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Aug
13
4
min

Why Good Revenue Can Hide A Bad Business

Almost every founder I know has learned this lesson the hard way.

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Almost every founder I know has learned this lesson the hard way:

Revenue growth doesn’t guarantee a great business.

Revenue growth is essential to a great business.

But it’s not the only factor.

If you’re a founder who:

  • hired too many people

  • realized that a line of business or customer segment wasn’t profitable

  • had expenses balloon without realizing it

  • missed a sales target and had to do layoffs

You know the pain of having revenue growth with the underlying business being in a bad spot.

Here’s the thing:

It’s not just you.

I know 100s, maybe 1000s of stories like this.

Including from founders who have gone on to become millionaires and even billionaires!

It is an extremely painful but wildly common lesson. It’s learned the hard way, but you only need to learn it once!


Why It Happens

It usually involves most or all of these factors!

  • You’re growing quickly.

  • You’re focused on sales and customers.

  • There’s a million fires to put out daily.

  • It can be hard to get a clear financial picture because expenses, cash flow, and revenue vary from month to month.

  • You don’t know yet what metrics (and leading indicators) matter most to your business.

  • Competitors are scaling quickly (or so it seems).

  • Revenue is growing so of course everything is okay!

P.S. This can happen with personal finances too! Anyone ever overspend at their first job or pay raise before realizing you can’t actually afford a fancy new car or dinner out every night on an entry level salary even though it IS more money than you’ve ever seen in your life?!?


What To Do

If this is hitting a little close to home, here’s the action plan:

Get to a good place as quick as possible.

What does “a good place” mean?

It can vary depending on the business and situation but usually involves some mix of:

  • Get clear and honest about the financial reality (margin, cash flow, runway)

  • Make the cuts needed (people or expenses)

  • Get to breakeven, profitability, or extend runway

  • Pivot or end-of-life a product that’s not working

  • Fire a bad customer (said politely: wind down a customer engagement that doesn’t serve the business)

I know multiple founders who have looked into the abyss, made the hard decisions, and their businesses went on to thrive.

I also know founders who realized their business had a mortal wound, closed things down in an honest way, and started again with something wildly successful.

In both scenarios, the scar tissue sticks with you. It doesn’t feel good but it makes you a better entrepreneur long term!


How To Prevent It

If you’re one of the rare founders who hasn’t experienced this first hand or you’re just getting started, here’s what to remember:

1. Look Beyond Revenue

Most founders I know have an eagle eye on revenue. They can tell you their current ARR, # of customers, and the size of the last deal that came in.

They may even check their bank account balances regularly.

The key is to go deeper.

  • What is your sales pipeline like?

  • How many months of runway do you have?

  • What is your cost of customer acquisition (CAC) or life time value of a customer (LTV)?

  • Does your hiring plan align with revenue (and cash flow)?

These “second layer” metrics can often reveal business weaknesses or financial issues on the horizon.

2. Stay Close To The Numbers

Founders are busy. Overloaded and overwhelmed. So is your scrappy startup team.

What’s more important — closing a new deal or logging expenses in Quickbooks?

Would you rather dedicate resources to customers or back office? Customers, of course!

A few months of frenetic customer activity and you realize you haven’t looked at financial data in weeks. Gulp.

Or maybe someone sent you a summary but you didn’t have a chance to really dig in and ask questions.

This is one reason why companies have quarterly board meetings and send weekly or monthly updates — accountability.

It’s a forcing function to organize, review, understand, and analyze the financial and business data.

If you don’t have investors or advisors, figure out other ways to build in checkpoints for yourself:

  • Non-negotiable calendar block

  • Hire a part-time bookkeeper, meet regularly

  • Create a CEO peer group for financial accountability and learning

  • Bring on a fractional CFO

When you stay close to the numbers, you get ahead of financial issues and better understand the nuances of your business.


What is a key metric for your business (beyond revenue) that gives a clear picture of business health? What strategies do you use to stay close to the numbers? Have you ever had to “reset” a business? What did you learn from it?


P.S. Would you be interested in another post where I go into detail on “secondary metrics” and other strategies to monitor business health? Reply or comment to let me know!

August 13, 2025
Aug
5
4
min

Investor-Approved ATL Events (Mark Your Calendar!)

Don't miss these events (and key deadlines)!

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Kids in Atlanta are heading back to school which can only mean one thing…terrible traffic. 🥴

On the bright side, the fall startup events calendar is packed!

Goodbye vacations and summer camps, hellooooo human interaction and company-building!

Here are a few that I’ll be hosting, attending, am excited about, or all of the above.

Will you be there? Shoot me a note! What’s your fave kind of networking?

Please add other events in the comments!


1. Venture Atlanta

📅 Wed, Oct 15 - Thu, Oct 16
📍Woodruff Arts Center

**FOUNDER PSA** → APPLY TO PITCH BY FRIDAY, AUGUST 8.

Venture Atlanta is the largest venture conference in the Southeast. (Prepare yourself.)

It’s a great place for a scrappy startup to meet investors or get customers. (My best startup conference tips.)

Want to host an auxiliary event? It’s not too late but you need to start yesterday!

#protip: the Founder Funder Jog (see below 😉) was a blast last year!


2. Atlanta Startup Awards

📅 Thu, Oct 9, kicking off InnovATL
🎟 Early bird tickets on sale in Aug

If you are reading this from Metro Atlanta, you or someone you know deserves a Startup Award!

**FOUNDER PSA #2** → NOMINATIONS DUE BY SUN, AUG 10!

Here’s a sampling of awards categories:

  • Best New Startup

  • Best On-Campus Startup

  • Best Underrepresented-Founded Startup

  • Best B2B Startup

  • Best B2C Startup

  • Best Startup for Good

  • Startup Mentor of the Year

  • Community Builder of the Year

  • Investor of the Year

(Last year’s winners for inspiration!🏆)


3. Create-X Demo Day

📅 Thu, Aug 28, 5-7p
📍Exhibition Hall, Georgia Tech

What do you get when you combine the talented students of Georgia Tech, amazing startup mentors, and a tried-and-true entrepreneurship curriculum?!?

The 8th cohort of Create-X!

Fully expecting to meet the next Atlanta unicorn somewhere on demo floor.


4. Atlanta Healthcare Entrepreneur Meetup

📅 Wed, Aug 20, 9-10a
📍Virtual

Join us (from anywhere) to meet other founders, techies, healthcare professionals and hear about these amazing companies:

COMING SOON: *In-person* Healthcare Meetup on Wed, Oct 29, 8:30-10a at Atlanta Tech Village Buckhead! Check back here for more info and registration.


5. Modular 2025

📅 Wed, Oct 22
📍The Eastern

One day summit for brand leaders and storytellers…featuring Andrew Huberman and Casey Neistat!?! 🙌 🤯💪

Hosted by AdPipe (we’re investors), the event will be a masterclass on authentic video storytelling with AI.

Is this an amazing topic where I’ll learn a ton? YES.

Is AdPipe an incredible company on the forefront of AI? YES.

