
Rocket Ship Founder
By Steve August
Steve took his first startup from idea to successful multi-million dollar exit. He's seen the journey from two guys in a startup accelerator room to being CMO of a $100M+ 400 person global company reporting directly to a private equity board.

Rocket Ship FounderApr 20, 2023

Ep. 56 Permission To Trust Yourself Fully
Hi {{contact.first_name}},
My path to being a wise Founder Coach has been paved with mistakes. Let me list just a few with just my first startup:
Hired an expensive VP of Sales way too early and ended up laying them off within months
Didn't understand that I was building my business on customers that bought intermittently and required highly customized solutions
Waited too long to fire a a poisonous team member until they had poisoned many other team members
Pursued the shiny object savior silver bullet of the month/week/quarter instead of focusing on execution
Thought next product feature would magically cure sales problems (they didn't)
Didn't realize I needed a strong Type O - Organizational Maestro to balance out my strong Type V - Visionary Evangelist (and ADHD)
Didn't realize my service team was farming out work to contractors even when they weren't fully utilized, causing a huge operating loss.
Those are just the one's that are top of mind. And don't even get me started on the rest of my life, lol. Just this past week, I sent some USDC to crypto.com on a a chain they don't support for USDC. UGH. (Fortunately they were kind of enough to reverse the transaction - for a small fee).
The truth of Founder life is you end up fucking up a lot. You can accumulate a lot of evidence about how clueless you are about a lot of things.
It's enough to make you lose faith and trust in yourself.
But this is exactly why being a Founder is such an amazing platform for playing the Bigger Game: the game of you.
Because the Bigger Game in this Founder Journey is to fully trust yourself.
So how do you trust yourself deeply, fully even when there's evidence piling up that you are in over your head?
The first and most important thing is understand that it starts with giving yourself permission to trust yourself no matter what happens externally.
This week's Rocket Ship Founder Podcast is all about this idea of fully trusting yourself
In this episode, I cover:
Why giving yourself permission is hard
Where deep self trust really comes from
How to find it even in the midst of intense challenges
This 11-minute listen is offers some helpful wisdom for both business and life.
By the way the SlingShot
To your success!
Steve
P.S. When you are ready, here are 3 ways I can support you:
FREE Breakthrough Session Because you’ve made the time to take my quiz and tell me a little about you, I'm offering a free 30-minute Breakthrough Session. This is geared to Founders with at least $500k in Funding or Revenue to give you a legit breakthrough. In 30 minutes, we'll identify what's at the heart of your biggest issue and give you a plan to solve it. Book your session here.
Private Founder Coaching Sprint
My 4-month program specifically for Seed to Series A Founders with $2M+ of revenue or funding. In a four month sprint, we work hand-in-hand on accelerating your biggest issue. Beat overwhelm. Nail a thorny PMF/Sales problem. Level up as an operator. This is a space dedicated entirely to you. The only agenda is your success. Book a time to to connect.
The Sling Shot
This is my intimate and affordable Founder community, dedicated to helping earlier stage Founders win in business and in life. You get access to all my trainings, weekly coaching office hours and a group Slack Channel. Reply with "Sling Shot" to learn more.

Ep. 55 What NOT To Focus On
I'm back with this week's podcast episode after a little bout of COVID last week. All better now, so let's get to it!
One of the toughest things about the Founder journey is the overwhelm. There's so much coming at you all the time.
I was talking with a Founder this week who has been notified that their biggest customer is undergoing a serious re-organization. Their champion is leaving and it's likely revenue from this customer is going to dial down or even stop altogether.
There's no other single current customer or in the pipeline that's going to replace that revenue.
This Founder is starting at a big dent in revenue. It's likely they will have to make some gut wrenching team cuts if they don't patch this hole in revenue.
There appears to be a million things to figure out in trying to find that revenue. Plus figuring out the timing of the financial impacts and the hard decisions that may be coming.
This Founder understandably felt the overwhelm.
They antidote to overwhelm is focus. And focus comes down to two things:
Knowing which actions you can take that will MOST move you forward.
Knowing what NOT to focus on.
In my experience, knowing what NOT to focus is even more important than figuring out what to focus on.
Because it lets you block out all the noise and creates the necessary internal quiet to do your best work.
By the end of our session, we had boiled down this Founder's next right actions, relieved the overwhelm.
This week's Rocket Ship Founder Podcast is all about figuring out what NOT to focus on.
In this episode, I cover how to:
The 2 critical things you need to know get focused and beat overwhelm
Why all the available advice works against you
How to block out the noise and get quiet inside to do your best work
This 11-minute listen is offers some helpful wisdom for both business and life.
To your success!
Steve
PS When you are ready, I have one open spot to work one-on-one with me. If you're a Founder navigating the Seed to Series A journey who wants to:
Accelerate PMF and scalable sales
Build a high performing team
Step into a new level of confidence as a leader
Set up a time for a breakthrough session here.

Ep. 53 Overcoming Doubt & Exhaustion
Last week, I talked about the Founder journey being one of navigating crises, setbacks and fiascos, with some good wins thrown in to keep you going.
This week I want to address the inevitable companions to the journey: doubt and exhaustion.
These two words popped up a few times this week during my sessions with Founders.
I empathized in this moment as, despite a lot of effort and expense, our mysterious house air quality issues I spoke about last week continue without a clear resolution.
But the feelings of doubt and exhaustion also took me back to many different events when I was leading my first startup. We had a great sales quarter and I thought we had figured it out. The next quarter was downright crappy. We thought we had some good sales people, then they flamed out.
I knew my business could catch fire. But despite killing myself to make it happen, I couldn't see when and sometimes how it was going to happen.
The reality is this: there will be stretches in time when you're working full out and you're pouring your heart and soul into it - and yet your business isn't giving you the signal yet that you've nailed it.
During Seed Stage, you might have some early wins but they don't feel consistent. You don't know if they're the beginning of figuring it out or just you know some random positive noise that is positive noise.
And the thing is, you don't know in advance when you will figure it out.
Stay in this state for enough time, and that's when the doubt kicks in, aided and abetted by the exhaustion of the effort.
Yet during these stretches, you will have to keep working the problem.
So how do you stay centered and stable and energized without actually knowing if you've got it right?
This is one of the key aspects of The Bigger Game. Leveling up your ability to be solid in the discomfort of not knowing, while managing your self care.
This week's Rocket Ship Founder Podcast is dedicated to sharing the wisdom I've learned over the years to be good when the outcome is in doubt.
In this episode, I cover how to:
Manage your energy when you are working full out
Interpret early signals and move
To use curiosity to gain perspective and transform doubt
This 14-minute listen is offers some helpful wisdom for both business and life.
To your success!
Steve
PS When you are ready, I have one open spot to work one-on-one with me. If you're a Founder navigating the Seed to Series A journey who wants to:
Accelerate PMF and scalable sales
Build a high performing team
Step into a new level of confidence as a leader
Hit me up at steve@steveaugustcoaching and we'll set up a time for a breakthrough session.

