Everyone is killing it, except when they aren't, and there's a good chance you'll never know.

I get a lot of criticism from people about how open I can be. Ever since I was a little kid I never understood why we would constantly spin our lives to make it look better than it was.

When I was working for a production company a few years back we were getting our ass kicked. It wasn't because of us, or our work, or our clients, but because the market was crumbling. Everyone had a camera and marketing directors were assuming great work just happened. 

I would go to meeting with peers around the city and the story was always the same. 'We're killing it!' And when I asked how they were doing it, some of their answers were clearly demonstrating they were, but a bunch was superficial. 

This style of conversation continued for me as I started this business and became more entrenched in the startup community. I understand it's not appropriate to go around and tell everyone and anyone about your problems, but I also feel like we're doing a poor job of being honest with each other.

There were a few months when I first started this company that I felt 100% like a failure. I had great clients, was writing every day, was making money, but I wasn't 'killing it,' the way I thought everyone else was. 

I decided to reach out and ask for help. I called on coaches, and consultants, and educators and asked how they did it. My questions weren't soft. In fact, they were probably more invasive than most were used to. But I needed to know, what was I doing wrong?

And that's when I realized we were more or less all in the same boat. Sure some folks were ten plus years ahead of me and had built a stable funnel of clients and were able to project out more than a few months, but most of us were all worried about the same things--Losing our biggest client, losing our edge, wondering if our advice was really worth the money we were asking for, etc.

For someone starting out, it was more empowering than deflating. I knew I wasn't alone and that my perspective of 'killing it,' wasn't necessarily what was happening.

Which brings me to this post today. If you're starting a business, in the middle of building a multi-million dollar company or just went public, don't forget everyone around you isn't killing it. Heck, I"m sure a lot are just hanging on. The trick for us as leaders is to figure out who to reveal our thoughts, without disrupting the system in place. We don't want to sabotage our own business or reputation, but we also want to be open enough that we can have conversations about the hard things. 

Which is why, when someone asks me how it's going, I'm usually answering: It's great for the spot I'm in right now. I wish there were some other things that were happening, but I realize it's a journey." And it's there that usually someone will bite and we'll go from 'life is so good I just booked a trip to Ibiza' to a real conversation that we both benefit from.

Upcoming Workshops

Curious about how to be a better storyteller? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.

 

Startup Storytelling: Part 2 - Understanding Perspective

Part 2: Perspective

When you're starting to think about your startup story and your pitch deck, it's important to think about the different ways you can use perspective to convey your points. When working with founders, I like to start with focusing on three main perspectives they will use.

I vs We vs They

I - Great for when you need to tell a personal story or move the audience through your own self-awareness. This is a great way to frame origin stories, stories of conflict and how to overcome them, and mentor stories.

We - For early stage startups, the ‘we’ usually applies to the early adopters, investors, partners and employees. Use ‘we’ when you’re talking about the journey from a group perspective. One great way to use it is by transitioning from ‘I’ during an origin story, to ‘we’ as you talk about where you’re going.

They - Great for times when you want to name the villain or point out some- thing that you and your team is not a part of. Stories many times include the struggle between good and evil, and by using ‘they,’ you can make sure your audience fully understands the context.

As someone who is dyslexic I constantly switch between perspectives without realizing it. IT works okay in conversation, but when I write, it can derail what I'm trying to say and make me look as if I don't clearly understand the subject.

If you can, when you're listening to founders speak, pay attention to the perspective they use and how it makes you feel. Specifically watch how they switch from different perspectives to highlight a point, or anchor a story.

Today's Exercise

Take a moment and think about where you are in your business lifetime and what perspective you are using the most when talking about it. Once you've identified if you're a I, We, or They, person, think about how you could integrate other perspective to help you achieve your goals. And then go out and try to see what happens when you use it in real life.

Upcoming Workshops

Want to learn more? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.

 

 

Startup Storytelling: How To Get Started Telling Your Story

Over the next few weeks I plan to write a series of posts that are aimed to help business leaders develop, format, and design startup story. Once I've got them all together, I'll format them into a PDF for easily consumption. Until then, just go back in the blog to start from the beginning.