Am I a wellness nerd who can’t wait to hear Huberman in person?!? YOU KNOW IT.


6a. Founder + Funder Jog (Sweaty August Edition)

📅 Thu, Aug 28, 6:45a
📍Tech Square - Biltmore Ballrooms

Don’t miss your chance to try to beat me as the sweatiest-person-of-all-time!

Join us for a leisurely 3.5-4 mile jog around Peidmont Park with other founders, investors, and startup folks.

Huge thank you to Katie Begando, Denis Cranstoun, and Julie Pierre for hosting. 🙏🙏🙏

Very friendly, lots of selfie stops and shortcuts, with coffee (and water 🥵) at the end.

P.S. If you’re a founder in the human performance space and would like to be featured or promo a product during the event, reply to this post or reach out to Katie Begando!

6b. Founder + Funder Jog (Venture Atlanta Edition)

📅 Wed, Oct 15, 6:45a
📍Starling Hotel

A 5 year tradition!

Kick off Day 1 of Venture Atlanta with the ultimate multitask:

  • 4 mile run

  • networking with founders and investors

It’s a great way to get to know folks before heading to the big dance.


7. Pitch Practice

📅 1st & 3rd Fridays, 1p
📍Atlanta Tech Village - Buckhead

📅 1st Tuesday, 1:30p
📍Atlanta Tech Village - Sylvan

Led by the brilliant Jacey Cadet, get *FREE* help on your startup pitch!

Register for the session that works best for you here.


8. Office Hours with Atlanta Ventures

📅 Thu, Aug 14, 12p
📅 Thu, Sep 11, 12p
📍Virtual

Join me and fellow Atlanta Ventures partner, A.T. Gimbel, for an informal Q&A sesh.

Common topics include fundraising, product development, how to get early customers, what we look for when investing, and more!

We do these every month. Check out future dates on the Atlanta Ventures events page.


9. InnovATL

📅 October
📍All Over Atlanta!

The most exhausting exciting month of the year!

In case you didn’t already pick up on this, October is an Atlanta innovation bonanza — and that’s not a coincidence.

It’s InnovATL!

Awards, demo days, pitch competitions, Venture Atlanta, and sooooo much more!

Specific events and schedule are being finalized now so check back to get the latest.


What Else??

Did I miss something? Of course I did! I can never capture all that’s going on in this bustling startup world!

Here are some of my favorite event calendars:

And even more — a list of my favorite resources, groups, and tactics for getting a pulse on Atlanta and finding other tech folks.


Please feel free to drop other upcoming events with details and registration links in the comments below! 👇

August 5, 2025
Jul
29
4
min

5 Sneaky Time Wasters That Slow Down Founders

The most valuable resource at a startup is not money.

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The most valuable resource at a startup is not money.

It’s time! Focus! Energy!

Founders are amazing at making shit happen, finding creative solutions, and seeing opportunities.

This also means — like all humans with big ole brains — they can get distracted.

Or also — like all humans doing hard things — they procrastinate (in ways that feel “productive”).

BEWARE, FOUNDERS!

Here are 5 things that I often see founders waste time on - don’t let this be you!

The work you are doing is too important to get sucked into this crap! 😉


1. General Networking

Going to very targeted events where your potential customers are? YES!

Going to every single networking event? Please no!

It can be fun and feel productive. And of course, “you never know who you might run into.”

But everything is a tradeoff.

Time at events is time away from product, sales, customers.

Like Mark Suster said so eloquently: Don’t Become A Conference Ho.

Here’s a dirty secret.

The people at events? They are rarely the target invite list. They are often people who sell to that target invite list (or job seekers). The most common attendees at a “founder” event are lawyers, development agencies, and, yes, investors. 😉


2. Product Perfection

I had a CEO tell me that the best code he’s ever seen was for a company that never shipped their product.

Perfect code, no feedback, zero customers.

If your product doesn’t have warts, if you’re not embarrassed by your MVP, if you don’t vomit in your mouth when you look at the UI, you’re waiting too long!

Most products are rebuilt entirely from v.1.

Either it was the right thing but not scalable.

Or the wrong thing and you iterate.

Building a product is fun!

Putting a product into the hands of customers to see their reaction is hard!

What if they think your baby is ugly?!?

Avoid the trap of building a great product in your head.

Get a mediocre product into the world and see what happens.

The only way to a great product is by starting with a not-great one!


3. Worrying About Haters

If you have haters, you know you’ve made it!

Critics, naysayers, and trolls…DO NOT EXPEND PRECIOUS EMOTIONAL ENERGY ON THEM.

And definitely don’t spend time arguing or fighting back.

You could be spending time on customers!

Also, when you give it airtime in your head or by replying, you give them power they don’t deserve.

It’s like recognizing a competitor smaller than you. Rule #1 in business PR strategy and ninja black ops mind games is always compare yourself to larger competitors but never mention smaller ones.

Of course, if you’re getting a lot of angry feedback, that may be a helpful data point. Is there anything to learn? Is there a kernel of truth to address?

This also takes the sting out because, boy, was it helpful to have a chance to self-reflect! Thank you, troll friends, for this growth opportunity!

(P.S. Angry feedback from customers is a good sign and shouldn’t be treated as haterade!)


4. Research

ChatGPT for 10 minutes. Up to an hour.

Then get started.

Take an action.

The best way to learn is to get started, put something out there, try it, run an experiment.

The sooner you get started, the sooner you can start not sucking. (Being bad at something is the first step of learning!)

If you are “doing market research” for too long, you won’t be successful. You’re using the research to procrastinate and avoid action.

You can only really truly learn by doing.

I had a million ideas of what this blog should be but I made more progress writing and publishing ONE BLOG than spending 3 months thinking about it.

If you need inspiration, I love Rachel Ledbetter’s post on walking confidently in the wrong direction. She is the founder of Motivo (featured with InpharmD in one of my favorite Healthcare Entrepreneur Meetups ever) and her Substack is fantastic.


5. Non-Revenue Generating Activities

Is this it’s own category or just a summary of everything I listed above??

Obvious-But-Important Reminder: prioritize the things that make money!

It is easier to tweak a website, reply to LinkedIn comments, or grab a cup of coffee than to do cold outreach to potential customers.

It’s more fun to brainstorm campaign ideas than launch one.

But the most fun of all (in the long run) — is to do the hard shit to build a great company!

No one is ever sorry they focused on revenue.

(Unless it makes your culture terrible, in which case, I have some suggestions for you here and here!)

Mo Bunnell and Tim Ferris both have great suggestions for daily practices to do the Most Important Thing. If you’re feeling overwhelmed, you can also use this priority matrix or Eisenhower’s Quadrant.


What helps you stay on track? What did you think would help your company but was a waste of time? What is your favorite cat video? (JUST KIDDING! Please don’t look up cat videos.)

July 29, 2025
Jul
22
4
min

4 Things We've Learned In The Atlanta Ventures Studio

We love starting companies from scratch -- here's the unexpected strategies that work!

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We love starting companies from scratch in the Atlanta Ventures Studio.