Ep. 53 Fiascos, Setbacks and the Value of Surrender
Over the past few weeks, I've reconnected with that emotional roller coaster that I experienced when I was leading my first startup through Seed Stage.
Only this time it's more personal. I live in Portland, Oregon with my wonderful wife and awesome kid, and the two cats that they love, and I..um...tolerate.
We have a nice little house. It's been great for sixteen years. Until this year. This year has been a cascade of crises, fiascos, grinding effort and soul crushing defeats.
It started with a main water line leak that was spiking our water bills. Ok, get a plumber over to fix. Oops, plumber accidentally drills through our sewer line and we get sewer water backing up into our basement. Fiasco.
After that got fixed. Shingles came off the roof in a wind storm. Time for a new roof. Ugh.
Then last month, our kiddo, who has had really intense medical issues over the past four years, started feeling unwell any time the air conditioning came on. And it's 100 degrees outside. My wife and kid move to a hotel.
We get the air conditioning guy over to the house, and he looks at the AC coil and it's filled yucky gunk. Ok, clean that out and reinstall. Things seem good for three weeks.
Then our kiddo starts feeling unwell in the house again. AC coil is getting gunked up again, so we replace it. All's well for two days. Then kid starts feeling unwell again.
Let me just confess that at this point, I am no longer handling this as gracefully as the wise coach I present to the world. :}
Back to the hotel. This past week, got the air ducts cleaned and sanitized. Got mold air testing and indoor air quality testing done. Both tests come back clean.
But now, it's not just my kid, my wife and I are feeling unwell when we are in the house. We deep clean the carpets in case it's that. Nope no difference. Feeling worse in the house.
We are having a succession of mold and air quality experts over to try to figure it out. We've ruled out some stuff but have not identified the problem. Current theory is it's in the walls somewhere. Having people come out with moisture meters and infrared cameras. And to potentially drill holes in the wall and take a look.
Our family is now relocated to a local Residence Inn, in a little two bedroom suite. even the two cats. One of which is now hiding under a weird impossible to reach nook in the hotel room kitchen.
You would think by now, I'd be pulling my hair out and extraordinarily stressed out.
But at some point, I surrendered to the fact that this is happening. Not that I'm not doing everything I can fix the situation. But I've let go of emotional baggage of it all.
Yes the money is adding up and it's painful. But that's why we have an emergency fund. And this is a legit use of it.
Yes, I'm frustrated with the upheaval we enduring as a family - especially a family who has been through a hellish gauntlet with our kiddo's health for the past four years.
But, emotionally I'm doing fine. There's a value to a certain kind of surrender. Not the giving up kind of surrender.
But the letting go of the "this can't possibly be happening to me/us" thoughts has freed me up to just deal with shit and get on with it.
It's all a good analogy for the Founder Journey.
Surrendering is not giving up. Detachment doesn't mean not caring.
In this week's Rocket Ship Founder Podcast Episode, I talk about the value of surrender when navigating the inevitable challenges of Founder life.
I cover:
What it means to surrender without giving up
How to get yourself to a healthy (or healthy as possible) place during setbacks
How to get perspective in the midst of the grind
This 14-minute listen is offers some helpful wisdom for both business and life.

Ep. 52 How to Handle Negative Feedback
Hi {{contact.first_name}},
"When people tell you something's wrong, they're usually right. When they tell you how to fix it, they're usually wrong."
-- Bill Hader
One of the constants of Founder life is negative feedback. It's going to happen all along the way. And it will be inbound from any number of sources:
- Family and friends (even when well intentioned)
- Investors
- Prospects
- Customers
- Team members
- Co-Founders
- Yourself
As humans, we are wired to prioritize negative information over positive information. It's baked into our survival instincts.
In my experience, one of the traits of great Founders is the ability take in negative and catalyze it into positive action.
But it isn't always so easy. Our businesses are our babies, so it's very easy to take negative feedback personally.
Negative feedback is often fuel for action, via the "Just wait, I'll show them!" response.
But that path, while providing lots of fire, still hands a disproportionate amount of power to things outside of you.
The key is to be able to take in the feedback, stay grounded and centered, and move forward.
This week's Rocket Ship Founder Podcast Episode, all about taking in feedback in positive and healthy ways.
I cover:
The Larry David Story - how we are wired to dwell on the negative.
How negative feedback triggers deep stories about ourselves (and how to rise above them)
3 steps to staying centered and positive when receiving negative feedback.
This 15-minute listen is offers some helpful wisdom for both business and life.

Ep. 51 I don't know what I'm doing
Sometimes, we say the quiet part out loud.
Recently, I had a client express the Founder version of this perfectly. During a session, they paused and said,
The thing about this gig is, you can’t openly say “I don’t know what I’m doing."
You have to present with confidence to all of your stakeholders - team, customers and investors.
Even when you've never done this before. And the business isn't really figured out yet - market, product, team and business model are usually in flux.
I've been mapping out the different sets of skills Seed and Series A Founders need to come up to speed on.
There are 3 big buckets:
- Accelerating product-market fit and scalable sales
- Building a high performing org
- Growing yourself into a confident growth CEO
Founders usually have strengths in one of those buckets - and scramble madly to learn the rest.
But the list is long, and the runway is short. You need accelerators. That means taking advantage of:
- Coaches who have been through it
- Mentors who know the terrain
- Books, courses, communities
The challenge of course, is knowing which of these accelerators will actually serve you
In this week's Rocket Ship Founder Podcast Episode, I provide guidance on how to choose the right accelerators for your growth and development.
I cover:
Why its critical to locate yourself on the Find It, Nail It, Scale it map.
How to filter information from books, podcasts, etc so you can
How to pick the right coach for you
- Bill Hader's insightful advice for taking feedback
This 15-minute listen is a great one in learning to communicate and lead confidently, even in challenging circumstances.
To your success!
Steve
PS When you are ready, I have one open spot to work one-on-one with me. If you're a Founder navigating the Seed to Series A journey who wants to:
Accelerate PMF and scalable sales
Build a high performing team
Step into a new level of confidence as a leader
Email me at steve at steveaugustcoaching.com and we'll set up a time to connect.

Ep. 50 How to help your team keep the faith
"How do I keep up team morale and faith as we are trying to get to product market fit - especially when it's taking a lot longer than any of us expected?"
This week, I had no less than three Founder coaching sessions where we dealt with different takes on this question.
In each case, I asked the Founders, "how are you navigating this stretch?"
Answers were along the lines:
"we understand it's a process"
"we wish we were further along, but staying positive and breaking things down into steps"
"we'd like it to move faster but we also are learning the market"
"we're staying focused on what we need to do"
My response back was, "that sounds great, do you want your team to approach it the same way?"
Of course.
"How can you make it be THE WAY your company approaches these situations?"
You see, stretches like these are an opportunity to build the behaviors, values and culture you want your team to exhibit.
But it only happens if you coach and communicate those expectations to your team.
In this week's Rocket Ship Founder Podcast Episode, I cover:
Why its critical to work this at the behaviors/values/culture level
The 3 key things to communicate in these situations
How to avoid toxic positivity
The ONE phrase that will save you and your team a ton of stress in challenging situations
This is a good lesson in communicating and leading confidently, even in challenging circumstances.
PS I have two open spots to work one-on-one with me. If you're a Founder navigating the Seed to Series A journey who wants to:
accelerate PMF and scalable sales
build a high performing team
become a confident authentic leader
Reply back and we'll set up a time to connect.

Ep. 49 How to stop kicking yourself
This week several of my Founder clients were in "kicking myself mode."
"Kicking myself mode" happens when you've encounter a painful challenge. Then through trial, tribulation and some very hard decisions, figured it out and gotten past it.
The funny thing about "kicking myself mode" is that it usually kicks in after you've actually gotten to the other side of the challenge.
There's good reason for that, of course. In the midst of dealing with the challenge, you are too engrossed and consumed by the challenge itself.
This phenomenon isn't limited to business, it's part of regular life as well. The themes are classically:
1. Why didn't I know better?
2. Why didn't I act sooner?
3. Why didn't I trust myself more?
In the aftermath of a challenge, variations these three questions echo in our minds, consuming energy and ensuring that the challenge gets in a few more shots at us.
In this week's Rocket Ship Founder Podcast Episode, I talk about how to get out of "kicking yourself mode" and move forward with a positive and productive mindset.
Key takeaways:
- What to do with your emotions when they are so intense.
- What to hold on to and what to let go of in the aftermath of any challenge.
- How to move forward and not be dragged back down.
This 15-minute listen is definitely a great life lesson for any Founder.
PS I have two open spots to work one-on-one with me. If you're a Founder navigating the Seed to Series A journey who wants to:
- Accelerate PMF & scalable sales
- Build a high performing team
- Become a confident authentic leader
Send to steve@steveaugustcoaching.com to set up a time to connect.