Part 1: Getting Started

It is no secret that founders have too much to do and not enough time to get everything done. Spend time with just about any startup and the phrases ‘fail fast and fail often,’ ‘nothing has to be perfect, just ship it,’ and ‘I’m winging this presentation’ are likely to come up.

While there is some merit to this, don’t assume your story and pitch deck will just happen. In my opinion startups are built on three things:

1. Identifying a problem
2. Creating a solution
3. Communicating your vision to the audiences that matter

Founders spend a lot of time on the rst two but often leave the third to chance.

My goal with these posts are not to slow down the speed at which you build your business, but to make sure you build the foundation you need for a long-term narrative and consistent story arc.

The stories you tell early investors and employees will change as the business evolves, but the core of those stories should remain the same.

And these stories can do some great things for your business including:

  • Finding the right investors faster

  • Helping you recruit mentors

  • Signing up early partners and customers

  • Recruiting and hire top talent

  • Galvanizing your team during times of struggle

Before we jump into starting your story, lets take a brief moment and highlight a few of the elements a great story has. If you can include as many of these in your overall business story, there's a good chance you'll be more likely to succeed.

  • Something happens

  • A clear point

  • Relatable

  • Appropriate for the audience

  • Includes details

  • Well paced

  • Con ict

  • Practiced

  • Can be retold by the audience fairly easily

Which now leads us to the first exercise in this series. Figuring out from the start what you want to accomplish and why it matters.  So take a few and answer the questions below. First drafts are great, but don't overlook the power of letting it marinate a bit. 

Exercise Questions

In a perfect world, what does the story you're trying to tell do for you and the business?

Why is this the best story to tell right now?

Are you building off a currently crafted story? Or are you starting from scratch? 

Where do you feel this story needs the most help?

How will you determine when your story is ready for an audience? 

Upcoming Workshops

Want to learn more? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.

Why Reps Matter When It Comes To Storytelling

Two weeks ago while on a family trip to Winter Park, my wife introduced Angela Duckworth's new book Grit to me. If you haven't read it, the short, short, short summary is: Grit is one of the most consistent ways to tell if someone is going to be successful in whatever endevor they choose.

While the book is well worth a read, for the sake of today's post, I'm going to focus in on some themes around the power of reps and persistence. Similar to Malcom Gladwell's 10,000 hour rule, Duckworth spends time on the transition between natural-born skill, learned skill and developed skill.  

While I was reading it, I thought back to all my friends who were natural writers and how it felt when I would be graded on a curve with them. They could literally sleep in, write the paper two hours before class, and still kick my ass. My paper on the other hand took forever to write. And it wasn't because I wasn't naturally talented per se, but it was because I didn't have enough writing under my belt to quickly structure and formulate my thoughts.

As time progressed however, I found myself starting to compete more and more for the top end of the curve and eventually I got a few high marks on my paper. (Very few though. Very few)

And it is the same thing for anyone learning how to tell a story, let alone their story. Just think about it. When you're starting out as a leader in your career, you're figuring out how to make the transition from rockstar, to a leader of many who's cumulative success is now your success.

The story you're used to telling -- look at me and what I'm capable of -- turns into more of a story about 'look at us, and what we are capable of.' In the immediate the story seems similar and many parts are,  but the more and more the leader tells it, the more it changes and morphs into a new story that redefines who they are and leads people to the action.

In business these transitions can be expected to happen quickly. Almost over night in fact, but the fact is they need time to work their way out.

Which is where we come back to Grit. One of the things I loved most about Duckworth's philosophy is that once a skill has been learned, it's through experience that the person with the skill becomes a master. 

She also discusses that the degree of growth slows down as more and more time is invested. She writes a lot about how athletes practice intentionally on small skills that they spend thousands of hours to hone. They do this after they have the basic ability to be good, but need to refine how to be great.  

And then that's when it struck me: This is my 80 / 15 / 5 rule. When creating a story it's easy to get 80% of the way there. Most of the time that's where people stop in fact. The next 15% can take 2-3X the time it took to get to the first 80%, and it can feel like it doesn't make a huge difference. Then there's the last 5% which can be 5-10x the amount of time if not more than the first 95% all together. And this is where you find people like Steve Jobs.