We partner with amazing founders to explore big markets, do extensive customer discovery, find authentic demand, and launch a billion dollar business (hopefully 😉).

The Perlant and Undaunted are two examples from this year. Salesloft, Terminus, Rigor, Greenzie, Zinnia, and Intown Golf Club are some others you may know!

We’re always learning but we’ve also seen a lot of at-bats in the 0-to-1 phase of company building.

Here are 4 (counter-intuitive??) things we’ve learned that may be helpful to other founders early in their journey!


1. Spend A LOT More Time In Ideation

Founders are action-oriented and highly motivated. It’s natural to get excited and go all in on an idea.

  • But is it a great idea?

  • How long did you spend exploring other ideas?

  • Is this idea worthy of the next 10 years of your life???

Extra time in the idea phase pays dividends long term!

Most founders are in a hurry to get started so they jump at the first decent idea.

But discovering a great idea takes time.

Even if recognizing the greatness of an idea happens quickly (“I know this is The One.”), cultivating the discernment to spot a great idea comes from experiencing good or okay ideas.

IN THE STUDIO:
Studio Entrepreneurs usually spend 3-4 months up to a year deep diving on different ideas and markets. This includes market research, customer discovery, experiments, consulting, and any number of other idea-phase activities. Action helps refine ideas!


2. Do Different Customer Discovery

I used to think customer discovery was explaining your idea and getting feedback.

THIS IS WRONG!

(It’s not just you. I did this for a decade 🙃)

Something that I learned through the Atlanta Ventures Studio is the importance (and art!) of the right kind of customer discovery.

Have you heard us talk about The Mom Test???

(Only every single Office Hours multiple times…)

Mom Test Takeaways:

  • Don’t pitch your idea at all

  • Ask people/businesses about their problems

  • Find the problems that people can’t stop talking about

  • Understand how much time and money is being spent to solve the problem

  • If no time or money is being spent, it’s not a big enough problem!

  • Notice what people actually do, not what they say they would do in the future

  • Don’t believe positive feedback, only believe actions and credit card info 😉

If someone will pay you, make intros, or spend time with you to help solve this problem, that’s a good sign!

IN THE STUDIO:
The Mom Test is hands down the #1 recommended book by the Atlanta Ventures team and the first book any Studio Entrepreneur reads!


3. Run Experiments

Believe what people do!

We love micro experiments. They are a great way to test demand.

Have a hypothesis going into the experiment. Give it a timeframe and metrics. What does “good” look like? The best experiments get you to a quick yes or no. Maybes are annoying.

If the experiment goes well, it can even be supporting data for a fundraise!

Never ever build anything without running low costs tests beforehand. If you can’t think of how to test, come to Office Hours and we can brainstorm with you!

IN THE STUDIO:
Here’s 7 low-cost, low-effort ways we’ve tested ideas in the Studio and how we’ve tested tech ideas before building tech.


4. The Right Idea Feels “Easy”

The goal of all that customer discovery and experimentation? To find a vein of gold.

We call it authentic demand.

It’s when the market pulls you.

You’ll notice things like:

  • People take your calls.

  • Fundraising goes quickly.

  • Customers sign up even when your product is janky.

  • People refer their friends.

  • You have competition and customers get mad at you 😉

Startups are never “easy” but when you find the right idea, the boulder starts rolling downhill.

IN THE STUDIO:
We love to work with repeat founders. They’ve done it before and are crazy awesome enough to do it again! Something we often hear is, “This company is so much easier than <Previous Company>.” Not every idea is good, not every company works, but when you hit it right, it’s magic!


Any other tips for zero-to-one? What helped you find a great idea? Do you want more lessons learned from the Studio? Or get back to general startup topics??
July 22, 2025
Jul
15
10
min

What Investors Ask, According to AI (and Me, a Real Investor)

30+ Common Investor Questions & What They Actually Mean

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ChatGPT is not funny. I have to write all my #momjokes from scratch.

But it IS really good at generating lists of common investor questions!

These are great questions that I got from using this prompt (also mentioned here):

I am building a startup to automate video production. I am fundraising to raise a seed round. What questions will investors ask me?

As you’re prepping for Q&A (because you know how important it is!!!), these questions are a great starting place.

But what’s a good answer? What do investors care about?

I’ve added some color commentary (literally — my comments are highlighted with a green quote indicator) to give context and helpful hints!


🔮 Vision & Problem

  • What problem are you solving, and why is it important?

Is it a big market? Investors love (and require!) big markets

  • Why now? What has changed in the market or technology that makes this possible?

Something needs to be different. “No one had thought of it yet” is not a good answer. Likely means that it’s not a big enough problem to solve.

  • Who is your ideal customer? How painful is this problem for them?

How painful → put this in terms of $ or metrics!

  • How is this currently being solved today (incumbents, manual methods, etc.)?

Your product is ideally 10x better. People (me included) are lazy and don’t make changes unless something is WAY better.

  • What’s your long-term vision—what does the world look like if you succeed?

It’s hard but important to thread the needle between great long term vision but starting small with a niche/wedge to be successful. You can’t be all things to all people on Day 1 (or ever!).


🛠 Product

  • What exactly does your product do? Can you show me a demo?

Sometimes it’s genuinely hard to understand what the product is/does. Make sure this is clear in your deck without getting into the weeds.

Founders almost always want to demo the product as soon as possible. It’s their baby. “Look at how cute my baby is.”

Most investors want high level info first. They want to confirm the market, traction, and authentic demand. Demo is more of a follow up/due diligence item.

  • What is unique or defensible about your product or tech?

Some investors care about this A LOT. Definitely makes sense in things like med devices, science breakthroughs, etc.

For software companies, we haven’t seen patents or such be that important. Executing well in a fast growing market is key. Other people will also have the idea.

Building a great culture that treats employees and customers well, while being smart about cash, can help you outlast a lot of competitors.

  • How is your product different from existing tools like Descript, Runway, Pictory, or Synthesia?

I love it when a founder knows their competitors well. An answer like, “There’s no one like us in the space” is not good. WHY is there no one like you? Because the market is too small? The best answer is usually something like, “Here’s what others are doing. We agree with XYZ, we think we do ABC better, and we are focused on being the best at 123.” I’d also highlight that it’s a big market and competition is good since there are multiple winners in big markets.

  • What is your roadmap over the next 12–18 months?

Do you know what your customers want? Do you have a plan? Does the plan make sense? This question is both a check to see if the founder has actually thought about how to deploy the capital they are raising, and to make sure they are thinking about product strategically.

Tips on what to build here.

BEWARE: some founders (especially technical ones) get too into “The Product” and how fun it is to build, and lose sight of the customer needs, pain, and budget.

  • What key automation features are you building (e.g., script-to-video, AI editing, avatar generation)?

I don’t know what this question is about other than — are you building something that is 10x better, solves a problem, and is not easy to have a human do?


📈 Traction & Metrics

  • What traction have you achieved to date (revenue, users, pilots)?

Talk about money early and often!!! If you don’t talk about revenue, I think you don’t have any.

And if you don’t have any revenue, here are some tips.