Ep. 48: Do your work early
QUICK ASK: Before I leap into to this week's podcast episode intro, I have a favor to ask. If you have gotten value from my Rocket Ship Founder podcast, I would really appreciate it if you could give it a 5 star rating and post a review wherever you listen to it (Apple Podcasts, Spotify) Really appreciate it! Ok, let's get to this week's episode.
One thing you should know about me is that I'm a serious NBA fan. I was not built physically for the game of basketball, but I really love it.
There's a phrase in basketball: "do your work early."
What does this mean?
It means that the flashy dunk, the smooth turnaround, the defensive block that brings the crowd to their feet isn't really where the important action is.
They are just the end product of the work that was done earlier.
They don't happen unless the player has gotten to their preferred spot on the floor to initiate the action. Or defensively, if the player has prevented his opponent from getting to their preferred spot.
They don't happen unless the player has studied the tendencies and defensive sets of the other team.
They don't happen unless the player has prepared themselves physically to have the stamina to do it at the end of the game when it most counts.
This is the early work. It isn't flashy. It's often tedious and repetitive. It's done away from the spotlight.
But it's where success is actually born.
Mixing my sports up here, I think Muhammed Ali said it best:
“The fight is won or lost far away from witnesses – behind the lines, in the gym, and out there on the road, long before I dance under those lights.”
This is an important lesson for Founders.
In this week's Rocket Ship Founder podcast episode I talk about doing your work early. Key takeaways:
- What is the early work?
- How you are going to pick your hard, it's just about the timing.
- How the early work changes as you scale.
This 11-minute listen is one of the most important lessons of Founder life.

Ep. 47 Turning Roadblocks into Runways
Your business is trying to tell you something.
This week I was working with a Founder who has an amazing product but has been struggling with an extremely long sales cycle and underperforming sales people.
The pattern was they'd get a client on board for a proof of concept phase for their software. It would initially go very well but then the last five yards would stretch out forever to achieve the final pieces of integration. Their support folks would work wonders over a few months to get everything working.
They'd think that got everything worked out with their product and it would be smooth sailing from there.
But then the pattern would then repeat with the next client.
This brought back memories of my first startup. And the lesson I wished I'd learned faster.
A repeating pattern of a great product requiring a huge amount of people work to product the result the customer wants is a huge red flag on your business model.
Your business is trying to tell you, "You don't have a pure product business model. You have blended product-service business model."
While this sounds like a setback in a world focused on scalable SaaS, it's actually a huge opportunity, if you know how to play it.
In this week's Rocket Ship Founder podcast episode I talk about how to navigate the turbulence of Seed Stage. I cover:
- Identifying the Need for Change: Learn how to recognize the signs that your current model isn't serving your startup.
- Navigating the Pivot: We explore practical strategies to reframe and adjust your business model, including real-life examples of successful pivots.
- Seizing the Opportunity: Discover how to leverage the inherent opportunities that come with business model changes.
This 11-minute listen is one of the most important lessons I wished I'd learned sooner!

Ep. 46 The Wolf You Feed
Seed Stage is one of the toughest phases of your business journey. After the early wins of first customers and funding, things get really hard.
Your product isn't nearly as ready as you thought it was.
Your sales and marketing isn't punching through.
Team members who you thought were great turn out to be disastrous.
The market shifts and you have to adapt.
There are a dozen other disasters and crises that you never saw coming.
Any and all of these happen during Seed Stage.
And you are doing it all with a limited runway.
Maybe the toughest thing is that as you navigate all this, you may feel like you are not making progress. Your sales aren't happening the way you thought. Your product is full of bugs. Some part of your team feels like it's about to implode.
It's super stressful. It can cause you to question your abilities, your vision and whether you are really up for it.
So how do you stay positive and focused through all the mess?
It comes down to the wolf you feed.
There's an old parable:
An old grandfather was teaching his grandson about life:“A fight is going on inside me,” he said to the boy.“It is a terrible fight and it is between two wolves. One is evil–he is frear, anger, envy, sorrow, regret, greed, arrogance, self-pity, guilt, resentment, inferiority, lies, false pride, superiority, and ego.”He continued, “The other is good – he is abundance, joy, peace, love, hope, serenity, humility, kindness, empathy, generosity, truth, compassion, and faith. The same fight is going on inside you–and inside every other person, too.”The grandson thought about it for a minute and then asked his grandfather: “Which wolf will win?”The grandfather simply replied, “The one you feed.”
In this week's Rocket Ship Founder podcast episode I talk about how to navigate the turbulence of Seed Stage. I cover:
- Understanding the Seed Stage wolves
- One killer exercise for feeding the right wolf
- 2 habits to keep you positive and resilient
This 12-minute listen is one of the most important lessons I've learned in Founder life.
To your success!
Steve
PS I coach an amazing group of Seed Stage founders. If you'd like to join our tribe, reply back and we'll set up at time to talk.

Ep. 45 The Power of Finding Your Tribe
Last week was my birthday. I gave myself what turned out to be one of the greatest gifts I've ever received - a four-day retreat in Southern California.
What made it such a great gift?
It wasn't the location, though it was very nice.
It wasn't the food, though there was plenty of good food to be had.
It wasn't the amenities and activities, though I got some great yoga and a cold water immersion.
It was the people I was with. You see, this retreat was specifically for men who are caring for kids with rare diseases (or caring for themselves having a rare disease).
Some of you may know that our 21-year old has been suffering from a Spinal Cerebral Spinal Fluid Leak over the past four years. This is an extremely painful and challenging condition. The headaches are intense. There's severe sound and light sensitivity. There's brain fog. And as the condition progressed, our kid suffered from non-epileptic seizures.
I am happy to say that earlier this year they had a procedure that fixed the leak and the leak symptoms have abated. But there's lots of therapy and reconditioning to work through to get them to a good place after four years of suffering.
The intensity of the challenge for our family and for me was unlike anything I've ever experienced. It is so far outside the norm, that most people can't quite imagine it.
So what made the retreat I attended such an amazing gift, was that I was with six other men who knew exactly what it was like to be in this kind of situation. We were able to share openly about our experiences, our grief, where we felt like we showed up, and where we felt like we fell short.
It was one of the most powerful experiences I've had in my entire life.
I went into the retreat feeling like I've been in a deep trough. I was honestly pretty spent.
I came out of it feeling renewed and like I had not just regained my own strength, but could draw on the collective strength of my guys.
For the first time in my life, I really felt the power of finding your tribe.
While the stakes aren't quite as high, being a startup Founder is definitely outside the norm of most people's experiences - and definitely super challenging.
There's not many situations where you can talk about what's truly going on with you. The temptation is to isolate and soldier on. But eventually that will grind you down.
In this week's Rocket Ship Founder podcast episode I talk about the power of finding your tribe. I cover:
- The ease and danger of isolation as a Founder
- Why it's so important to have a Founder tribe
- How to find your Founder tribe
This 12-minute listen is one of the most important lessons I've learned in Founder life.
PS I coach an amazing group of Seed Stage founders. If you'd like to join our tribe, write me at steve@steveaugustcoaching.com and we'll set up at time to talk.

Ep. 44 Sharpening Your Saw
This Sunday is my birthday and I've given myself a great present. As you read this, I am at a retreat in Southern California to step back and recharge. I'm not taking my computer. I'm going to be offline as much as humanly possible. I'm going to do a lot of nothing.
This is actually a hard thing for me to do. But time has shown, it's one of the biggest enablers of progress.
As Founders, our inclination is to drive ever harder. To keep grinding to the next milestone.
I'd like underscore the importance of taking some time off. This principle is often illustrated through the metaphor of "sharpening the saw."The analogy refers to an old parable where a woodcutter, driven by the need to cut more wood, works incessantly without ever stopping to sharpen his saw. Consequently, as the saw dulls, his productivity decreases. Eventually the saw breaks and he gets injured.
If he had paused to sharpen his saw, he would have maintained his productivity and even increased it in the long run.Much like the saw, our minds and bodies are tools we use to create, innovate, and lead. However, the rigors of leading a startup can often lead to burnout, decreased productivity, and impaired decision-making, akin to the woodcutter's dull saw. This is why it's crucial to take time to "sharpen the saw," or in other words, to rest, rejuvenate, and recharge.
This week's Rocket Ship Founder podcast episode is dedicated to sharpening your saw. I talk about:
- The 3 key benefits of stepping away
- 2 critical steps to set yourself up to sharpen your saw
- Breaking through the stigma of time off
This 13-minute listen is one of the most important lessons I've learned in Founder life.
To your success!
Steve

Ep. 43 Superpowers & Kryptonite: The Neurodiverse Founder Journey
Recently, I was diagnosed with adult ADHD. Looking back over my entrepreneurial career with this Neurodiverse lens, I see my strengths and my challenges in a new light.
It turns out that Founders tend to have a greater Neurodiversity, whether ADHD, dyslexia, being on the autism spectrum. In one estimate, people with ADHD were estimated to be 500% more likely to start a business.
In the business press, some have painted neurodiverse conditions as a superpower, especially in the context of famously successful Founders like Elon Musk, Steve Jobs and Peter Thiel.
However, like all things in life in business, our greatest strengths also create our greatest challenges.
In this personal and thought provoking episode, I talk about:
- Some striking stats about Founders and Neurodiversity
- My Founder journey and grappling with ADHD
- Neurodiversity: something to harness or to manage?
- 3 strategies to maximize neurodiverse strengths and mitigate challenges
This 14-minute listen is an important listen for Neurodiverse Founders and the people who work with them.
PS Cohort 3 of 2X Accelerator: Essentials of Easier Sales starts June 12th. I'm looking for B2B Founders who want to make their sales 2x easier in the next 45 days. Details here!