So don't forget that if you're trying to pitch your company, be a better leader, or make the transition from employee to leader, to give yourself time to learn and refine your story. Because if you don't, you'll never fully get to where you want to be and you'll be trapped in the 80% forever.

Upcoming Workshops

Want to learn more? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.

Ira Glass on Storytelling & Why It Matters To Business Leaders

If you haven't seen Ira Glass's phenomenal two minute talk on storytelling take a second and check it out. I'll wait while you watch it below.

I can't remember how many times I watched this video over the last several years, but it has to be at least 50. I turn to it when things feel like they just aren't quite working. Or when I need a reminder that even though the work I'm doing isn't where I want it to be, I need to trust the process and keep on going.I also have every business leader I work with watch it as well. 

For the sake of this bit of writing let's break a few key parts of his philosophy apart and apply them to the business world.

 

"Nobody tells beginners that there is a gap and the first few years when you're making stuff, the stuff you're making isn't so good."

This isn't going to be popular, but it needs to be said. Too many founders, VC's, speech coaches and accelerator networks take the approach that storytelling is something that should be natural for the founder. Who better to know and tell the story anyhow? Obviously the founder needs to be able to articulate their story, but that doesn't mean they'll know how to do a good job right off the back.

Which is where things come off the rails. Founders are just like every other storyteller, they're figuring it out as they go. A seasoned business leader who has been studying and telling stories for decades usually can shorten the gap between starting a new story and having one that is ready for primetime, but new founders need time to breathe and the understanding that it's okay if the first few hundred iterations don't work.

 

"Your Taste is Still Killer"

This is one of the hardest things for any storyteller and communicator that has good taste. It's maddening when what you're trying to say/do isn't reaching your taste and people around you are giving feedback. I remember the first time I got edited early in my career for a newspaper story and it felt like I'd never be able to write a sentence again. I knew what was good, but my work got ripped apart and I suddenly got doubtful. 

If you're a business leader don't overlook this. It's good to watch TED Talks, and product launches by Steve Jobs, but don't forget those folks had this same problem you do. Keep focus on your taste and keep going.

 

"A lot of people never get past that point. A lot of people quit."

This is hands down what separates the master storytellers from everyone else. It is also what separates CEO's that can galvanize workforces and move the business into the stratosphere. And it's easily the most hard thing to do. 

If you're a leader, give yourself the time to let this process work its way out. Know that you're most likely not going to go up on stage and knock your first pitch out of the park. Or be able to effectively communicate down the ladder in a large organization. 

This is also a great place to watch this clip a few times. In fact, bookmark it.

 

"Do A Lot of Work"

There is a lot more we could talk about but I'm going to leave this right here. It's the cornerstone of this whole post. The only way to get better as a storyteller is to tell a lot of stories. There is no way around it. 

There are some hacks including hiring professional coaches, but they aren't the full answer to the problem. In fact, if you do hire a coach, grill them. Don't assume just because they say they are a storyteller they really are. The fact is they might sound super smart at first because they know formulas to put your story together, but under the hood it falls apart quickly.

I'll be the first to admit I'm not always the right fit for people and that's okay. Don't think just because you hire someone you can skip the work. 

 

Upcoming Workshops

Want to learn more? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.

Starting a Business? Don't Fall Into These Pitch Deck Traps

I spend a lot of time with entrepreneurs who have either raised a seed round and are going for a Series A, or are starting from scratch and need a few hundred thousand to get things rolling. 

While I love their energy and drive, I'm constantly frustrated by the stories they try to tell. It is not that the stories are bad, or don't matter, but it's that the stories are usually for one audience only: The VC.

Here's where I see things going off the rails.

About Where They Are Going In 5 Years, Not What Is The Next Step

Every business it seems is a billion dollar business at some point. Every market is so massive that if the startup captures 1% of 1% they still make millions. And while it might be true, I rarely hear founders talking about the next step they need to take to get there. Don't get me wrong, I love the big picture story and the hutzpah it takes to stake a flag in the ground and ask people to wonder 'what if,' but it's not the only story founders should be focusing on.  