  • Who are your current users or customers?

I like a variation of this — tell me about your best customer. What was the sales process like, why did they buy, how are they using right now? If you get a broad question like this, I’d try to tell stories about specific customers and wins instead of answering it generally.

  • What are your engagement or usage metrics (e.g., videos created per user, churn)?

I like to ask about a specific customer who churned or deal that was lost and why. I want the founder to give me a real answer, showing they know their weak spots and what they need to be diligent about improving.

  • What customer feedback or testimonials have you gathered?

Customer stories!!! Have specifics. Use data and names as much as you can.

  • What’s your GTM strategy—how are you acquiring users today?

Did you get deals through previous relationships? (Not ideal but necessary early on.) Are you running a B2B playbook (BDR, AE, etc) or doing Product Led Growth? Having overall data is great but you can also talk about a specific deal to explain “typical” sales win.



📊 Market & Opportunity

  • What is the size of the market (TAM/SAM/SOM)?

Full rant here. TL;DR — make it realistic (and big!)

  • Is this a niche or a category-defining company? Why?

Category-defining is great because it means BIG. But it can also mean expensive. Educating the market, lots of testing, high legal costs (think: Uber fighting the taxi industry).

Niche can be a great starting place as long as there’s a path to growth over time.

Niche forever? Might be great business but likely not venture scale. Figure out a different path for funding the company…like having customers pay you!

  • Who are your biggest competitors—and why are you different or better?

Know your competitors and be clear on what your strengths are. A good, thoughtful analysis here is impressive.

  • How do you expand over time (e.g., adjacent markets, enterprise use cases)?

Even if it’s pie in the sky, have at least an IDEA of what you will do after you win with your first product or market segment.

Remember: billion dollar companies!!!!


💸 Business Model & Economics

  • How do you make money (pricing model, freemium, SaaS, per video)?

You’d be shocked at how many pitch decks I see that don’t answer this question.

If you don’t talk about your business model…you are signaling that you don’t care about or understand how to make money!!

  • What’s your ACV / LTV / CAC (or your estimates)?

If these numbers are not good — you should be looking at it way harder than an investor! If it takes a ton of money to get a customer and they don’t pay you much…red flag about the long term viability of your business!!

Early on, you may not be tracking this regularly but it’s worth it to calculate these monthly or quarterly. Leading indicators of business health!

  • How scalable is your solution, and what drives margin improvement over time?

Very important especially in non-software businesses like hardware or CPG. Software margins are usually pretty good. If they’re not…figure out why not quickly!

  • Do you have examples of paying customers or pilot conversions?

If you don’t put your revenue in your pitch deck, I assume you don’t have any. Regardless of the typical “advice” given for slide deck order…if you have customers and revenue, talk about that early and often!


👥 Team

  • Why are you the right team to build this?

Don’t be humble. Inspiration here. Reminder: project confidence in your body language also!

  • What’s your team’s background? Who’s technical, who’s product, who’s GTM?

Investors want to make sure that someone can build, someone can sell, and there’s an adult or two in the room.

Having *lots* of big name advisors, that’s usually a turnoff/warning sign. It’s good to have 2-3. But having 20 is a distraction and raises the question, why do you need so much help?

  • Who are your key hires over the next 12 months?

Important to have a rough hiring plan (how are you spending the investment dollars), including self-awareness on team’s strengths and weaknesses.

Also, see if an investor can be helpful on these key hires! “Who do you know in your network?” or “What skill set would you optimize for at our stage?” can be good questions to ask an investor.


💰 Fundraising & Use of Funds

  • How much are you raising, and at what valuation?

Reminder on valuation math: the amount you’re raising implies a 5-7x valuation of that number.

If you’re not getting any interest from investors who would be a good fit for you, it’s possible your valuation is high.

It’s normal for a founder to be optimistic or read the news and expect a big number.

  • What milestones will this round help you reach?

Revenue and customer numbers!

  • How will you allocate the capital (team, product, GTM, infrastructure)?

Raising money should let you pour fuel on the fire, not keep the lights on or add more back office folks. Most investors like to see money spent on adding more sales and marketing firepower or building product faster to get more customers. You’ll naturally need some operations people too but don’t emphasize that.

If you’re raising money so that you as the founder can go full time on your business, I’d make the salary $100k or less. Any more than that and it feels like you don’t “get” a startup. Scrappy at first, creating massive value over time. If you want/need to make a high base salary asap, might not be the right time for a startup!

  • What does your next round look like—when, how much, and what needs to be true to get there?

Where do you go from here? If you raise too much or have a very high valuation, it can be hard to “grow into” your next round. Back of napkin math says you want to double your valuation each round. What revenue $ and grow rate needs to be true for that next valuation? Can you get there with this raise $ and your (REALISTIC) financial model?


🧠 Bonus / Curveballs

  • What’s the biggest risk to this business?

If you don’t know the risks, you’re either lying or an idiot. Sorry, was that too harsh?

A thoughtful answer to this is really compelling. It’s possible the investor has already brought it the top risk. Turn this question around to show how you overcome the risk. You can also ask the investor what they’ve seen from other business or what *they* see as the biggest risk!

Most founders constantly worry about all the ways their company can die while simultaneously being incredibly optimistic. Reminds me of Warren Buffet’s rule #1 — Never Lose Money.

  • What’s the most surprising thing you’ve learned so far?

Gotta be learning and improving. Gotta be open to being wrong. If you haven’t been surprised, you’re not paying attention!

  • If a big tech company wanted to kill you, how would they do it?

Have an answer but also explain why it’s unlikely. 😉 e.g. “Stripe could launch XYZ but they’re focused on ABC.” Or “Salesforce could acquired our competitor but they will quickly move up market and raise prices while we focus on customers, speed, and SMB.”

(P.S. A F500 company acquiring your competitor is not a death sentence. Lots of examples where non-acquired companies still thrived.)

  • Why do users love your product? What would make them leave?

Hopefully you have already talked about your customers loving you 100x before an investor has to ask you this question. 😂

In terms of what would make them leave? It’s usually poor execution by the startup. Maybe you have a better answer but once they are a customer, that’s your deal to lose!


Your Turn

Okay, founders and investors, what’s your unhinged commentary on these questions? Would you add anything? Disagree with anything? What other questions have you gotten? Add to the brain dump below!


Enjoying the O’Daily? Share with a founder!

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July 15, 2025
Jul
8
4
min

Company culture matters, people!!!!

It’s not touchy-feely or nice-to-have.

ICYMI: A strong, positive company culture is a sustainable competitive advantage.

You attract better talent, retain employees, stay more aligned, create customer love, scale faster, and the journey is more enjoyable.

Company culture starts with Core Values.

(Here’s how to figure out your Core Values if you are growing quickly but haven’t defined them yet!)

Once you have Core Values, how do you actually use them to improve hiring, make decisions faster, and maintain high standards?

How do you keep them top-of-mind, fun, authentic, sticky, and personal?