Ep. 42 Seed Stage Pitfalls & VC Life w/ Natalie Ledbetter
This week's Rocket Ship Founder podcast episode features my first ever interview episode - and I think it's a great one to start with!
I speak with Natalie Ledbetter, People Ops Exec, Startup Advisor, TedX Speaker and Former Operating Partner & Head of People at Boldstart in NYC.
In our wide ranging conversation, we discuss:
- Natalie's fascinating international personal journey to and through the startup world
- The most common pitfalls for startup Founders
- What you'd be surprised to know about how VC's operate
- Her philosophy on how to nail People Ops
We also talk about The Seed Stage MBA 3-Day bootcamp we are partnering on. It's coming June 13-15th! Get the essential skills knowledge to avoid costly pitfalls, extend your runway, and accelerate to Series A or a sustainable business.
This 40-minute listen is chock full of knowledge and wisdom for Founders.
To your success,
Steve

Ep. 41 Are you really the best person for this?
I'm not sure I'm the best person for this job.
I've heard this sentiment in a bunch of conversations I had with Founders over the past two weeks. So let's go right at this.
Leading a startup is hard. Seed Stage is especially hard because it's the stage where you have to go from being an awesome "something" - designer, product person, developer, visionary - to being a true business leader.
You are learning so much about the all of the jobs in the business: the stuff you know how to do plus all the stuff you don't know. How to hire, how to get people aligned, how to drive product-market fit, go to market strategies and tactics, how to manage a board, and a bunch of other stuff you never knew you were going to need to learn.
So it's only natural when things are challenging to sometimes ask yourself, "Am I the best person for this?"
The answer is: At Seed Stage, there's no one better for this than you.
In this week's Rocket Ship Founder episode, I break down:
- Why you are not only the best person, but the only person for this job at Seed Stage
- What to do when you start comparing yourself to other Fouronders
- How to show up with confidence, even when you don't know why you are doing
Steve
*PS Want to get the confidence to know you are the right person for the job? The Seed Stage MBA 3-Day bootcamp is coming June 13-15th! Get the essential skills knowledge to avoid costly pitfalls, extend your runway, and accelerate to Series A. Limited to 5 founders and their teams.

Ep. 40 The 3 Critical Things to Go from Seed to Series A
On the surface, getting from Seed Stage to your Series A should be a pretty straightforward proposition. You basically need to demonstrate three things: Great traction, a high performing team and leadership that everyone can be confident in.
Well, that sounds pretty straight forward, right? But as we know, life isn't so simple. The Seed Stage is often anything but smooth. It's a nine to 24 month journey of endurance and resilience.
Traction is slower than your early wins suggested they would be.
Some part of your team is not performing the way you hoped.
And as a Founder you and your founding team find yourself routinely overwhelmed putting out fire after fire, while learning how to lead a growing organization, which likely you've never actually done before. It's a lot.
And the thing is, there's not a lot of training for this phase. There's plenty of accelerators and support systems for the pre-seed/idea stage. And there's a lot of stuff for established companies that need to grow.
But there's not much support for Seed Stage Founders, when almost everything is being figured out - all while the clock is ticking to get to a Series A or a sustainable business.*
In this week's Rocket Ship Founder episode, I break down:
- The 3 things you need to do to navigate Seed Stage journey
- Why Seed Stage is especially challenging (and how to attack it)
- The single biggest shift you can make to out of overwhelm and into confidence (even when things are crazy)
This 14-minute listen is the advice I wish someone had given me as a Seed Stage Founder.
*PS The Seed Stage MBA 3-Day bootcamp is coming June 13-15th! Get the essential skills knowledge to avoid costly pitfalls, extend your runway, and accelerate to Series A. Limited to 5 founders and their teams.

Ep 39. How to save $150k of runway
Getting your Seed funding is a huge win. But as soon as your funds hit your account, you and your team on the clock.
You have only so much runway to either get to demonstrate the traction you need for your Series A or a sustainable business run rate.
Every month of runway in Seed Stage is precious. Even more so in the current environment where money is tighter and VC's are being MUCH more selective with funding and valuations.
Business is always challenging. But for a Seed Stage Founding team, the need to extend runway has never been greater.
What really hurts is avoidable mistakes that dent your runway and blunt your momentum.
A single mis-hire can easily cost $150k in shortened runway and lost momentum. Ouch.
As a Founder, I made a lot of costly mistakes. As a Founder coach, I see a lot of Seed Stage Founding teams make similar mistakes.
Sometimes in life and business, our best chance of success is just about avoiding as many of the most avoidable mistakes as we can. (While giving ourselves grace knowing that mistakes are inevitable when doing something new).
In this week's Rocket Ship Founder episode, I talk about how to save at least $150k of runway simply by avoiding common Seed Stage pitfalls. I cover:
- Framing Seed Seed Stage in a way that will help you make better decisions
- The #1 biggest way to save $150k of runway
- What you definitely should not spend on during Seed Stage
This 14-minute listen is the advice I wish someone had given me as a Seed Stage Founder.
To your success,Steve
PS COMING SOOON: The Seed Stage MBA program. The only program of Essential Skills and Coaching specifically for Seed Stage Founding Teams.

Ep 38. What I learned from 26 Seed Stage Founders
Last week I had the absolute privilege to facilitate 26 Seed Stage Founders at a 3-day retreat in Portugal.
The Founders at this retreat are whip smart, ambitious and working on huge game changing ideas in biotech, food tech, robotics, crypto/Web 3.0 B2B software as well as consumer goods.
It was a brilliant few days of sharing, learning and camaraderie in the Founder journey.
My job was to teach my most valuable lessons, and give participants as many opportunities to learn from each other as I could create.
As the facilitator and the person presenting content, I shared the most important key lessons and skills from my Founder journey and life. And I think everything landed well.
But the little secret of these events is that the facilitator learns as much or more from the participants. And this was no exception.
In this week's Rocket Ship Founder episode, I talk about the biggest lessons I learned from leading, coaching and talking with 26 Seed Stage Founders. Things I'll cover:
- The 3 universal issues that every Founder faces no matter what category
- The 2 biggest issues Founders navigate in Seed Stage
- The single most disorienting thing once you get to your Series A
- And a bonus - one phrase that can help save your relationship with your significant other
This 13-minute listen will give you a real sense of perspective on your Founder journey.
PS I have one open spot to for a Seed Stage Founder to work with me one-on-one. If you're a Seed Stage Founder facing challenges on your progress towards your Series A, let's talk.