"VC's Don't Get It Because They Don't Understand It"

Hands down one of the most common phrases I hear. My typical response is, 'so what don't they understand,' which usually comes back with 'everything.' Then after a few more questions we're able to narrow it down and start working. The reality is, most times founders forget that they've been thinking about their story and business for hundreds, if not thousands of hours, and their audience most likely has been thinking about it for a few minutes before they pitch. Falling into the trap of 'they don't understand it,' is a valid point, but can also be a copout. If this is happening to you, make sure to ask detailed questions to find out what exactly they don't understand and then work to change that in your pitch.

"Trust Me, It's Going To Work."

This works in the movies. Specifically Die Hard, but for the majority of us, this shouldn't be coming out of our mouths. But it does, and usually it's as an exclamation point after a big sweeping statement was made. Don't get me wrong, if you're a founder who knows how to use comedy this can be gold, but too many times the founder actually means it. Storytelling, especially storytelling during the early stages of business, is about suspending belief and instilling confidence, and while this line can work, it can't be the anchor of your story. If you're going to use it, have the next graph be about what you can control to make sure it works. Use this less as boasting and positioning, and more as self awareness and confidence.

"This Is Hard."

Yes. Yes it is. It's insanely hard actually. And as I mentioned yesterday, it's also a never ending process. Embrace it. Don't fall victim to the trap of never having confidence in your story, but also don't fall into the trap that every audience is the same and it's a one-and-done process. If you're trying to craft your story, start here: Get away from the people you know and hear feedback from those who don't have skin in the game with you. Also, don't ask someone who isn't your target audience their opinion until you've asked your audience. The person at Starbucks might let you buy them a drink and listen to the pitch, but they also might be 100% opposite of who you're trying to sell to. 

Upcoming Workshops

Want to learn more? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.

Your NeverEnding Story

One of the most common things I'm asked during presentations and one-on-one engagements is 'when do I know my story is done?' It's a valid question, at some point the story you're creating does need to have some sort of finality, but it's also a trap.

We live in a culture that wants to move fast and break things. Failing is all the rage and pivoting means hard decisions were made. In the startup word this type of behavior is celebrated and CEO's love to talk about it during panels that highlight their origin stories. The bigger problem is this mentality spreads into everything else, including the need to 'hack our story,' and create a pitch deck that wins investors, but takes little time to create. 

I don't want to sound like a curmudgeon here. There's a lot of validity to this type of thinking and many businesses who aren't able to do fail fast and pivot fall apart, but the reality is it doesn't work for everything. And that especially means your story.

The reality is your story is never finished. It's a living organism that morphs into different shapes depending on where you are in your life and what you're hoping your story will do for you. When you're starting a business your story is a daily, if not hourly, iterative process. One day you might be talking about the potential of signing a big partner, and the next day you're shifting to how the partnership is going to need to take resources and vision to pull off.

There's this idea that investors want something that's canned, yet also care about the story more than the numbers. Almost all the pitch decks I see, and some of the ones I help create, have a similar formula and arc to them, and while it's necessary, it's also frustrating. 

The approach I find from many founders is 'just squeeze it in there and I'll figure out how to explain it later.' Which needs to happen at some level, but isn't the way a master storyteller works. The magic of a story is in the understood nuance of the narrative and emotions that are embedded sometimes obviously and sometimes subconsciously.

So if you're trying to figure out your story, or tell the story of your business, give yourself a bit of a break and don't try to write the next great American novel. Think about where you're story is at today, where you want it to go, and how that narrative can be told with room to expand.

And give yourself time. There is no way to hack this. It is easy for some to get 80% of the way there, but that last 5%, the part that makes it stand out and people notice, is usually 2x the work for the first 95%. 

Upcoming Workshops

Want to learn more? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.

Four key takeaways from my time with Boomtown Accelerator's latest class

I got the chance to work with Boomtown Accelerator's latest class over the past five weeks and it has been nothing but phenomenal. 

Each of the eleven teams are doing something interesting, and every founder has a fantastic backstory to boot. 

My work was focused specifically on startup storytelling, and while I didn't spend a ton of time with each time, I was able to help each team craft their mentor pitch and prepare the rough story arc for their pitch, which will be happening in seven or so weeks. 

