First customers can be very different

When you get your first paying customers, they are often all over the board. Different segments, different sizes, sometimes different use cases. While this is normal, you want to quickly test which segments have the most must-have problems and you can generate the most value to solve those problems. Keep iterating until you start to see consistency in problem/segment/use case/value that can be a sign of early product-market fit.

Match go-to-market process and solution to ICP

Once you find the right ICP, now you can start building out the go-to-market process. How do you find customers, how do you create awareness, how do you move them through the sales funnel, how do you onboard them, how do you deliver value, and how do you maintain their business. With multiple segments early on, that can complicate the process and divert your resources.

Focus is critical

One thing you don’t have as a startup is time and money. To start building momentum you want to quickly be able to focus on one specific niche in the market where you can solve one problem for an underserved customer segment and be 10x better. If you have too many different ICPs to serve, it is hard to focus and you end up being just average across multiple areas.

Be very crisp on the specific ICP you plan to focus on to start. Keep listening and learning. After you achieve some success in your initial ICP, then eventually you can consider expanding to the next one. But out of the gates be laser focused on one ICP.

Be patient

Patience is really hard for humans. I grew up in a world of be patient and wait your turn (in line, in sports, at work). Even with startups it takes patience iterating through an idea, finding product-market fit, building revenue, and growing to a scaling stage. Now with technology and resources, the time it takes to go from idea to scaling company continues to shrink which makes people less patient. While this rapid growth is possible, it can create a knee jerk reaction to not have the patience to work through ideas that are on the right path but just need some tweaking. Stay patient, trust the process, keep learning, and if you build the right foundation on a must-have problem good things can come (it just may take 10+ years for overnight success).

Be humble

I was taught that if you are good you don’t need to tell people, they will see it. Many of the best founders I know are heads down building and working with customers. They are confident and focused on what they are doing and don’t need to constantly show off to everyone how great they are for approval. But there is another world of going to events, winning “awards”, posting on LinkedIn every day, and generating lots of followers. Don’t get me wrong, there can be business value in those things. But remember that alone does not mean you can build a great business. Remember to stay focused on your customers and humbly listen and iterate with their feedback.

Earned vs. expected

I learned early on that life is not fair. Everything you do must be earned and even if you do the right things, that doesn’t mean you get what you deserve (especially in the short term; things even out more over the longer term). Startups are hard, but you have to fight the notion to just expect it to happen: you shouldn’t expect customers to signup just because you have a great idea/tech. You shouldn’t expect to raise money from investors just because you are fundraising and went to an elite school. Keep earning the trust of your customers, investors, and team every day.

The good news is there are many core principles around customer discovery, must-have problems, authentic demand, doing things early that don’t scale, etc. that have and will stand the test of time. But as the old adage goes, the only thing constant in life is change.

You will doubt yourself, keep going

There are many times you will look in the mirror and doubt yourself: your ability to close a deal, to deliver a product, to build the right team, to survive for another six months. Just keep going. It is amazing what can happen when you continue showing up every day, listen and learn, and keep tinkering until you find the right magic.

Things will go wrong - control what you can control

It is a guarantee things will go wrong. But I love the quote: life is 10% what happens to you and 90% how you react to it. Acknowledge the problem, find the best path forward, and don’t worry about what you can’t control.

Surround yourself with a great team

Whether it be your spouse, co-founder, team, or investors you want to build a great culture (that you 100% control). That team will help you through the ups and downs, fight through challenges together, and deliver and celebrate key milestones. The people make all the difference.

The reality is doing a startup comes with sacrifices in some other areas of your life. This could involve family relationships, friends, hobbies, etc. that will take a back seat. Make sure you are choosing wisely what you are willing to sacrifice.

Carving Out Time: Embracing Reflection for Business and Life Alignment

We all get busy in the day-to-day grind of running a business, family, and going through life. It is easy to get sucked into an endless list of tasks and lose sight of the big picture. I’ve heard a lot of different approaches to finding this thinking time to see the big picture; here are a few of the ones entrepreneurs and investors I know have found helpful.‍

A space in your daily life

A lot of people have their own time they create in their daily life to reflect. For some it can be exercise (i.e. going for a walk or run), others it can be their morning cup of coffee, riding a lawnmower can be what you need, an evening prayer or meditation, some even leverage time in car/subway/traffic as space to think. Whatever that space is for you, leverage that daily time to prepare and reflect.