“You MUST do these Core Values or ELSE!” doesn’t usually work that well. 😂

When Rigor announced our revamped, employee-generated Core Values in 2015, we knew we needed to solidify their meaning and presence within the company. Because the team was so involved in the process, we saw great, organic traction right away.

One employee drew “posters” of our Core Values on white boards around the office!

We wanted to continue the momentum and embed it into things large and small, serious and fun, daily and occasional, across the company.

Here’s 7 real life examples of how we incorporated Core Values into the day-to-day experience at Rigor in meaningful ways!

In true startup fashion, you’ll see that most ideas are low or no cost with minimal effort to maintain after a bit of setup.

That’s what I’d call #UsingResourcesWisely! (That will mean something in a second…)


1. #Hashtags

Rigorians started using them as hashtags when we gave shout outs in our team Slack Channel:

It’s simple, free, obvious, and you can #StartToday!


2. Make A Graphic For Each Value

Our designer made a graphic for each value. (Now you’d use AI 😉)

We turned those graphics into:

  • posters

  • pillows (for the lounge couch, duh)

  • Slack emojis

Check out the #WinAsATeam purple trophy:

(See the photo in the Culture Award section for the larger versions!)


3. Culture Award

We started a peer-to-peer Culture Award to recognize Rigorans embodying the Core Values.

The winner of the previous month determines who wins for the next month.

They presented our “Astronaut” (a 3D printed trophy because…I can’t even remember now!) to the new winner at our Monthly All-Hands would explain how they have embodied Rigor Core Values.

The only rule was that it must be given to someone in a different department.

We “borrowed” this idea from Salesloft who gave a pair of Salesloft-branded socks as the prize each month. Highly coveted socks! 😉

Zack Cook winning the Culture Award from Lauren Cabe with CEO Craig Hyde. Core Values on the slide in the background!

4. Review Core Values in All Team Communications

Our Core Values were included and discussed in every Weekly Update (email), Monthly All Hands (presentation), and Quarterly Retreat (offsite).

  • Weekly Update: Each department has a section for Culture shout outs.

  • Monthly All Hands: Review Core Values together & give Culture Award.

  • Quarterly Retreat: Live Core Values by starting the day with community service activity. Highlight how each part of the day represents a Core Value (e.g. #WinAsATeam, #ImproveEveryDay).


5. Include Core Values In Performance Reviews

We added questions about Core Values to our quarterly performance reviews including a performance rating question:

How well is this employee embodying Rigor’s Core Values?

It was weighted the same as the other two performance questions.

If it matters, you need to measure it and hold people accountable!


6. Align Interview Questions To Core Values

We asked specific questions in interviews to understand if a candidate embodied Rigor Core Values.

This portion of the interview was done by someone outside of the candidate’s immediate functional area.

Below is an example of the spreadsheet we used to map Values → Work Expectations → Interview Question.

I highly recommend making a quick matrix with question suggestions aligning to each Value. Otherwise you’ll end up with everyone asking different (and crazy) questions in the name of “culture.” I’ve seen this backfire in big ways that I can’t even share on a blog! 😂


7. Core Values Within Company Policies

We included Core Values to explain the “why” in company policies or how-tos:

We also allocated budget in support of things that aligned with Core Values:

  • Each department had a “Fun Money” budget of $75/employee/quarter to spend on events, team swag, or other culture ideas. #WinAsATeam #ImproveEveryDay

  • Rigor offered a $2500 professional development stipend to enable folks to #ImproveEveryDay and #OwnYourWork.

Here’s the Rigor Customer Success team using our team building budget to do a Toys For Tots adventure in Target with Francis Cordon on Facetime! #DoTheRightThing #WinAsATeam

BONUS: Even More Ideas!

  • Postcards for career fair swag, in-office notes, or sending to remote employees

  • T-shirts

  • Pint glasses - one for each value; collect them all!

  • Welcome Packet for new hires specifically about Core Values

  • Core Value Blogs by employees - pick a value, explain what it means to you with examples of its impact on your work and career

  • Stickers or decals

  • Culture Award wall with winner photos and why they won

  • Company competition with one event or category for each Core Value (could be 1 day or long term, e.g. #DoTheRightThing = # of community service hours as a team)


Does your company have Core Values? How have you implemented them or celebrated them? What fun or creative ideas have you done or heard about??

July 8, 2025
Jun
24
7
min

Finding Your Startup’s Core Values (aka Your Secret Superpower)

Culture is a scaling secret weapon that starts with Core Values.

Read More

Culture is the only sustainable competitive advantage that is completely within the control of the entrepreneur” – David Cummings

Having a great company culture means you can attract better talent, customers have a better experience, employees work harder, and everyone has more fun.

Great culture is not about snacks or massages or swag (though I have enjoyed all of those perks immensely!).

Every great company culture starts with Core Values.

Core Values are the uniting principles of the company.

  • How do we act?

  • What do we care about?

  • What do we look for in others and ourselves?

  • What do we all agree on?

When you have clear, defined Core Values, you can move at super speed with greater cohesion even when growing quickly, facing challenges, or both!

A few examples:

  • It’s a natural vetting mechanism in the hiring process (the right people are attracted to your Values, the wrong people self select out)

  • Employees can make decisions faster using the Core Values as a guide — even when facing new or unknown challenges

  • The team is aligned on what is important and what behavior is desirable

  • Core Values instill a sense of pride and ownership among your team!


Here is the real story — with a step-by-step breakdown, of course — of how we defined our Core Values at Rigor.

(Originally posted on the Atlanta Ventures blog in 2018!)

Like all startup projects, it was relatively simple, low/no cost, and speedy. No consultants or multi-month timelines here!


In 2015, Rigor wanted to clarify its Core Values. We used the Atlanta Ventures values of Positive, Supportive, and Self-Starting for several years. These values were still true but we had evolved a unique personality all our own. With 20 people, our company identity was taking shape and we wanted to put words to it. Here are the 6 steps we took to uncover our Core Values, plus protips and lessons learned for anyone thinking about this process for their own company!

Rigor_Team_Q2_Retreat.jpg
Core Values are more than matching t-shirts. (They look awesome though!) Can you spot pregnant Kathryn??

6 Steps To Uncover Your Company’s Core Values

1. Company-Wide Core Value Survey

Send a company-wide survey asking about personal and professional values. What matters to people? What are their personal values?

WHY?
The survey triggered reflection on the topic of Core Values and we started to articulate what mattered to us.


2. Share Answers

Share the survey responses (without names).

WHY?
This generated awareness among Rigorians about what themes mattered to teammates. Keep it anonymous to prevent any bias and maintain privacy.

Again, you’re getting the wheels turning. Seeing other people’s responses starts to generate ideas for the next step of the process…


3. Small Group Activity

Meet in small, cross-functional groups.

Each group generates a proposal of 3-5 Core Values with short explanations for each.

(~1 hour meeting, follow up via Slack or email on final details, submit within 1-2 days. If there’s not full consensus, that’s okay. Send in the broader list of ideas with context of where people agreed/disagreed.)

“Cross-functional” means a mix of roles, company tenure, personalities, and background.