Here's four key things that stuck out:

One: The self awareness of the founders was impressive. Nobody was cocky. Nobody told me they figured it all out. When I worked with each founder to help edit their pitch they were receptive and wanted to push themselves past good enough. They weren't guarded, or narrow minded, or shy to voice their opinion. It says a lot about what Boomtown is doing and the environment they're creating, but it also reminded me humility is not dead when it comes to early startups. 

Two: Storytelling isn't hard. What is hard is identifying what to say. Every team had fifteen different ways they could talk about their company and even more for their products. The challenge we had was identifying which one mattered, and then helping them put that into a story. If you're a founder you know this already, but if you're starting out don't get blinded by the sex of storytelling. That's the easy party. 

Three: AI is huge and it is still super hard to explain. Like VR, AI makes sense to some, conjures up bad images for others, and just confuses the heck out of most. There's two different AI teams and they both are having some trouble figuring out how to frame their product. I'm not sure how they'll do it, but come demo night it should be interesting. 

Four: Everybody is trying to figure it out. Sounds cliche, and it probably is, but the reality is nobody has any real idea yet how it's all going to shake out during the first few weeks of the program. Some teams came in with a product and traction, while others were profitable and some just had an idea. Every team was engaged, willing to push themselves and in the span of a week they were changing ideas and implementing learnings. 

Startup accelerators aren't for everyone, but for founders who are a good fit, they can be pivotal to success. I'm looking forward to seeing how the teams progress and following up here with some thoughts on their pitches come demo night. 

How we measure the ROI of business storytelling

Measuring your return on investment is a big part of what we do at Rack Focus. 

Here's how we approach it.

Every business starts with clearly identifying what they think storytelling will help them achieve. We focus on current challenges, upcoming challenges, and where things are good.

Each of these segments then gets broken down into specific needs such as 'aligning sales teams and increasing sales,' 'improving employee engagement scores,' and 'aligning leaders with the current business strategy.'

From there we explore the ways strategic stories might help solve these problems. We aren't creating the stories yet, but we are starting to uncover what information needs to be included. 

A strategy forms from this process, and we begin implementation. For some goals we provide workshops, while other times we focus on individual projects as a consultant. Our goal is always the same: make sure you are telling the best story possible to the right audience. 

During and after our work, we help each business define a timeline and KPI's to track success. 

A great example of how this plays out is the work we did with Travelport's internal accelerator program. 

At the end of the program each team was required to give two pitches. The first was towards investors and needed to show how their business was just not a cool business, but a fundable opportunity. 

The second was to a public audience at the closing night party. 

We identified what each pitch needed to do, how to structure each need, and how to roll that into the weekly cadence already in use by the program.

We had weekly check-ins to monitor teams' progress, and as we got closer to demo day, we did one-on-one coaching.

The end result was a series of pitches that exceeded expectations and also attracted some seed funding.  

To learn more about the work we do and how we can help your company contact us here

It is not about storytelling. It is about communication.

Two weeks ago (over a phenomenal bowl of noodles) in Denver's rising LoDo neighborhood, I overheard two founders talking about their fundraising efforts. 

The founder to my immediate left had just botched a pitch and was frustrated that the VC's weren't seeing what was so clearly an obvious investment. 

His partner, sitting across the table and trying hard to be supportive, suggested maybe the story was wrong. Were they telling the right stories to investors?

I thought he could be right, but I also wondered if the businesses just wasn't sound. 

Either way, the interaction was an example something that I'm hearing more of today:

Storytelling is the simple fix to getting what you want. 

Except it's not. 

When working with organizations I make sure to be up front that at its core, storytelling is about communication. It just so happens it's one of the most effective ways to communicate, but it's not the only way to communicate, and sometimes it might not be the most effective. 

Workshops start first with identifying what each team member is trying to communicate, and then helping them look at different story structures that could help them. 

Everyone from the C-suite to the newest JR hire needs to communicate, and if an organization is full of strong communicators, the bottom line is sure to show that. 

The trick, though, isn't finding time for a workshop, but making sure that what's learned continues to be used well after the lights are turned off. 

What we have found is that communication is like any learned skill -- it needs to be done over and over before it comes naturally. Providing employees with the chance to to practice is important if your company is going to reap the benefits.