A process/structure for reflection

In addition, others use formal tools/processes as a way to force thinking and reflection. Writing a weekly update or Simple Strategic Plan are two good mechanisms to help you reflect on where you are at and where you need to go.

A vacation/unplugging time

It’s easy to get heads down and not find time to unplug. Whether that is going to the beach or mountains or jetting to another city, some folks use this vacation time as a way to recharge and reflect on how things are going.

The most important thing is to make sure you get out of the weeds at regular intervals and take stock on how things are going. There could be a lot of accomplishments to celebrate, some big and necessary changes looming, and/or a simple solution that is already right in front of you. Find the right time and space for you to do this deep thinking to make sure you are on the right course for your business and life.

Principle - Failure can make you stronger

In the book, the author talks about how during SEAL training he was coming in last for swim training. This failure required him to do extra exercises that were punishing. Yet, he slowly began to realize these additional punishments were actually working the muscles and skills he needed to be successful in the swim. He continued to progress in his times until at the last swim drill, he finished first in the group.

He also gives an example of how he struggled to lead a group of SEALs early in his career and was reassigned. The learnings from that failure ultimately helped him become a better leader and position him well for the rest of his career as he learned key lessons from that experience.

For entrepreneurs:

Most traditional school and corporate training teaches us that failure is bad. We are taught how to not make mistakes. For entrepreneurs, failing fast is critical to success.

First, as an entrepreneur you are constantly running lots of experiments to test and learn what works and resonates in the market. Many of those will “fail.” But without that constant testing in the real world, you will never know. Deciding things in a conference room will sound good in theory but miss the real world feedback.

Second, many of the best entrepreneurs I know had a first startup that “failed.” Yet, the learnings they took from that, the chip on their shoulder, and their desire to try again were all critical to their future success.

Lastly, there is a fear you have to overcome to put an idea out there, to launch a product that is not perfect, or to try and close a sale. You can’t be afraid of pushing yourself outside your comfort zone. The best learning and development happens when you are uncomfortable.

Principle 2 - You can’t go it alone

In the book, the author talks about how everything in Navy SEAL training is done in teams. You swim with a partner, you row together in a raft, you participate in drills together. It is all designed to help you learn how to support and rely on teammates in difficult situations.

For entrepreneurs:

Being a solo-founder is incredibly difficult. You need someone to bounce ideas off of, someone to challenge your thinking, someone to support you, and someone to handle the things you are not as good at.

This could mean finding the right co-founder that can balance your strengths and also match your core values. This could mean finding the right teammates who share an owner’s mentality and work ethic to help you build a great culture. This could mean finding the right community to support you with peers, mentors, and programs. This could mean finding the right advisors/investors who can open doors and support you along the way through some of the difficult times.

On the flip side, the wrong teammates can be a drain on you and the business. Make sure you find the right people to be on your team.

Principle #1: Start your day with a task completed

The author talks about how every morning when the soldiers woke up, they were required to make their bed perfectly. He elaborates on how the beds were then inspected to ensure every detail was taken care of. You would start your day with a task completed. Then even if you had a terrible day, when you returned home you would see your bed was made and be reminded you had accomplished something.

Making your bed is something you alone completely control (not subject to external forces). Doing little things right every day creates good habits.

For entrepreneurs:

Little things lead to big things. Good habits of doing little things right help prepare you to tackle the inevitable bigger, harder problems. If you can’t do the little things right, you likely won’t be able to accomplish the bigger ones. You can’t just build a product on day one that solves your massive vision. You have to work with the team and customers every day to keep iterating. Solve one thing, move on to the next thing. Over time, all of those little learnings and iterations lead you to solving the big problem.

Another variant of this is accomplish one key to-do first thing in the morning. This is often when you are most fresh, can block time, and can then know you have already accomplished something important at the beginning of the day.