WHY?
You now have several lists of employee-generated Core Values that resonate with and embody your team. Small groups mean it’s easier to reach agreement. The team has done the “heavy lifting” on the wordsmithing and definitions. Cross-functional means that there’s alignment regardless of role, background, or tenure.

Bonus: It’s an amazing team-building activity!


4. CEO Review & Edit

The CEO reviews all proposed Core Values and edits to 5-8 “finalists” including tweaking language or explanations.

WHY?
The CEO must wholeheartedly agree with the Core Values and feel ownership since they will be driving adoption and leading by example.

If you founded the company, you want the Core Values to be inspirational to you and aligned with your own beliefs!

SPOILER ALERT: Most companies’ culture naturally aligns with the CEO’s personality.


5. CEO Shares “Finalists” & Asks For Feedback

The CEO sends the Core Value “finalists” to the company and asks for 1:1 feedback via email. (No company wide nastygrams please!)

Agree, disagree, favorites, what would you change?

They can also solicit feedback from trusted advisors and company leaders.

WHY?
Sanity check and final feedback. Fine tuning. Letting everyone feel heard.

  • Do these proposed values truly resonate with the team?

  • Did we miss or misinterpret something important?

This step gives your most passionate, invested employees a chance to have a say in the final product. The majority of employees will be happy with any of the 5-7 proposed values but it’s important to listen at every step.

David Cummings did this when deciding Core Values for the Atlanta Tech Village.


6. Announce Core Values!

The CEO announces the final 3-5 Core Values via email, at a company meeting, in person, everywhere.

It’s important to have a sentence or two explaining each value and what it means since a short phase could be open to interpretation.

When you share them in person, include a story or two of someone exemplifying that value!

WHY?
Announce them multiple times across multiple channels. It’s a big deal! You want to remind people, burn them into their brain, emphasize the importance, share them in a way that will resonate for different personalities. Repeating them early and often is the first step of…#7 👇👇


Last but not least…

Defining your Core Values is only the first step. You need to incorporate them into the fabric of the company in a way that feels natural. It takes work and intention to start…then the fly wheel gets going and Core Values reinforce themselves!

More on this in an upcoming post! 😉


#PROTIPS

  • Use your most organized leader to facilitate the process. (**Kathryn raises her hand 🙋‍♀️**)

  • Explain the full process before starting. Clear communication about the process is critical to success!

  • Pre-plan the cross-functional groups. Hopefully there are no mortal enemies on your team but now is not the time to make them work together. It should be a positive experience!

  • Make your Core Values as action-oriented as possible. Core Values like “Own Your Work” or “Use Resources Wisely” are things you “do” rather than be. Encourage measurable actions not inherent qualities.

  • Action-oriented values also provide a framework for decision-making. They help answer questions like, “What should I do in this client situation?”

  • Create a documented version of the Core Values with explanations and definitions. It will be referenced often as you grow. New employees will need context on the Values and it creates one source of truth in case existing employees have different interpretations.

  • Keep ‘em short.

  • Less is more. Rigor had 7 Core Values. We felt strongly about all of them but in a perfect world, it would be no more than 5.


Why It Works

  • Every person in the company participates

  • Trends naturally emerge; no forcing or digging for your Core Values

  • No large group debates (rarely productive) or voting (majority doesn’t mean best overall product)

  • CEO has final say

  • When the values are announced, everyone sees several of “their” values

  • Lots of ideas from lots of places

  • Many ways for someone to contribute within their strengths (email, small group, survey)

  • Pre-work encourages reflection and thoughtfulness

  • Your quietest and loudest employee will both have opportunities to be heard


Fun Surprises

We learned some fun things through this process at Rigor:

  • There were common themes - a lot of folks had similar or overlapping values. In hindsight, it makes sense. We were hiring for certain qualities, we had good team chemistry, we had spoken or unspoken expectations about how to treat customers, each other, the work, etc.

  • Most companies are a reflection of the founder’s personality — especially in the early days. Founders hire people they like who have qualities they respect and value.

  • Everyone enjoyed the process and felt heard!

We were worried that “retrofitting” Core Values could create problems of someone feeling like the Values were “forced” or they didn’t align with the Values. Instead, the opposite was true. We realized that we did have an aligned culture, we just hadn’t put words to it yet!

It quickly became a strength — attracting the right hires, guiding us through decisions, and offering a positive environment with clear expectations!


What are your startup’s Core Values? How did you decide what the Values were? Any lessons to share or advice for other founders?

June 24, 2025
Jun
17
6
min

6 Ways To Avoid The #1 Preventable Mistake In Fundraising

Here’s the mistake I see good founders make when fundraising.

Read More

Here’s the #1 COMPLETELY PREVENTABLE mistake I see good founders make when fundraising:

They are not ready for investor questions.

Their pitch is tight, slide deck is polished, business is solid…and they stumble over the follow up questions.

And not only to do they miss a chance to further reinforce the awesomeness of their business and leadership with good answers, it is a red flag for investors:

“Ah, they were well-coached for the pitch but not actually good at selling, fundraising, strategy, thinking on their feet. In other words, the things you need to be a good startup CEO and leader.”

But like I said, it’s COMPLETELY PREVENTABLE with good preparation!

Here are the 6 strategies to bring your A game to the follow up questions and win the hearts (and wallets) of investors everywhere!


1. It’s the same questions.

Investors are boring business robots creatures of habit. They’ll ask the same questions over and over again. Yes, you’ll get variation. Different firms focus on different things. But you’ll quickly start to see patterns and common topics.

It’s like a job interview. There’s only so many different ways you can ask about someone’s biggest weakness (“caring too much” of course) and why they want to work here (“free snacks” says everyone to themselves but never aloud).

A.T. Gimbel gives a good overview here!


2. Investors will hone in on your weak spots.

Whatever you don’t want to talk about, that’s what investors will ask you.

It’s actually on purpose. Part of an investor’s job is to sniff out the mortal wounds, I mean, risks.

  • Where could this business fail?

  • What is the founder not saying?

  • How much is still unknown/unproven?

It’s tempting to avoid the hard stuff.

Instead, practice that the most!


3. Most things have a positive spin.

A few examples:

  • Did it take you 5 years to get to $100k in revenue? → What incredible resilience! You learned so much about your customers and what (not?) to do in that time.

  • Do you have 1 very large customer and lots of small ones? → Your product solves a problem that affects companies of all sizes.

  • Most of revenue come from partner sales? → Cost-effective and low-overhead GTM strategy; closing deals through partners while building playbook for an in-house sales team

  • Slow sales cycle? → Low churn because companies rarely change vendors; when you win them, it’s a customer for life!

  • Much smaller than competitors → more nimble to adjust to customer and market trends

Now, I’m not saying that if you have a positive spin, you will definitely raise money. Investors may not be swayed or may still pass.

But turning a negative into a positive is an evidence-backed strategy to raise 14x more money!

And, having a great answer to a hard question is a confidence builder and makes pitching fun. You internalize your positive answers, your outlook is contagious, and you may help an investor see things in a different light!