Ep. 37 ADHD and Reducing Gravity
This past week marked an interesting event for me. After 54 years of living, I got officially diagnosed with ADHD. It's clicked together some long standing puzzle pieces for me.
It helps explain why...
...writing an email that should take 2 minutes takes me 10 minutes
...even though I do get stuff done, it always feels like I'm grinding vs being in flow
...once I solve the hardest problems of a challenge, I lose interest in the easy finishing stuff
...I have a habit of cutting across another person sentence before they've finished it
...it takes me forever to start something that requires deep thinking
I suspect this has been a constant in my life. But I grew up in the 70's and 80's so it wasn't really diagnosed so much back then. And when I was younger, I had the youthful energy and drive to push through it.
As I've gotten older, I've found it's harder and harder for me to focus on anything for nearly any length of time. It goes beyond the typical resistance and procrastination.
The net result has been I have to work far more hours than I need to.
I've found hacks over the years. For example, having to prepare for a specific event definitely gets me moving and through the resistance.
But the reality is ADHD has been a huge net drag on my ability to achieve the things I'd like to in my business and life.
While I have all the other challenges of business building, they are ALL impacted by this root problem of ADHD.
It's been there the entire time, hiding in plain site.
This is my first week on Adderall, and I'm noticing a different. I'm able to jump in to deep thinking projects easier. I'm more able to stay on task and get into flow. Stuff is a little easier.
This is as great parable for our businesses. Sometimes there's a root problem that we've become so acclimated to, we don't even see it. But it's making everything we do harder.
But if we address it, everything gets easier.
Here's the analogy. Imagine you have a rocket. To get it to go higher, you can build a bigger engine. You will go higher, but you'll have to carry and burn more fuel (which means your engine needs to be bigger).
But you can also think about ways reduce gravity. If you can go faster than if you just built a bigger engine. (And when you do build the bigger engine, you will get more out of it).
In this week's Rocket Ship Founder episode, I cover:
- 3 ways to recognize a root problem hiding in plain site
- What to do once you find it (ie. reducing gravity)
- How to make sure you nip these problems in the bud in the future
This 16-minute listen is will get you thinking about your business from important different angles.
PS I have one open spot to for a Seed Stage Founder to work with me one-on-one. If you're a Seed Stage Founder needing to accelerate your progress towards your Series A, let's talk.

Ep. 36 SVB and WFIO Moments
While things seemed to be resolving, the past week have been incredibly stressful for any Founders who had their funds with SVB.
Several of my clients and Founder Friends have been caught up in what is known is a WFIO moment. If you're not familiar with the term WFIO, it's one Ben Horowitz of Andreessen Horowitz uses.
WFIO stands for, "We're Fucked It's Over."
Having run my startup during the 2008 financial crisis (in fact we launched the week the first week of October 2008), having a banking crisis is one of the most WFIO type of moments.
The challenges of a Seed Startup are supposed to be finding product market fit, building your team, and learning how to operate a business that hasn't figured out most of what makes a business successful.
Having your bank go under with your funds is generally not on the startup Founders Bingo card.
Fortunately, the FDIC stepped in and saved the game, but that was a close call. And a lot of Founders spent the week stressing out over whether they had funds to make their next payroll vs pushing their business forward.
So what can we do in these extreme circumstances? This week I talk about:
- When staring at a huge problem (i.e. all of our cash is out of reach), how to break it down into the smaller problems and sequence them.
- How to get clarity by separating what's objectively true from fear and projection
- Finding hidden blessings and opportunities even (sometimes especially) in the darkest crisis
Every time I hit a crisis in my business, it forced to me to get real about what was performing and essential, and what was not performing and a luxury.
Founders and companies that weather this storm will come through stronger.
This 11-minute listen is chock full of hard-earned wisdom and will serve you well through big or small times of crisis.
To your success,
Steve
STEVEAUGUSTCOACHING
Helping Founders Build Rocket Ships
PS I have one open spot to for a Seed Stage Founder to work with me one-on-one. If you're a Seed Stage Founder needing to accelerate your progress towards your Series A, let's talk.

Ep. 35 One Simple Thing To Improve Your Hiring
Every Founder I've ever known has hit this same scenario:
1. Have a new hire they need to make
2. Push out job description to network and hiring sites
3. Get a decent amount of resumes
4. Pare down resumes to identify candidates to interivews
5. Conduct many rounds of interviews
6. A candidate crushes the interviews
7. Candidate is hired, yay!
8. Things start off OK, but then quickly go downhill
9. Wonder what happened to the candidate who interviewed so well
10. Part ways and start over
While no one bats .1000 when it comes to hiring, this scenario is way too common.
So what do you do to prevent this scenario from repeating?
There's one simple thing you can do to dramatically up your odds. It's all about auditioning vs interviewing.
In this week's episode I talk about:
- Why this happens - and what to do about it
- The two things you are really hiring for - and why we often focus on the wrong one
- Auditioning for behaviors vs interviewing for skills
- Real world examples
This 10-minute listen will uplevel your hiring game!
To your success,
Steve
PS I have one open spot to for a Seed Stage Founder to work with me one-on-one. If you're a Seed Stage Founder needing to accelerate your progress towards your Series A, let's talk.

Ep. 34 Three things I wished I'd known about leading humans
This month, The Rocket Ship Founder podcast is all about building and leading your team.
One of the most important skills Founders need to learn is how to build and effectively lead their teams. Ironically, this is the area people get the least training on.
In the early days of your business when it's just a few close-knit people, things are pretty straightforward. I call it the "think out loud stage." People can just sort of think out loud and everyone it's pretty easy to have people aligned.
But when you get your first real money, and your team starts to grow beyond the original founding group, leading complex and diverse humans gets exponentially harder.
In this week's episode, I go over the three things I wish I'd known as a first-time Founder about building teams and leading humans, especially in Seed Stage.
I talk about:
- How knowing your Founder Type is critical for understanding your strengths and challenges in leading people
- The 4 levels of team skills and how to identify them
- How to hire for a role you don't have any experience with
PS I have one open spot to for a Seed Stage Founder to work with me one-on-one. If you're a Seed Stage Founder needing to accelerate your progress towards your Series A, let's talk.

Ep. 33 Finding your sweet spot leading your team
When it comes to leading a team, there's a dilemma I see for every Seed Stage Founder I've worked with. (And one I certainly experienced myself!)
Here's the scenario:
1. A Founder gives a team member an initiative to work on.
2. The Founder sits back and trusts team member to complete the initiative exactly they way expect
3. Team member completes initiative and presents the work
4. Work is not what the Founder expected, and doesn't measure up to what they had in mind
5. Founder starts doubting team member, next initiative Founder micromanages
6. Founder gets result they want, but now are in the weeds and team member is disempowered
The dilemma for a Founder is, "do I sit back and trust my team and hope things turn out the way, or do I micromanage and get what I want, but end up having to be in everything?"
Every Founder I've worked with has experienced this at some point.
How do you solve this dilemma? How to you find a sweet spot between trusting and not getting what you want and micromanaging.
This week's episode breaks down how to solve this dilemma and find your sweet spot as a manager and leader.
This is the episode I wish I had been able to hear when I was building my first team. It has lessons I wish I had known, specifically...
- The 3 critical keys to building and leading growing a great team
- The most important thing people don't realize about hiring the right people
- How to ACTUALLY create a culture of accountability
This may be the best 12 minutes you spend this week.
PS I'm looking for on Seed Stage Founder to work with personally starting March 1st. If you're a Seed Stage Founder with a product and a growing team, let's talk.

Ep. 32 3 Essential Things to Know About Managing Your Board
This week's episode comes in response to a question I got from one of my subscribers. I love getting questions from Founders, so if you have any, reply back and with yours and I'll respond in an upcoming episode.
This subscriber wanted to the lowdown on Boards. As a seed stage founder, you know that building and managing a board of directors is a critical step in the growth of your business. But, if you're new to the game, it can be a daunting to navigate.
I remember when I was leading my first startup, I had NO prior experience with reporting to a board. With our first funding round, suddenly I had to work with and answer to my board.
There were a lot of things that had I known, it would have made everything less stressful and maximized the value of my board members.
I wish I had known...
- The #1 thing to keep in mind when working with a board
- The one thing NEVER to do with your board
- How to get the most out of every board meeting
I answer all this and more in this week's episode. Check it out!
PS I'm looking for on Seed Stage Founder to work with personally. If you're a Seed Stage Founder with a product and a growing team, I can help. Set up a simplicity session here.