Consistently doing the little things like speaking to customers, supporting your team, and iterating the solution to better solve a must-have problem create a strong foundation on which to have success with your startup.

Zero time spent tuning message

It takes <30 seconds to add some level of personalization: our firm name, how their business aligns with our thesis, they are local to Atlanta, etc. Most forms we receive do not. This is an easy way to stand out from the noise.

Not a company email

When an entrepreneur asks for funding with a personal email (i.e. gmail), it questions why they have not felt convicted enough about their idea to get a domain for their business. Even worse if the personal email is AOL or Hotmail : )

Stealth mode

There are very few instances where being in stealth mode is actually helpful. It usually delays the learnings and feedback required early on to pivot your business into the right solution. Somebody somewhere else in the world has the same idea; it is all about execution.

Overused buzzwords

When I read self described words like “innovative” or “disruptive”, or comments like “we have no competition” that raises red flags. Choose your words carefully.

Require NDAs

For reasons previously mentioned, most VCs can’t sign NDAs. If you are asking for one that is an immediate pass.

Generic AI automation or templated without thought

I am seeing way more “poor AI personalized” outreaches that are following logical templates to make it seem personalized, but miss the mark. For example, it may reference I saw you invested in Company X so we thought this might be a good fit. In reality, Company X was an investment 10 years ago in a totally different space. Or I see you invest in [insert thesis] that actually has nothing to do with our thesis. It is best to reality check the tools you are using.

I still read every inbound form that comes through our website, but only respond to ones that show a level of effort and a genuine desire to learn and be supported versus just wanting money.

Entire grape

When does it make sense to keep bootstrapping and maintain 100% ownership versus raising outside capital:

• For entrepreneurs who want to maintain complete control over all their business decisions

• If you believe additional capital doesn’t help you grow faster

• If you are already profitable and can self fund growth

• If you are uncertain on market size, and want to maintain optionality for earlier acquisition opportunities

Slice of a watermelon

When does it make sense to raise money and be diluted to a slice of a bigger opportunity:

• When you believe in a big market and going fast to get there

• When you have proven early traction and want to do more of what you know already works

• When you have found the right investors that can accelerate your business

There is no right answer to which is better. The math can work for any size grape or watermelon:

100% of $20M = $20M

20% of $100M = $20M

10% of $200M = $20M

It is very rare to own an entire watermelon - so do you believe you have an opportunity big enough to be a watermelon, or do you believe you may have a grape?

Givers

There are many great people in the startup ecosystem who try to give to others. They can give with their time, their advice, or their support. They genuinely want to be helpful and are not looking for anything in return. At Atlanta Tech Village we call it “pay it forward.” These are good people to listen to because they have your best interest in mind and want to see you succeed.

Takers

On the opposite side, there are people who are focused on what they want and it is all about them. They may try and take your time, your ideas, or your money. There are “brokers” who try to make you pay them in exchange for capital connections. There are “advisors” who want you to pay them first before they prove any value. There are “connectors” who connect with you on LinkedIn and then instantly try and sell you something. There is definitely time for a proper exchange and partnership, but be careful of takers who lead with that from the beginning. It usually ends up as a transactional relationship; that may be fine in certain situations (i.e. sales commission deals). In the end, takers are focused on what is best for them (and not you) and will turn when there are any bumps in the road.

Another subtle trick is that givers often spend a conversation listening to try and understand how to be helpful. Takers spend most of the conversation talking about what they want to talk about that will further their objectives.

If you want to impress investors and scale effectively, you need to start showing real momentum. Here is how to level up your metrics at every stage.

1. The Idea Stage: From “Liking” to “Learning”

The Trap: Many founders claim traction because “everyone loves the idea.”

The Reality Check: Most people are just being polite (read The Mom Test to understand why). Positive feedback isn’t traction.

The Level-Up: Don’t tell me people like the concept. Tell me you’ve had 50+ deep-dive discovery calls. Better yet, show me design partners who are so desperate to solve a problem that they are willing to pay you to build the MVP.

2. The Early Stage: From “Interest” to “Intensity”

The Trap: Relying on a “huge pipeline,” verbal commitments, or non-binding Letters of Intent (LOIs).

