We > I for Entrepreneurs

Over the last year I’ve had the opportunity to meet with dozens of entrepreneurs through the Endeavor program. At one of the events I was seated, listening to an amazing entrepreneur tell his story and it was incredibly compelling. Only, every 10th word was “I.”

“I grew sales 30% last quarter.”

“I acquired a competitor last year.”

“I hired an amazing executive.”

“I raised an institutional round.”

Finally, I interjected and asked, “Are you open to feedback?”

Curious, thinking what he had said wasn’t necessarily feedback oriented, I shared that his use of “I” was disappointing. He didn’t achieve those things by himself. He leads a team, not just himself.

Leaders need to say “we” and not “I”, especially when referencing organizational results.

“We” accomplished the goal.

“We” made it happen.

“We” > “I”, always.

Pushing Harder and Pulling Back as an Entrepreneur

Late in the original Pardot days we were having a constant internal battle around engineering. With the market growing fast, and competition fierce, there wasn’t enough time or resources to accomplish everything we wanted. Often, we’d push so hard on engineering — new features, bug fixes, removal of technical debt, etc. — that quality would start slipping and morale would drop. Then, belatedly, we’d realize we were pushing too hard and we’d have to pull back. Only, we’d pull back for too long and then be a little late ramping the intensity back up.

The pushing harder and pulling back as an entrepreneur never ends.

Eventually, we settled on an approach where we’d push hard one quarter on new feature development and crank out a ton of new functionality. Then, the following quarter, we’d pull back on the intensity of the team and focus on scalability, removing technical debt, and refining existing features. Product updates were always being pushed daily with continuous delivery but the internal approach would change each quarter with one pushing harder via longer hours and a greater focus on new features followed by the next quarter via slightly shorter hours and a greater focus on maintenance.

Morale, culture, and team dynamics are all things that seemed fuzzy and not important to me in the early years. Then, with time, the value became clear that these are major determinants why some teams win and others lose. Constantly oscillating between pushing harder and pulling back is part being an entrepreneur.

Entrepreneurs need to pay attention to the intensity within the organization and look for ways and strategies to proactively work the ebb and flow.

Startup Storytelling, Simple Pitches and 100 Words

Reflecting more on last week’s adventure at the amazing SaaStr Annual and Endeavor international selection panel, I noted that entrepreneurs, with all their enthusiasm and energy, have an opportunity to improve on their elevator pitch and storytelling.

The simplest, and most straightforward, elevator pitch is like a Mad Libs:

My company _________ helps businesses like _________ make more money by _________.

Pretty easy, right? Start with the company name, then add social proof via existing customers, and finally top it off by a brief explanation of the actual service.

Let’s look at an example:

My company Calendly helps businesses like LinkedIn and Zendesk make more money by scheduling meetings without the back-and-forth emails.

Now, there’s much more to the business, vision, etc. but the goal isn’t to share your life’s story. Rather, the goal is to assess interest, evaluate body language, and decide if it’s time to share more. With a positive nod and enthusiasm from the simple pitch, it’s time for the next step.

With the audience primed, it’s time for the 100 word story.

Warby Parker, a popular direct-to-consumer eyeglasses company tells their story in 100 words.

Once upon a time, a young man left his glasses on an airplane. He tried to buy new glasses. But new glasses were expensive. “Why is it so hard to buy stylish glasses without spending a fortune on them?” he wondered. He returned to school and told his friends. “We should start a company to sell amazing glasses for non-insane prices,” said one. “We should make shopping for glasses fun,” said another. “We should distribute a pair of glasses to someone in need for every paid sold”, said a third. Eureka! Warby Parker was born.

Share the origin story of the business.

Share the vision of the future.

Share what’s next.

But, most importantly, do this in 100 words. Something succinct. Something easily digestible. Too often, entrepreneurs take too much time and go into excruciating detail. Keep it light, fun, and memorable. Stories are memorable, details are not.

Take a few minutes, develop a simple pitch, a 100 word story, and align the team around it — think storytelling, not detail telling.

Scrappy First, Comfortable Financial Balance Later

Earlier this week I was talking to an entrepreneur that shared stories of a previous startup he’d joined a few years back. The now-removed leader of this previous company had a big-shot corporate executive background and was placed in this over-funded startup before it had product/market fit. As expected, their office was lavishly furnished, money was spent like they were already a profitable cash cow, and six months later the startup was bankrupt.

Boom, millions of dollars incinerated and nothing to show for it.

Starting lean and scrappy is an important part of the startup process.

When entrepreneurs raise a large round before a repeatable, scalable business model, most of the time bad things happen. Entrepreneurs are an optimistic bunch, so it’s only human nature to burn all the cash in 18 months, regardless of whether or not the business is working. When the cash is burned, and the business doesn’t make enough progress, investors are less likely to put in more cash, the cap table is often broken, and the startup usually ends in failure.