Ep 31: Surthriving Seed Stage
After a two week hiatus, I am back with another Rocket Ship Founder Podcast Episode. My hiatus was due to taking my 21-year old to LA for treatment for a recurring debilitating condition.
During the trip down to LA from our home in Portland, the days leading up to the procedure, and the procedure itself, the universe threw us a bunch of curveballs.
Our train was canceled
There was a med van ride from hell
There was an actual 4.2 earthquake,
A broken MRI machine
And a scary twist in the procedure itself
We are home now safe and sound and our kiddo is recovering. I'm getting back in the swing coaching my Founder clients.
But I keep thinking about that trip. It felt we would swing from surviving to thriving from day-to-day. Even moment-to-moment.
We got thrown really big challenges and threw all our ingenuity and resources at it. And got through it.
And while the stakes are very different, it reminded me of my Seed Stage Founder journey - and what my clients experience as well.
The challenges sometimes come fast and furious. One minute you are thriving with a big win. The next you are surviving a sudden a existential challenge.
And then back again.
It comes so fast you might as well smash "survive" and "thrive" together. You are "Surthriving."
In this week's episode I share:
- Update on my recent Odyssey to LA and back
- Why "Surthrival" is the perfect way to describe the Seed Stage journey
- Three keys to Surthriving
PS If you are a Founder who is is ready for a new level of support "surthriving" Seed Stage, let's talk. I've got space for one more client. Set up a time here.

Ep. 30 We are most powerful where we are most vulnerable
I had an entirely different topic slated for this week's Rocket Ship Founder Podcast Episode, but felt moved to dig into something deeper: the dichotomy of vulnerability and power.
Part of the ironic nature of the Founder's journey is that we are constantly called to outwardly project confidence and strength - all the while knowing/feeling all of the weaknesses and shortcomings in ourselves and in our business.
The common thinking is that vulnerability is weakness. And in geo-political matters, that's probably true, given the arc of human history.
But in the "Bigger Game" of our own personal development, I've come to believe that where we feel most vulnerable is where we are most powerful.
Because I see this funny thing happen when we surrender to a challenging moment: we let go of what we thought we should be and accept into what actually is and who we truly are.
And I am convinced there is nothing more powerful than true and total self acceptance.
Fair warning: this episode will be especially personal and vulnerable.
In this week's Rocket Ship Founder Podcast Episode, I share:
- What's been going on with me in my business and life, and why I'll be on a train to LA next week
- My experience with therapeutic psilocybin
- How I broke down and came out the other side
- Two powerful techniques to navigate big challenges and rollercoaster emotions
If you are a Founder who needs support in becoming the CEO your business needs, reach out to me at steve@steveaugustcoaching.com and we'll do a Simplicity Session.

Ep. 29 What's between you and your next breakthrough
In this week's Rocket Ship Founder Podcast Episode, I talk about why facing the biggest uncomfortable things in your business is one of the essential skills Founders need to cultivate.
Because if you don't face the big uncomfortable things in your business, you'll still end up dealing with their effects on your business every day. And eventually it catches up to you anyway.
The good news is that your next breakthrough is on the other side of the uncomfortable stuff.
In this week's Rocket Ship Founder Podcast episode, I cover:
- Why facing the uncomfortable creates breakthroughs
- The single most important question to ask yourself and your team
- How to make friends with the uncomfortable.
- The question that helps you move forward when things are challenging

Ep. 28 The Pattern That's Killing Your Business
Welcome to 2023! Ready to get back in the groove? This year, I start by renaming my Podcast - and tackling a hugely problematic pattern that can eventually kill your business.
First the name change.
After tackling saying the mouthful of Rocket Ship Business Academy for 27 Episodes, I've changed the title the much simpler and on point Rocket Ship Founder. Less is more. Simpler is better. Onwards!
Now about the problematic pattern that can eventually kill your business. It will also burn you out if you let it persist.
It's one I experienced with my first startup, and a pattern I been helping a number of clients to break out of.
I call this pattern the "tent pole" pattern. It goes like this:
1. Good to great month/quarter/year of sales
2. Tepid to awful month/quarter/year of sales
3. Frantic effort to revive sales
Repeat until exhaustion, burn out, end of runway. Not a fun place. To be.
In this week's Rocket Ship Founder Podcast episode, I cover:
- Why the tent pole pattern happens
- How it will eventually kill your business - and burn you out
- How to get break out of the pattern and consistently accelerate growth
PS Here's how to work with me in 2023:
2X Accelerator - Double your product-market fit and scalable sales velocity in six weeks. Next cohort starts February 13, 2023! If this episode resonated with you, set up a time for a clarity session pronto! (link below)
Founders Mastermind - my group program to help Visionary B2B Founders accelerate their transformation into growth CEO's.
Private Coaching - I have two new spots open to work with me one-on-one. For Founders with at least $2M in revenue or funding.

Ep. 27 How to Crush 2023
Wow, hard to believe we are at the end of 2022! All this week, I've been working with my clients to take stock of progress in 2022 and set up to crush the first six weeks of 2023.
In this week's Rocket Ship Business Academy Podcast episode, I share the sequence of exercises I take my Founder clients through to set them up to come out of the gate roaring in the new year.
I cover how to:
- Recognize the progress you've made in 2022
- Frame your 2023 goals
- Identify the most important problem to solve
- Build out your first six weeks of the year
And as a special holiday gift, I am sharing the exact Notion template with the exercises I use with my private clients to jump start 2023!
The template is free and can be duplicated into your Notion account. Don't have Notion account? No worries, it's free to sign up!
To get it, just send me an email at steve@steveaugustcoaching.com with the subject "Jumpstart 2023!"

Ep. 26 When The Hits Keep Coming
This week's Rocket Ship Business Academy Podcast episode is one of my most personal. I hope you will find valuable to you as a Founder, but even more importantly, as a person.
This week was a challenging week for several of my Founders. There was dev team drama, co-founder dysfunction, product milestones slipping, big clients wins falling through at the 11th hour, dealing with crazy board members and the usual day-to-day fires.
For me, it was a challenging week as well. Our now 20-year old kiddo has been fighting a debilitating and painful medical condition called a CSF Leak over the past three years. In April this year, we finally found a doctor who could patch them. We've had a good seven month run and life was slowly getting back to something resembling normal. Until last Sunday, when their patch failed and the leak symptoms returned.
In business and in life, it can sometimes feel like the hits just keep coming. You think you've got everything buttoned down and under control. And then you get kicked in the teeth.
Yet, here we are. Still in the fight. Pushing for the things and people we care deeply about.
In this week's Rocket Ship Business Academy podcast episode, I share 3 hugely important things I draw on when I hit these waves of challenges. I'll cover:
- The single most important question to ask yourself when you are facing tough challenges
- Why you need to focus on the pain, and what you need to let go of
- How to find the hidden blessings in every crisis
If you are facing a tough challenge, I hope this episode gives you some comfort and some tools to help you through.
Got questions on leading your business? Email me at steve@steveaugustcoaching.com and I'll answer it on an upcoming podcast episode!

Ep. 25 Ruthless Simplicity (Your Real Job)
When I was running my startup I loved solving complex problems and creating elegant solutions. As a Type V - Visionary Evangelist Founder Type. And I had a good talent for it.
But like a lot of things that helped me in the early stages of my business, my love of creating elegant solutions for complex problems ended up working against us.
How could that be?
Here’s how. One of the biggest killers of growth is complexity. When you start out with your business, things are naturally simple. You have one product. You have a co-founder or a small team. You (hopefully) have a pretty clear handle on the pain you solve for people.
But as the company grows, complexity starts creeping in. Different customer types, different product decisions, staffing decisions, sales channels, pricing models, etc.
One of the hardest lessons I learned about being a Founder/CEO is that your real job is to create Ruthless Simplicity
- Why I call it Ruthless Simplicity
- How you know you need it, and what it gives you
- 3 steps to creating Ruthless Simplicity
If you are struggling with stubborn challenges, this episode will give you a powerful lens to see your way through.
Got questions on leading your business? Email me at steve@steveaugustcoaching.com and I'll answer it on an upcoming podcast episode!

Ep. 24 You're Playing A Bigger Game (Even if you don't realize it)
For the past few months, I’ve been almost exclusively focused on accelerating product market fit and sales. That’s because when it comes to accelerating your business, there’s nothing bigger than accelerating product-market fit and scaling sales.
But this week, I’d like to shift gears and talk about something that for Founders, is even bigger than sales, bigger than building and growing your team and bigger than mastering operational brilliance. It’s bigger than building a rocket ship business.
It’s the game of you. I call it the bigger game, because it’s the biggest game of all. And your playing it whether you realize or not.
You may think that once you achieve your desired goal, that you will be different. That the things about yourself will change.
But the reality is that the baggage you brought with at the beginning of this journey will still be there at the end, no matter what outcome - unless you unpack it and deal with it along the way.
As a Founder you will face all kinds of stresses. Uncertainty with everything. You will be triggered and your buttons pushed.
In this episode, I talk about playing the Bigger Game and give you two powerful questions that will give you the power to change how you experience everything in life.