The Reality Check: A pipeline is a promise, not a proof point. Deals fall through, and verbals don’t pay the bills.

The Level-Up: Focus on conversion and retention. Show me passionate, paying customers who have already renewed or, even better, referred their peers. Traction at this stage is proving that your product is “sticky” and essential.

3. The Growth Stage: From “Founder led” to “Accelerated”

The Trap: Reaching $1M in revenue with “zero spend on sales and marketing.”

The Reality Check: While impressive and important, “founder led” growth is unscalable. It usually means you’ve proven this can work, but you don’t yet have a “machine.”

The Level-Up: Investors want to see a repeatable Go-To-Market (GTM) playbook. Show that you’ve tested specific channels, know your Customer Acquisition Cost (CAC), and understand exactly how $1 of investment turns into $3 of revenue.

The Bottom Line

Traction isn’t about how hard you’re working; it’s about how much “proof” you’ve gathered. Make sure you aren’t just moving; make sure you’re moving the needle that actually matters for your stage.

As a founder, it’s easy to get trapped in the “garage phase,” but if you want to scale, you have to get in the flow. Here is why stepping out of your office is a strategic move for your business:

1. Rapid-Fire Peer Learning

There is a unique chemical reaction that happens when you hear how another founder tackled a problem. Maybe they pioneered a lean go-to-market strategy that cuts your customer acquisition cost in half, or solved a technical bottleneck that has been stalling your dev team for weeks. When you expose yourself to diverse business models (even those outside your industry) you gain a library of lessons learned without having to pay the price of making those mistakes yourself.

2. Stress-Test Your Vision

It’s easy to feel like a genius when you’re the only one looking at your pitch deck. The moment you “get in the flow” and put your idea in front of others, the real work begins. The skeptical questions and pushback you receive aren’t obstacles, they are a roadmap. Every “Why would a customer want this?” or “How do you scale that?” forces you to refine your logic. Better answers lead to a more resilient business.

3. Build the Well Before You’re Thirsty

Building a startup in isolation is hard. You shouldn’t be meeting investors or potential co-founders for the first time on the day you need a check or a hire. Get into the ecosystem early to build genuine social capital. Beyond the logistics, the psychological boost of being around people who “get it” is the best antidote to the inevitable loneliness of the founder journey.

How to Start

Whether it’s a session at Atlanta Tech Village or an industry meetup, find where the builders in your city congregate. If you’re just starting out, stop polishing your slides and start getting in the flow.

Your next big breakthrough is likely sitting in a room you haven’t entered yet.

Watching them work, I was struck by a clear realization: the rigor required to be a great investor has many parallels to the rigor required to be a world-class founder. Whether you are writing the check or building the product, these three skills are non-negotiable.

1. Customer Conversations Over Desk Research

You can’t understand a market from a spreadsheet. For founders, constant customer discovery is the only way to ensure you’re solving a real pain point. For investors, talking to potential users is the only way to validate if a “vision” aligns with market reality. Desk research provides the map, but talking to customers tells you what’s actually happening on the ground.

2. Anticipating the “Wrong” Forecast

In my experience, the only certainty about a financial forecast is that it will be wrong. Founders must prepare for “Scenario B” and “Scenario C” so they aren’t paralyzed when the market shifts. Similarly, investors must model both the “moonshot” potential and the catastrophic risks. Resilience comes from being prepared for the outcomes you didn’t plan for.

3. Cultivating the Unique Insight

The best founders see a gap in the market that others ignore. If an investor only chases the deals that everyone else loves, they’ll overpay for average returns. I was told early in my career: If people don’t think you’re crazy on 30-40% of your deals, you aren’t taking enough risk. True alpha—in building or investing—comes from unique insights that the consensus hasn’t caught onto yet.

This overlap is exactly why many of the best investors started as entrepreneurs. They aren’t just looking at numbers; they’re looking for the traits they once needed to survive.

What other skills do you think belong on both sides of the cap table?

We are big fans of lines, not dots. Investors don’t want a snapshot; they want to see your trajectory over time. Here is how to build that momentum.

1. When to reach out: Earlier than you think

The best time to talk to an investor is when you don’t need their money.