At Pardot, we never had institutional investors. From day one, we had to be scrappy — there was no other way. Every dollar we saved was a dollar to invest and grow the business. Even when we had over $10M in recurring revenue, Adam and I shared a hotel room on every trip. Little costs add up to big costs as the business scales.

Now, once the business model is working, there does come a time to ease up on the scrappiness — within reason, of course — and find a comfortable financial balance between spending too conservatively and being a spendthrift. But, like many things, as the financial purse strings are loosened, it becomes harder and harder to tighten them back.

Entrepreneurs would do well to ensure a scrappy, financially resourceful environment until a repeatable business model, and then slowly find a comfortable balance.

What are my strengths?

Recently an entrepreneur was asking me questions about my own entrepreneurial journey. He was interested in learning from other entrepreneurs and potentially modeling his style and actions after others. My advice: play to your own strengths. Only you can be you.

As for myself, I have a number of strengths and weaknesses.

I love starting things, but hate finishing them.

I love dreaming up ideas and getting others excited about them, but have little interest in the detailed execution.

I love connecting people and looking for ways to add value to others.

I love seeing trends in the world and guessing where things will be in the future.

I love finding gaps or opportunities in the market and thinking through potential solutions.

I love as little process as possible that ensures the organization is running well, but eschew anything that feels like overhead.

I love challenging people and working to help them grow in their careers.

I love getting doubted and then proving the skeptics wrong.

I love trying hard things and just move right along when most don’t work, with no regrets.

I have plenty of strengths and weaknesses, no different than anyone else.

My ability to see where markets are headed, recruit people for crazy ideas, and stay out of the weeds are some of my most important strengths.

What are your strengths?

Stories of an Entrepreneur’s Resourcefulness

Earlier this week I had the opportunity to hear Jewel Burks Solomon share her entrepreneurial journey and it was incredible. Reflecting on the Partpic story, the piece that stood out the most was her neverending resourcefulness. Setbacks, adversity, challenges — no match for her.

Within her journey, here are a few stories that stood out:

  • Jewel joined a company’s management training program and was assigned to run a call center. Only, on a daily basis she was bothered by angry customers needing to solve a problem — what’s the name and number for this part? She came up with an idea for a software product that analyzed a picture to determine the part. Yet, management at the company had no interest in pursuing her idea. Hence, the idea for Partpic — a computer-vision system for identifying parts — was born.
  • After investing her lifesavings in the idea, and running out of money, she started entering pitch competitions — anywhere and everywhere — as a way to fund the business. $250,000 and multiple pitch competition wins later, she had cash (bonus: it was mostly non-dilutive!).
  • When she decided to raise money, she pinpointed Joanne Wilson as her desired angel investor. Instead of approaching Joanne directly, she worked her network and met with several entrepreneurs Joanne had already invested in, and then asked them to intro her to Joanne in the same week. Joanne was the first angel investor.
  • Wanting to get on the radar of Amazon.com, she pointed out to the Amazon Web Services conference manager there weren’t enough women speakers, and she had just the person — her technical leader that was a machine learning expert. Amazon.com took her up the idea, her technical leader presented, and Amazon.com’s corporate development team was in the audience during the talk. After the talk, the corp dev team gave their business cards to the technical leader, who then gave the cards to Jewel. Jewel followed up and the rest is history — an acquisition by Amazon.com

Resourcefulness is one of the most important traits of successful entrepreneurs and Jewel’s story painted one of the most compelling pictures I’ve heard. Special thanks to Jewel for sharing her story and helping the next generation of entrepreneurs.

Frequent, Quality Communication as Success Indicator

Recently I was talking to a friend and he asked about indicators of entrepreneur success post investment. Now, pre-investment, entrepreneur personality traits like grit and resourcefulness come to mind, but after partnering with an entrepreneur, it’s a behavior that’s most indicative: frequent, quality communication.

Frequent, quality communication is an action, not a personality trait, and one that every entrepreneur can do. Only, too many entrepreneurs don’t do it.

So, if communication is an indicator of success, why don’t more entrepreneurs do it?

Easy, prioritization.

Many entrepreneurs simply don’t prioritize frequent, quality communication. To some, it’s beneath them — simply not worth their time. To others, they don’t understand the benefit.

Frequent, quality communication with all constituents — employees, investors, advisers, mentors partners — develops more clarity of thought and a vehicle for feedback and help. Just the act of communicating forces an articulation of position, strategy, and approach. More communication, more results.

Communication comes in many forms. Some of the most effective methods are the weekly update, simplified one page strategic plan, and daily check-ins.  Whether the communication is written, in-person, or virtual, it doesn’t matter. What matters is that it’s frequent and high quality.

Communicate early and often. Put in the effort. Make communication a priority.