4. Use this AI prompt.

Here’s the thing about lists of possible investor questions. It’s a long list. And investors will usually pick 2-3 questions from that list.

Investors tailor their questions based on:

  • your specific business

  • their investment thesis (stage, what they look for, what their expertise is)

  • what you did/didn’t talk about in your pitch

So there’s no universal list of questions but this list of 30+ questions is a great starting place.

Here’s the AI prompt to get you started:

I am building a startup to <short company description>. I am fundraising to raise <$ amount or type of round>. What questions will investors ask me?

If you have answers prepared for these questions, you’re in a good spot!

I’d also prompt AI for investor questions about <this part of my business that I’m nervous about or feels like a weak spot>.

And of course, ask AI to give you several options on how to answer those questions too!


5. Practice aloud.

Prep your answers. Take notes, write out sentences, use ChatGPT, whatever.

And then…SAY IT ALOUD.

Ideally, with a trusted question-asker who will give you real feedback.

The key to a great answer is not just content. It’s also delivery.

Confident, smooth, concise.

If you are great at those things naturally, congratulations and please message me about writing a guest post. 😂

If you are like the 99.9% of the rest of the world, a few run throughs will make a huge difference!

You still want to meet with your “worst” investors first to further practice and refine, but scheduling time to do several run throughs of Q&A (aloud!) before those first meetings will make a huge difference.


6. Don’t add more to your pitch.

It’s tempting to try to proactively answer questions by including more information in your pitch deck.

FOR THE LOVE OF EVERYTHING, RESIST THIS URGE.

You will go too fast. You will run out of time. It’s confusing. Slides have too much text. It undermines your credibility, the clarity of your message, and your overall ability to communicate.

I once got this great advice about presenting:

If you have an hour to present, plan material for 15 minutes and let the rest be Q&A.

Here’s why:

  • The “audience” (whether it’s a keynote speech or a 1:1 sales meeting) can lead the conversation to what interests them.

  • It’s more efficient, no boredom, no wasted talking!

  • It creates a relationship; it’s a two-way conversation not you talking at someone.

  • You better understand what the audience cares about.

  • People feel special, listen more carefully, and have more buy-in when it’s *their* question.

  • Questions mean learning and engagement. You can’t “zone out” when asking a question.

  • Spoken answers feel more authentic and therefore more trustworthy than a scripted slide deck.

Pay attention the next time someone gives their 4 word elevator pitch. It almost always leads to a follow up question — which is FANTASTIC! Now you can customize the information based on that person’s expertise and interests.

But, Kathryn!?! What about this amazing slide that explains <very complex thing>? The visual helps people understand it so quickly and investors ALWAYS ask about it.

A picture is worth a thousand words.

As a preparer, I love having a slide ready.

Behold: THE APPENDIX

Not your kidney-shaped organ, it’s the catch all section after your pitch where you add slides that may be helpful during Q&A.

Approved by The O’Daily: (quickly!) pulling up a relevant slide from the Appendix during Q&A to better answer a question.


Did you practice answering questions before you pitched? What other tips would you share? Any questions that surprised or stumped you?

June 17, 2025
Jun
10
6
min

One of the most important transitions in a startup journey is when the founder hands off day-to-day selling.

In the beginning, the founder needs to sell.

If the founder can’t sell the product, no one can!

(HARD TRUTH: If you are not getting good sales results, “hiring a sales person” will not solve this. Do more customer discovery to find the authentic demand and/or work on your own sales skills!)

At some point, the founder-as-the-only-sales-person is not scalable. Deals fall through the cracks. The founder is needed elsewhere. You have too many leads for one person.

It’s time to hire your first sales person!

I have seen this transition with many, many companies, spoken to founders, and picked the brains of successful “first” sales people.

It’s a critical time with a lot on the line.

Here are 5 things to know so you’re set up for success as you take the leap from founder-led sales!


1. Expect A Learning Curve

Your first attempt is probably not going to work out.

I know, I know. I said this blog was about setting you up for success.

Here’s the thing — in order to be successful long term, you need to expect some false starts in the short run.

You will read every blog on scaling sales, talk to mentors, get advice from other founders, interview lots of great sales talent, and 90% of the time, you’ll make a change 30 to 90 days later.

IT’S NOT YOUR FAULT.

There is something nuanced about your business, customer, and sales process that no one knows yet!

  • You hire a Business Development Rep (BDR) but your customers hate cold calls.

  • You hire a hungry, scrappy hunter, but you need industry experience.

  • You hire someone with industry experience, but you need a scrappy hunter.

  • You hire a full-cycle sales person but your customers want to self-serve.

  • You hire an SMB sales leader but your product is actually enterprise.

It worked for lots of other companies. But it didn’t work for you.

THE ONLY WAY TO KNOW IS TO TRY.

You test a thoughtful hypothesis and expect the bumps and look for the learnings!

If you’re the founder who makes the right hire for the right process at the right time on the first try?

Buy a lottery ticket, you lucky bastard!


2. Founder is Art; Sales is Science

I’ve heard this from successful first sales reps over and over:

You can’t sell how the founder sells.

The founder is a natural athlete. The first sales person is a student of the game.

Maybe the founder is a sales genius. Maybe they learned to sell along the way.

Regardless, they have the unrepeatable superpower of being The Founder.

They have an intuitive understanding of the customer and problem. They know every nook and cranny of the product. They can tell a heartfelt how-it-came-to-be story.

They probably don’t even know why and how they are good at sales!

The first sales person — the ones who are effective — are avid learners who believe in a sales process.

They soak up the learnings from the founder. Listen to calls, review transcripts, ask about previous deals, shadow whenever they can.

Then turn it into their own sales playbook, often using a framework and process that’s been effective at a previous sales job.

They take the founder’s art and turn it into their science.


3. Your First Rep “Gets” It

A pattern I’ve seen from first sales reps who are successful…

They “get” it.

Your website sucks, the messaging is confusing, your product is barely functional, and this person says, “I totally get it. I see the need. It’s going to be huge. I believe in this.”

Maybe they were a user, from the industry, or they’ve experienced the problem themselves. In some way, they have an inside understanding.

Of course, someone can “get” it and not be successful.

Someone can also have no previous knowledge of the industry and crush it.

(I’ve seen both. See #1 for “Expect A Learning Curve” 😉)

But finding someone with confidence, enthusiasm, and clarity for what you’re building is HUGE.

They bring “Founder Energy” (and customer empathy!) without being the founder.


4. The Founder’s Responsibility

Some of what you’re doing isn’t working.

Yes, you. The founder. Enough stuff is working that overall things are good.

But there’s a slew of wasted time and money.

You just can’t see it.

But the new sales person can.

They will be able to audit the sales process with a fresh perspective.

Are you ready to implement someone else’s suggestions and let go of things that are not working?

Can you let someone else talk to your beloved customers, close your hard-fought deals, and make mistakes along the way?

It’s a tricky balance. You are the expert. Sales are important. A new hire will have a learning curve.

And if they’re f***ing up you need to know quickly.

But no one likes micro management or having reasonable ideas shot down.