• The Strategy: Reach out while you’re still building. Seek their advice on specific industry hurdles or functional expertise.

• The Goal: Share your “next steps.” When you follow up three months later, you can prove you actually executed those steps. This demonstrates coachability and speed—the two things investors crave most.

2. How to reach out: Use the right door

Not all entry points are equal. In order of effectiveness:

• The Warm Intro: A recommendation from a founder they’ve already funded is gold.

• The Event: Meet them in the wild. It’s the easiest way to gauge chemistry and learn in a low-pressure environment.

• Cold Outreach: If you go this route, be brief, data-driven, and specific about why they are a fit for you.

3. The Objective: Build a relationship, not a bank account

Your first goal isn’t a check; it’s a connection.

• Reliability: Do what you say you’re going to do.

• Consistency: Keep them updated on milestones over time.

By the time you’re officially “fundraising,” you won’t be a stranger with a pitch deck—you’ll be a proven founder with a track record they’ve seen with their own eyes. Once you get into fundraising, there are other questions to ask an investor, preparing for the pitch, themes to nail, etc. But first, build the relationship.

If you’re feeling the weight of the “middle years” in your business, remember these three lessons from this year’s Masters:

1. Expect the “15-Minute Flip”

Rory held the largest 36-hole lead in Masters history, lost it, fell behind, and then stormed back. In a startup, you can go from “closing a seed round” to “catastrophic tech failure” in the span of a lunch break. The “ups” aren’t a sign you’ve arrived, and the “downs” aren’t a sign you’re finished. They are simply the price of admission.

2. The path might not be what you expected

By 2014, Rory was the golden boy with four majors early in his career. He probably didn’t plan on a decade-long wait for a Green Jacket, followed by a second the next year. We often get blinded by “startup theater”—the polished stories of linear growth and easy exits published on LinkedIn and news articles. The reality? The path is a jagged mess. Success isn’t about avoiding the detour; it’s about surviving knowing there are multiple paths to success, and it might not be the path you envisioned.

3. Patience is a Competitive Advantage

Mental toughness isn’t born in the winner’s circle; it’s built on the practice range when no one is watching. Rory didn’t “blow up” when his lead evaporated because his preparation provided a floor for his performance. For founders, the “grind” isn’t just about hard work—it’s about staying patient enough to let your unique insights finally catch fire.

The Bottom Line:

Whether you’re chasing a major or a market-cap milestone, the strategy is the same: Stay in the game long enough to get lucky, and work hard enough to capitalize when you do.

Stubborn on one nice-to-have idea

I have met some founders that stay stuck on one idea. They either don’t solicit enough feedback to hear why customers do not like it, or they don’t follow The Mom Test and just hear everyone say they like the idea and believe it. They tend to ignore feedback that contradicts what they want to hear. There are great founders that sometimes get stuck on one nice-to-have idea and miss the huge opportunity cost of moving on to a better market/problem.

New idea every month

On the other extreme, I meet some founders who are pitching me a new idea every month. Each time they move past what they learned about the previous idea to quickly tell me why this is the next big thing. The cycle then repeats again and again. For these founders, it is hard to distinguish what is real versus chasing the next shiny object without focus or the commitment to deep understanding of a space.

Ideal balance

Pivots are required to build a business. But what are you really learning that shows you can go deep to truly understand the problem/market/customers and then also apply those learnings to whether you stop, pivot, or keep going? Many of the best founders we worked with had previous startups that did not work out. That can be great, assuming you can acquire and apply those learnings into your next startup idea.

I love hearing the insights founders have gained at each stage to drive their decisions. Insights from talking to potential customers are the best kind! So pivoting ideas is a likely scenario; just be careful staying stubborn on one idea or jumping too quickly between ideas without spending the time to go deep.

Information now

We live in a world where you can get answers to questions instantaneously. Given that, why would an entrepreneur want to wait to schedule time to speak with an investor or attend an event in the future? The hope is that by making a digital twin available 24-7, anyone in the world can get answers to their questions in real time. The twin never sleeps : )

Common patterns

Given we see many common types of questions and answers, we thought it would be relatively easy to tap into those responses. During a typical Office Hours event, we almost always end up discussing topics like The Mom Test, don’t build too much too soon, get passionate, paying customers, meet with investors before you are fundraising, etc. If there are many common threads, let’s find a way to make those available and shared with more entrepreneurs.

