and you need to contact them all each month. Assume five touch points to close a lead (note: one-call closes happen once-in-a-never), then you need to send 1,675 touch points each month. Assuming 22 weekdays in a month, that’s 76 per day.

So don’t kid yourself — that type of effort takes hustle and persistence, but it does not have to be hard. Be methodical. Break your contacts each day into groups of 10. Do ‘call blocks,’ 10 at a time. Give yourself a break. Do some burpees, high-knees, and butt-kicks. Send your spouse a loving emoji. Call your pops. Then get back to the next ‘call block.’

Hustle, be persistent, and you’ll start closing sooner than you think. Believe.

2. Sales is not for you

Your customer does not care what internal forces drive your company. They do not care if an investor wants your company to grow 100x or if your sales leader closes a $2M deal, and they certainly couldn’t care less about the fact that your startup won’t exist in five months if you don’t close XX deals at YY margin. Apologies for the run-on sentence — needed to drill in point.

What does the customer care about? They care about themselves. They care about their career, and their family and friends, and just like you (and me) they care about their Twitter likes :)

So guess what your job is? Your job is to care about that too. I mean truly care. I often return to this quote from the now-cliche-but-always-epic Dale Carnegie when viewing prospect cold calls through the Bootstrapping Sales lens:

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”

It’s dead-set, spot on. Start caring about your prospects, and then they’ll start caring about you.

Lucky for you, this concept takes minimal effort. We live in a world where if you’d like to get to know someone, you can find pretty much everything you need to know about them in 5–10 clicks. Here’s the process to follow, without paying for a service:

1. Ahead of speaking with any prospect, Google their name, pull up their LinkedIn, Facebook, Twitter, G+, articles, blogs, etc.
2. Spend five minutes jotting down notes on who they are based on what you learn
3. Visualize what they would look like if they were in front of you — often times, I’ll pull up a LinkedIn picture while I’m on a call
4. Take notes during the call*
5. Return to those notes on the next call**

*you do not need to pay for this — paper, Evernote, Gdocs are free

**again, while bootstrapping, you do not need a formal CRM, it just needs to be organized, and we’ll cover CRM in a future chapter

3. ABE to Build the Machine

ABE = Always Be Experimenting. Apply this mentality to everything.

You’ve likely come across the timeless sales acronym ABC. If not, watch the video in that link (it’s pure Alec Baldwin gold).

ABC may be the aspiration, but in reality Sales is in a constant state of flux. Further, and when you’re bootstrapping, down-is-up, left-is-right, and forward-is-sometimes-orange. It’s important to prepare to benefit from this volatility.

To best position yourself, start by writing down your sales process from scratch and track every single step you take as you move through your funnel. Doing this will give you an optimal environment to track experiments, iterate quickly, double down on what’s working, and cut loose what’s failing.

For future reference, we like to think of the steps in a sales funnel as follows:

Research → Lead Generation → Prospecting → Qualification → Opportunity → Win / Loss

We’ll cover every single of these steps in upcoming chapters.

4. Team Sport

Sales is the ultimate entire team sport. We developed this concept after watching too many startups silo off Sales from Product and other functions too early in their company lifecycle. This caused an internal combustion that tends to follow these four stages:

1. Sales questions why Product is building something that won’t sell
2. Product gets angry they didn’t know Sales wanted something
3. Product resents Sales for not coming to them earlier, shuts out Sales
4. Sales resents Product for shutting them off as well

Avoiding certain death needs to be the focus of the entire company while bootstrapping.

Ain’t nobody got time for small-team, cross-departmental caddy bs.

Here’s a few things to ensure the whole team is onboard the ship together:

1. Send out meeting notes to the whole team—include who attended the meeting and action items from the meeting. Create a space (e.g. slack channel) to host the notes as to not ping folks all day.
2. Have everyone on the product team listen to one sales cold call per week — up this to one per day if you want to get real fancy
3. Force the Sales and Product leaders to be friends by giving them time and space to hang outside of work — even if it takes a parental scolding once in a while

5. The Two A’s

The Two A’s stand for Attitude and Activity. Attitude doesn’t come from a sales win or even a professional sales organization at all. While working as a counselor at an overnight summer camp in Webster, Wisconsin, I learned a set of guiding principles on how to act in front of campers to ensure they experienced the hashtag-best-summer-of-their-lives. One of the core tenets was a concept called Choose Your Attitude. It explained that every staff member was responsible for their own attitude, so choose a positive one for the campers to emulate.

Next comes Activity. Activity comes directly from someone who had a mega-impact on the early part of my sales career: Mr. Darren Schwartz. Darren is an every-superlative-in-one type of sales leader. He grew Groupon’s sales team from 40 to over 800, helping the company grow into the fastest growing company, ever. On the second day of sales training at Groupon, Darren taught me a simple equation: skill X activity = success.

As a total n00b to sales, I took that to mean I could be the worst salesperson in the world, but if I called and emailed enough people (manually of course, pre-yesware/reply app era), I’d eventually sell something. I set out to be at the top of the call charts every day, even when my skill improved to parity. I ended up being one of the top sellers at Groupon in a few months.

We’ve combined these two to use at any perceived obstacle. Here’s how to apply The Two A’s to any challenge while bootstrapping. Ask yourself:

1. Attitude — is the way I am thinking and/or feeling towards my current challenge truly productive?
2. Activity — have I given myself (or my process or my team) the best opportunity to truly succeed?

Be ferociously honest with yourself, and if the answer is anything but FUCK YES, try again.

We wish you purpose, happiness, and success. Feel free to take these concepts and just like ABE: run your revenue engine through them, tweak them, and make them your own.

Want to Bootstrap Sales? Contact Danny for consulting help on bootstrapping or scaling Sales and Nima if you’ve been bootstrapping so far and are now considering raising capital from an investor.