Ep. 23 The Problem With Thought Leadership
I’ve had a few conversations with First-Time founders over the past week that have gone like this:
“So, what’s your strategy for build your pipeline and sales?”
“Mainly thought leadership and content marketing. “
You may ask yourself, “wait, what could possibly be wrong about thought leadership as a sales strategy?”
Well, that’s the thing. Thought leadership isn’t actually strategy.
It can be an important ingredient or an element of your customer flywheel.
But it’s not a sales strategy on its own.
In this week’s episode of the Rocket Ship Business Academy Podcast, I cover:
- What thought leadership gets you…
- …and what it doesn’t.
- Customer flywheels and what you need to build them
- The absolutely critical step to maximize the impact of your thought leadership
Need to accelerate your B2B sales and scalable product market fit? Reach out at steve@steveaugustcoaching.com

Ep. 22 Find It, Nail It, Scale It
I see a pattern over and over again with both my businesses and the Founders I work with.
There’s three times we kinda get kicked in the teeth.
The first is when we just launch and test our vision with the market.
The second is when we get initial traction and think we’ve cracked it.
The third is when we’ve cracked it and then we’ve got to scale it.
I think of these phases as: Find it, Nail it, Scale it.
In this week’s Rocket Ship Business Academy Podcast, I talk through the gotchas of each of these phases - and what to do to break through.
PS If you need to break through these urgently, the first 2x Accelerator for scalable market fit and sales is kicking off on October 31. The outcome is simple: To increase your product-market fit and sales velocity by 2x in six weeks. Write me at steve@steveaugustcoaching.com with the word “2x” to learn more.

Ep. 21 3 Things Keeping You From Growing Sales
If I could only solve one single challenge for Founders, what would it be?
Answer: Accelerate scalable product-market fit and sales.
Because if you figure out this challenge, you have the fuel to figure out all the other challenges.
But it’s a big challenge for any B2B business. And there are so many variables and angles on it that it can be overwhelming for First-Time Founders to figure out how to crack it.
So broke it down into 3 key things that keep you from product-market fit and scaling sales.
- Too much Sales Friction
- Not Enough Customer Conversations
- Everything At Once Overwhelm
In this week’s episode of the Rocket Ship Business Academy Podcast, I walk through these 3 blocks and what you need to do to clear them.
Steve
PS If you need to break through these urgently, the first 2x Accelerator for scalable market fit and sales is kicking off on October 31. The outcome is simple: To increase your product-market fit and sales velocity by 2x in six weeks. Write me at steve@steveaugustcoaching.com with the word “2x” to learn more.

Ep. 20 2x Acceleration
As Founders, we dream of building a rocket ship business that takes off, makes a huge impact and creates tremendous financial abundance.
It’s a wonderful dream.
The reality, of course, is it’s really hard to do.
We can’t flip a magic switch and suddenly have our business 10x.
But what if we can find places in our business where we can accelerate 2x?
Because before there’s a sale, there’s an offer, a prospect, a pitch, a proposal and a close.
What if you could systematically identify and create 2x acceleration opportunities in your business. How much knows how much you could increase your business’s velocity?
2x Acceleration is the topic of this week’s episode of the Rocket Ship Business Academy Podcast
Topics I cover:
- What 2x Acceleration means at different stages
- Where to look for 2x opportunities
- What happens if you accelerate the wrong things (at the wrong time)
2x Accelerator is also the name of a new program I am piloting in November. I’m really excited by the potential for this program to create wins and build momentum for your business. It’s specifically targeted for B2B Founders with a product in market who want to rapidly create product-market fit and sales breakthroughs.
Hit me up at steve@steveaugustcoaching.com and I’ll give you the details.

Ep. 19 You Have ONE Job
Founders who work with me know hear something over and over. They hear it so much, they probably get annoyed with me.
But it’s the essence of my work. And it’s critical to their success.
Here’s how it goes. Client or prospect comes with a laundry list of updates and challenges.
Then I dig in with questions and together we figure out “THE problem to solve.”
Because usually there’s one underlying problem to solve - and everything else is just a symptom of that problem.
You have ONE job: identify and solve that problem.
I talk about:
1. How to find THE Problem to solve
2. How to differentiate between THE Problem and symptoms
3. The core problems to solve at each phase of your business...
4. ...the key question to ask that will help you start solving them
Have a question you want covered on the podcast? Reach out to me at steve@steveaugustcoaching.com

Ep. 18 Sell Your Way To Product-Market Fit
This month is all about troubleshooting sales, the most common pressing challenge selected by the 2000+ founders who have taken my Founder Type Quiz.
One of the biggest challenges for any Founder or business is Product-Market fit. Often product-market fit is seen as a distinct challenge than sales. But in my experience, looking at product-market fit as a specific type of sales challenge is really helpful.
In this episode, I talk through:
1. Breaking down sales into three core components: traffic, conversion and economics.
2. What sales looks like at 0-1, 1-100, 100-1000 stages of your business
3. Which component to focus on in product-market fit
4. How your Founder Type impacts how you sell
5. Key gotchas with early stage sales
6. What absolutely not to do when working product-market fit
And remember: you can’t scale the hard sale!
Have a question you want covered on the podcast? Reach out to me at steve@steveaugustcoaching.com

Ep. 17 Fixing Your Web Site Won't Fix Your Sales (and what will)
This month is all about troubleshooting sales, the most common pressing challenge selected by the 2000+ founders who have taken my Founder Type Quiz.
Today I was talking with one of my clients and he mentioned that they decided not to renew their social media agency, since they weren’t getting any ROI (something that’s all too common). He was going to turn his attention to their website and update it.
I told him that’s fine, but it won’t fix your sales.
It’s not that they don’t need a web site.
It’s not that social media can’t be an effective channel.
In fact it’s not any one thing - web site, social, ads, etc - that will crack the sales challenge and give you the fast growth you are looking for.
But here’s what will.
There are 3 things that need to be in place:
- An offer that reliably converts for your ideal customers
- A way to consistently bring those ideal customers to you
- And a cost of acquisition and delivery that makes it all worth it
Another way to think of it is what Perry Marshall calls the Tactical Triangle: Traffic-Conversion-Economics
Of course this sounds simple in theory, but is much more challenging in practice.
In this week’s Rocket Ship Business Academy Podcast episode, I talk about how to put these in place and what’s required to make it happen:
Key topics I’ll hit:
- The very first step you need to take to make sales go
- The difference between your offer and your product/service
- How to create a compelling customer journey
Are you a Founder who feels alone in your journey? I've been there! Reach out to steve@steveaugustcoaching.com

Ep 16. How To Make Complex Sales Simple
This month is all about troubleshooting sales, the most common pressing challenge selected by the 2000+ founders who have taken my Founder Type Quiz. Recently, when I asked the question, when it comes to sales, what’s your single biggest challenge, one subscribers responded:
“Our sales is complex AND is highly affected by timing.”
I have personal experience with this as my first startup, the market research software company Revelation had a complex sale that was very highly affected by timing. This made it extremely hard to scale the business!
I can’t tell you all the frustrating ways I tried to solve that issue. I tried different marketing systems, different sales methodologies, different team members. I looked for a lot of silver bullets (spoiler alert: there are no silver bullets!).
I have to confess I never truly cracked it - until my company achieved its exit and I saw how the people who bought us operated.
It was all about making the complex sale simple. In this week’s Rocket Ship Business Academy Podcast episode, I talk about how to think through your complex sale and make it simple and less dependent on timing.
Key topics I’ll hit:
- How to simplify a complex sale
- How your Founder Type works against you (and what to do about it!)
- How to craft a selling proposition that breaks through the clutter
- How to identify ways to reduce timing dependencies