How did the first test run go?

The digital twin nailed some of the questions, some it got part right but could have added more related commentary, and some were funny in the tone and style it used to respond. Naturally it did better at some of the more common questions than nuanced questions. It also responded better to general advice than specific questions about a company or product. But as with anything in the startup world, better to test an imperfect solution early than wait too long building the “perfect” twin (that will never be perfect).

The digital twin is getting better and still improving. If you would like to check out a working version of my digital twin, feel free to do so here. Would love your feedback on how to make it better!

Novel idea

Some people assume you need a novel idea to have a successful startup. Some of the largest companies were not the first (i.e. Google was not the first search engine). There are also many great companies that execute really well on a “boring” idea. What is important is that the entrepreneur finds a space and a problem they are passionate about.

Unique insight

Within your space, you do want to look for what I have heard coined “a unique insight.” This insight could be a customer segment that is underserved, a long held truth that has changed, a unique go-to-market approach, a focused and simplified product on what really matters, etc. But in all of these scenarios, the entrepreneur has found a different way of looking at the world that helps them stand out for their target audience (and likely pushes away non ideal customers).

How to find

While you may have some previous expertise in the market, nothing beats getting out and talking to potential customers. Here are two examples of things I listen for: a potential customer is using a service they hate, but still pays for it because that is the best that is out there and it is mission critical. Or the market has gotten full of legacy competitors with bloated/feature heavy products that have driven up the price and are cumbersome to use … how can you simplify the offering to a small set of things that people will pay for?

So while you don’t need a novel idea, it is worth talking to potential customers and finding out what is your unique insight through which you can focus and get started in a niche of a bigger market.

What path do you want?

Some entrepreneurs want full control. Some want a lifestyle business. Some want to grow as big and fast as they can. Only the entrepreneur can define their vision and path. However, what path you want will dictate if raising money makes sense. If you want full control and optionality to sell when you want - consider bootstrapping. If you see a massive market opportunity you want to quickly go after - consider raising money.

What are you using the money for?

A simple framework I like is: are you using the money to do more of what already is working - if so that can be a good use of money. If you are using the money to figure something out - be careful as that often burns money on an unclear timeline. I also prefer money towards sales & marketing purposes that have already been proven in early stages. Raising a lot of money for product/tech in the “build it and they will come” model carries a lot of risk.

Who is the investor?

Money is a commodity. Having the right investor on board can be a huge boost for an entrepreneur (conversely the wrong investor can be a huge drain). If you find the right investor, that can push the entrepreneur to raise some money to bring the investor on board. But be careful just taking money from anyone.

In general, we prefer bootstrapping early while you are still figuring things out. Once you get some early traction and have a better idea of what the end vision is, then evaluating fundraising paths can make more sense. Early on we encourage maintaining optionality versus committing to a path where it is still uncertain the potential outcome. Remember you can still fund your business without raising money.

Not just users or paying customers

Just because a customer buys my solution doesn’t mean PMF. How do they use it, what value do they get, will they renew? A great question out there to ask is “how would you feel if you could no longer use [product x]? Essentially, how disappointed would they be if the product went away. Obviously the more disappointed, the better sign of PMF.

Consistency

The above may be for one customer, but do you see the same thing across multiple customers? Do those customers have the same problem, the same profile, the same use case, and get the same value? When you start seeing consistency in the problem, ideal customer, use case, and value proposition that is a good sign of PMF.

Other dimensions

Now that you have some consistency above, how does your go-to-market strategy work and are there signs of a repeatable process? Can you find your ideal customers, bring them into the funnel, get consideration, close the deal, onboard them, and deliver the value? The more repeatable the process, the more likely you will be to achieve PMF and capitalize on the growth opportunities ahead.

The PMF term gets thrown around very easily. Make sure you have consistency with your customers first before really trying to scale up. Also, know that PMF changes over time so just because you have PMF today doesn’t mean you don’t need to adjust in the future.