Especially not if they’re a really good sales person who is committed to you and the company!

As the founder, make sure you’re ready to loosen the reins, learn how to not be the bottleneck, and for goodness’s sakes, resist the urge to swoop in and shit all over everything.

Avoiding seagull management is key to a smooth sales transition!


5. That Genuine Startup Love

A successful first sales person must want to be at a startup.

Not a make-us-all-billionaires-in-1-year, I-had-a-friend-who-was-at-Facebook startup.

But a real, messy, winding road, no guarantees startup.

Startups mean:

  • Patience — lots of learning, experiments, and ambiguity along the way

  • DIY — sourcing your own leads, making your own slide decks, doing your own demos

  • Financial flexibility — low base salary with high uncapped commissions

  • Long term upside — HUGE financial and career opportunity

  • Great journey — with the right team, the startup ride is amazing. Impact, learning, memories.

If someone asks for a super high base salary and needs a sales engineer to be on demos…they are not your person.

In a few years, they may be a good enterprise rep, but today, they will not be able to hang.

A trend I’ve seen across successful first sales reps — they can play the long game and weather the ups and downs, both emotionally and financially!

Of course, part of the deal is that they are rewarded gloriously for their persistence and patience with compensation and career opportunity.

Your best sales rep should make more than anyone else in the company!

After a 1 year vesting period (protecting the company against hiring missteps), they will have a nice stock option grant too.

For their time grinding it out in the trenches and figuring out a successful non-founder selling motion, they have more than earned it!


Transitioning from founder-led sales is a big change but you WILL figure it out!

Think of the thousands (millions??) of successful startups who have come before you who did it.

Always happy to chat about specific scenarios or discuss at Office Hours or Atlanta Tech Week (happening this week)!!!

What other trends or strategies have you seen with a successful handoff from founder to first sales person??


Special thanks to Kasey Hardin, Brett Lange, and Kathryn Farrell for their insights for this post! 🙏🙏🙏

June 10, 2025
Jun
3
5
min

How To Start Your Founder LinkedIn Journey

7 easy strategies used by top founders on LinkedIn.

Read More

Building your personal brand can be wildly helpful to your company.

In many ways, a founder’s brand is more powerful than their company’s brand.

It can be intimidating at first but with a simple starting plan, you’ll gain momentum and confidence quickly!

I’ve been posting on LinkedIn 2x/wk for several years.

I’ve made great connections, heard from hundreds of founders that appreciate the stories and tips, established credibility as a newcomer, and stayed “in touch” with thousands of people.

It would be impossible to get that reach through events or coffee meetings alone.

I have learned a lot along the way, including from folks WAY BETTER than me like:

If you want to get inspired, see different styles, or take notes on best practices, check out their content!

Shannan Brooks and Evie Lutz are two behind-the-scenes geniuses that have also been hugely influential.

Since LinkedIn is such a popular channel for business folks, it’s a starting place for many founders building a social presence or personal brand.

Here’s what to know about posting on LinkedIn so that you can effectively build your brand.

MOST IMPORTANT STRATEGY: Just get started.

After that, if you’re spending the time anyway, might as well know the tips and tricks.😉

Here are 7 straightforward strategies to maximize your impact on LinkedIn!


P.S. Who’s going to Atlanta Tech Week next week? What events are you going to? Lmk if you’ll be at the Founder Funder Jog or my Startup Summer School sesh on Building a Billion Dollar Business so I can look for you!

Okay, back to LinkedIn!


1. Your Opening Line (aka “The Hook”)

Seth Radman, with 20,000 followers, said he spends 70% of his energy on the first line of a post because it is 10x more important in driving engagement.

It’s called a “hook” and the best ones are usually controversial, surprising, or peak your curiosity!

If a post isn’t performing well, Seth will swap out the opening line. A/B testing in real time.

Go check out the opening lines of top influencers. They are SO good.

One of my favorite examples is “These women are drug dealers.” (Full credit to Lauren Goodell for that one!)

It was a recap of a biotech founders lunch that ended up with 16,000 views. 😉


2. Consistency

It’s better to post 1x/wk for 6 months, than every day for 2 weeks and then go dark.

Why?

  • More sustainable

  • You stay “top-of-mind” with your target audience over time

  • LinkedIn rewards consistency by showing your posts to more people

If you are going all in for maximum followers and views, posting daily is the gold standard.

But this is really hard to do for the long term unless you enjoy it, you have help, or you’re just a total animal (that’s a compliment!).


3. Visuals, Visuals, Visuals

There’s a reason I put cringe-y me-drinking-coffee photos with LinkedIn posts…people love photos and therefore “The Algorithm” does too.

Not ready to see your face all the time? (Trust me, I get it.)

Other non-selfie options include pictures from events, group shots, charts, screenshots, quotes, or other visual digital content.

You don’t have to have an image on every post but including them will usually increase engagement.

BONUS: if you have an image, you can now re-post to Instagram too!


4. Do More (Of What Works)

Here’s the secret from the content pros — have something that performs well?

Do it again!

Not the exact same thing.

  • Use the same opening hook with different content.

  • Do more content on that topic.

  • Recreate that length or style of post.

You’ll notice the best creators do this frequently.

They’re also looking at other people’s content and riffing off their top posts. Nick Maggiulli shares good examples (and a critique) of this strategy.

Piggybacking on a recent trend is another common content strategy. Do your version of the trend or share thoughts on a topic everyone is talking about (tariffs, anyone?).


5. Engage With The Audience

Reply back when someone comments! Comment on other people’s posts!

And for goodness sake’s, keep it positive.

I follow the golden rule:

If you don’t have anything nice to say, don’t say anything at all…because you never know who is a potential customer or employee!

Once you’re a regular LinkedIn-er, it’s common to ask a question or two at the end of a post to encourage engagement and comments.


6. External Links In Comments

You know why people do that annoying thing where they put a blog post link the comments section instead of the actual post?

LinkedIn *hates* external links. It wants as much on-platform content creation as possible.

I read this in their documentation:

You’re blogging on Substack?? Yuck. No thank you. Bring that to LinkedIn and we will reward you generously by showering your posts with views and engagement.

I also saw this weird sign:

DON’T NEVER LEAVE. -Hotel California & LinkedIn Algorithm


7. Algorithm Changes

You know how I said photos and avoiding external links improves performance?

That may not be true forever.

As consumer behavior evolves, so too does the LinkedIn algorithm.

Recently, video performance shot up as LinkedIn added more video features (thus, encouraging video content).

How do you know what the LinkedIn algorithm likes?

  • Track your own performance metrics

  • Periodically review LinkedIn “best practices” via marketing gurus or other influencers

  • Read the code base (Seth Radman, engineering whiz, got insights from this!)


That’s it. Go out there and do it!

You’ll figure it out as you go.

The best way to do LinkedIn is to…do LinkedIn!

Post something today (and tell me) so I can give it a like and a comment!


Do you post regularly on LinkedIn? What advice do you have for those getting started? Any key strategies that I missed? If you want to post more but haven’t, what’s getting in the way??

June 3, 2025
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