Ep 15. Growing Sales: The 4 Founder Blindspots
As typical of many Founders, I was always looking for the silver bullet: that one thing that would enable us to bust through and get that rocket ship momentum.
We need a killer new product or feature, I’d think.
Or we'll get on Hubspot and when the content happens it’s all gonna take off.
Or now that we’ve spent a fortunate on Salesforce, it’s gonna happen.
Or I know, we’ll adopt ABM (account based management) or some other sales methodology.
But those plateaus were stubborn. All of the above promised breakthrough sales but the reality was that nothing delivered them for us.
Maybe this is you. Maybe you are in an early stage and trying to get product-market fit. Or may your business had been growing, but sales are increasingly harder.
After finally getting an exit on my first startup, and then after starting two other businesses, I started to see the blindspots I had that were keeping me from getting sales were I wanted them.
In this week's Rocket Ship Business Academy Podcast, I give you the 4 deadliest sales blindspots. Knowing these blindspots will help you unlock your next level sales. I discuss:
- The essential element that makes all sales go
- How your Founder type is sabotaging your sales
- Why sales plateaus happen
- And….the secret to scaling sales

Ep 14. Scaling Sales - The Missing Step
This week’s podcast episode comes in response to yet another question from my list - and it’s one that’s sure to resonate with many Founders. When asked what their single biggest challenge is, this founder answered:
”Scaling to increase revenue and expand services.”
Scaling sales is a big topic. There’s a ton of information out there on positioning, building funnels, doing cold email outreach, content marketing, consultative selling. In other words, lots of specific tactics.
But just jumping into tactics skips perhaps the MOST important step: defining your ideal customer.
Without this step, all of your strategies and tactics may go to waste.
In this episode, I give you a simple, yet incredibly powerful framework for identifying your ideal customer. I cover:
- Walking you through a powerful ideal customer framework
- How to avoid trying to scale with the wrong customers
- 2 things you probably haven’t considered in defining your ideal customer
- Why narrow and specific is crucial to scaling
- And…an even more powerful way of thinking that breaks through mental blocks on scaling
There is a surprise twist to this exercise, that takes it to an even more powerful place. I’m not going to give away in the podcast episode. However, anybody who listens to the episode and does the exercise can write me at steve@steveaugustcoaching.com and I’ll give you the twist that will create a next level unlock for you!

Ep 13. Is Your Personal Brand Hurting or Helping Your Business?
This week’s episode of Rocket Ship Academy Podcast comes directly from a question from my list:
Should Founders be equally going about building up a personal brand at the same time we are building up our non-personal companies? For instance, my company is a software and digital publishing company. Should I be actively promoting myself (e.g. puff pieces about me in magazines, 40 under 40 list etc), or can I quietly build massive success with no media attention focused on me? So far, I have spoken at tech conferences and I have a speech therapist. But I wonder, should I be doing more to build a personal image as a founder, or does that not matter? Thanks.
This is a great question!
And one that actually brings up one of the most important concepts in building a Rocket Ship business: P&L thinking versus balance sheet thinking.
In this episode, I cover:
- P&L versus Balance Sheet thinking, and how knowing this can radically transform your approach to your business
- How your personal brand as a Founder can be a huge asset to your business…and how it can work against you.
- How to separate nice “pat on the back” personal brand opportunities from ones that will actually help your business
- Why there is no non-personal business
Have a question or challenge you'd like support on? Send to steve@steveaugustcoaching.com and I will do an episode for you!

Ep 12. Why You Aren't Closing Your Prospects (And what to do about it)
”I don't know if it's covid related but prospects that expressed interest are very slow or don't get back to me. How can I get them to respond to my follow ups without feeling like I'm pestering them?”
This week’s Rocket Ship Business Academy Podcast episode comes from a question I got in response to my recent question to my list, “What’s your biggest current challenge?”
When prospects show initial interest but then don’t get back to you, or ghost you, it’s really frustrating. But it’s always giving you some important feedback about something that isn’t working in your sales process.
If you are experiencing this, you are not alone. Growing sales is the single biggest challenge selected by Founders in my Founder Type Quiz.
In this episode, I break down why your prospects are closing - and what you can do to improve your win rate. I’ll cover:
- The number #1 most critical thing to get your prospects to take the next step
- How your Founder type impacts your challenges in selling
- The 3 areas your sales process could be breaking down
- How to follow up without feeling like you are pestering your prospects
- How to feel empowered when selling no matter what the outcome

Ep. 11 Revisiting Bad Decisions
I was in the process of writing my weekly Sunday Steve email for my coaching clients, when I saw an email from one of my clients pop into my inbox, "Are you available today for a quick call today? I need some support in planning our next moves before Monday kicks in."
This Founder is facing some very hard decisions. Decisions that need to be made quickly and involve dramatically shrinking the team. And in this new configuration there didn't appear to be a place for his co-founder. There were a few scenarios on what actions to take but it's pretty clear what needs to be done.
At one point the conversation turned to "bad decisions" made in the past. It's a natural part of the process when you are facing tough decisions to look back and judge the decision path that got you to this point as "bad."
In this episode, I cover:
- How to separate the decisions we make from the outcomes we get
- How to deal with the "should have's" that show up.
- The most important question to ask when evaluating past decisions
- How to win no matter what the outcome

Ep. 10 3 Reasons Your Star Hire Didn't Pan Out
Steve"But they looked great on paper...."
One of the most common challenges I hear Founders facing is a recent hire that didn’t pan out. It’s one of the most frustrating aspects of Founder life. It feels like you spend a ton of energy, time and money only to end up back where you were, having to start over to fill that position.
In this week's episode of the Rocket Ship Business Academy Podcast, I reveal the 3 biggest reasons hires don’t pan out - and what to do to give yourself the best chance of making your next hire a great one.
Topics covered:How to rethink job descriptions to set hires up for success
- Why great interviews can be misleading and what to do instead
- Key warning signs that a hire is not a fit
- 3 simple tests to ensure you are making the best hire possible
Do you have a question you'd like support on? Send your questions to steve@steveaugustcoaching.com and I will answer in an upcoming episode!

Ep. 9 Handcarts, Locomotives and Rocket Ships
In this week's episode I describe the 3 stages of your business: Handcart, Locomotive and Rocket Ship.
Clocking in at insight-packed 12 minutes, I talk about how your business needs to evolve and how you as a Founder need to evolve with it. Just a few of the learnings I discuss:
1. How to reduce overwhelm by working on the right problems for your stage.
2. Why Handcart to Locomotive stage is the hardest transition to make
3. When Type V and Type E founder really need Type O's and Type B's
4. How to know if your early team will scale to the next stage
5. The one thing you need to focus on at each stage

Ep. 8 The Real Action Is Inside Us
In this episode of the rocket ship business academy. No matter what’s going on in our business, the real action is inside of us.
In this episode, I am reading from my book 33 Meditations for Seed Stage Founders. This is a book I wrote in 2020 when I gave myself a challenge to write a daily meditation on entrepreneurship - based on quotes from philosophers and thinkers who I admired.
This is Meditation #23, and the quote is from Terrance Mckenna. Terence McKenna was an American ethnobotanist and mystic who advocated the responsible use of naturally occurring psychedelic plants.
This quote caught my attention because it spoke to something that has struck over and over again in life and business. No matter what’s going on in our external circumstances, the real action is inside of us.
If you feel like your business is stuck, this episode will give you a surprising path to getting it unstuck.

Ep. 7 The One Number That Will Transform Your Business
As a Founder, you’ve likely learned the important of metrics for your business. The thing is, there are so many metrics to choose from.
There are financial metrics like revenue, gross margin and profit.
There are marketing metrics like CAC and churn.
There are product metrics like Net promoter score and month-over-month growth.
All of these metrics tell you really important things about your business.
But how do you know which to focus on?
What if you could have one metric that everyone could point to and understand instantly how it all fits together?
What if there was one metric that made it simple for everyone in your company to how to focus their thinking and efforts?
Finding this one metric can transform your business.
It exists. I call it the Boss Metric.
And in this week’s episode of the Rocket Ship Business Academy Podcast, I show you how to find it.
This might be the single most impactful episode to date!
PS Do you have a question you'd like support on? Send your questions to steve@steveaugustcoaching.com and I will answer in an upcoming episode!