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Aug
26
6
min

5 Bad Reasons Founders Raise Money

Should you raise capital for your startup? Here's 5 traps to watch out for!

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Should you raise capital for your startup?

It can be an amazing way to accelerate growth, bring on valuable partners, and increase your chances of building a transformational business.

It can also be easily misunderstood or an ego trap.

Founders think they need to fundraise because “everyone else is” or “that’s how it’s done in tech.”

But if you fundraise for the wrong reason, the raise itself will be time-consuming and frustrating, and it will rarely generate the long term positive outcome you were hoping!

Here are a few phrases or reasons to watch out for!

If you hear yourself (or a founder friend) saying these, take time to reflect on your motivations and goals.

And of course, the O’Daily is nothing if not practical and action-oriented. We’ve included some alternate strategies or ways to think it through instead!


1. “Because my competitors are.”

If all your competitors jumped off a cliff, would you do it??

Seriously though, when the news cycle is reporting that a company similar to yours raised big bucks, it’s hard not to feel like you’ve missed the memo or are falling behind.

Two reminders:
1) Tech news rarely reports the full story.

2) High tide lifts all boats. Aka that competitor is going to invest heavily in marketing for your industry and that will help you also! (Remember: in big markets, there are multiple winners!)

And a story:
This happened to one of our studio companies. Two competitors raised BIG rounds. The studio company raised a much smaller round and stayed focus on serving customers. Fast forward 3 years, those two competitors are shut down or in turmoil. Studio company is winning big deals with hockey stick growth.

It can be hard to take the ego out of it but do what is right for your company!

What To Do Instead:
Analyze your company, product, financial position, and goals. What, if any, is the right amount to raise? Do what’s right for you, regardless of what the other bozos companies in your industry are doing. In a big market with lots of winners, you need to be around long enough to win!


2. “Because it will help us close deals.”

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

And if you can’t close a deal on a shoestring budget, more money won’t help you.

Funding can help fuel sales and marketing.

Adding fuel to the fire is a great reason to raise.

But you need to have something that is already working.

Note: if a customer says that your lack of funding is why they won’t buy your product, they probably weren’t going to buy anyway! As a startup, you can move faster, give better service, and grow with your customers.

What To Do Instead:
Re-read The Mom Test to make sure you’re building something people want. Analyze your sales process. Improve your sales skills. Look at your pipeline — where are people falling out?


3. “Because I need to pay employees…or myself.”

It’s important to pay people. It’s important for you to make money.

But this is like nails on a chalkboard for an investor.

Investors want to fuel growth, not pay salaries.

I recognize that scaling companies involves lots of hiring which involves paying salaries — but paying salaries is not the reason for raising.

Also, some of this is an optics and messaging thing. Remember what investors care about!

It’s reasonable to raise a little bit of money so you can go full time on a business with strong early signs. Something you’ve been working on, have a few paying customers, strong authentic demand, and it could grow into a big ass business.

(FYI — $60-100k salary is a normal range for a founder’s salary of an early stage company, depending on their life stage and number of dependents.)

What To Do Instead:
If your business doesn’t have very compelling early signals (yet) or a path to a venture scale outcome, focus on paid customer discovery options, including bringing on paying clients to fund the business!


4. “Because I want my company to be more valuable”

Raising money can make your company more valuable.

When you can turn $1 of capital into $2 (or more) of growth, raising and investing money into the business adds a ton of value!

Technically, raising money often increases your company’s valuation and you will have more money in the bank (for a while).

But a higher valuation or more money spent does not always translate into a better financial outcome for you or your team.

The valuations change as the economy and stock market fluctuates. The underlying business may have major issues. Or the high capital investment may hurt your chance of getting acquired.

I know companies that are underwater (raised more money than they are worth) or that quietly went to zero, after making headlines as a “success” for many years.

I’m sure you can think of examples too (scroll for tech documentaries on your fave streaming service 😉).

What To Do Instead:
Seek out the “real” stories of founder exits to understand the pros and cons of different paths. Find the quiet successes. People who make a crap ton of money don’t always talk about it 😉


5. “Because I want to be successful”

Raising money is a tool, not the goal.

It’s seductive to think that when you raise, you have made it. All those successful founders raised money and now you will raise and be successful too!

Raising money can definitely accelerate growth and solve certain challenges.

But it also creates new ones: bigger growth targets, key hires to make, better and faster product delivery, more cooks in the kitchen.

Yes, these are “good,” high-class problems that founders are hoping to have one day!

But raising money is not the finish line, it’s just the beginning.

See it and understand it for what it is!

What To Do Instead:
Focus on success metrics other than amount of money raised…

  • Value created for customers

  • Meaningful work and financial impact for employees

  • Meaningful work and financial impact for yourself

  • Meaning and impact created for your community

  • Enjoyment and pride in the journey


It’s easy to make “amount of money raised” the benchmark.

It’s public. It’s in the news. It’s easy to compare against.

It’s like looking at the price of someone’s house.

It gives you a number but doesn’t tell you the full story.

Maybe they are wildly in debt, getting a divorce, and have a casual meth lab in the basement.

Do you want that house? 🙅‍♀️

Stay true to yourself.

Acknowledge social pressure and ego temptation.

Then strategically think about your business and what’s right given where you are — regardless of what anyone else is doing!

Part of being a founder is blazing your own path…even among founders!


What advice do you have for founders considering a raise? What’s a “good” reason and a “bad” reason to raise? Any other ego traps to watch out for??

August 26, 2025
Aug
19
6
min

The Q4 Checklist Every Founder Needs!

5 key items to remember and 4 ways to remember them.

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You can take the COO out of the startup…

But you can’t stop her from making a reminder list and action plan to help startups stay on track to close out the year!

Here are 5 key initiatives to get ahead of as you head into the last few months of the year.

Did you just check the calendar and say, “But, Kathryn, it’s August, what are you talking about???”

Friends, we are 6 weeks away from October.

Which means it’s basically Halloween, which marks the beginning of holiday season where startup dreams go to die, because everyone has 3572 holiday parties to attend, 93 work projects to wrap up, and 56 deals to close…including you!

Here’s the complete checklist of things you’re likely to forget plus 4 action steps (5 minutes or less) to get ahead.

Happy New Year!


The Ultimate Q4 Checklist

1. Pipeline & Internal Deadlines

Decembers deals are sourced today.

If you sell to e-commerce or CPG, they will be in “blackout” (no changes to the website, no new technologies) starting in Oct.

Some businesses do a lot of tech buying at year end. Get on their radar now so you can capture some of their Use-It-Or-Lose-It budget dollars in December!

Regardless of the business, many of your buyers and decision makers will be taking time off. Plus, with the official and unofficial holidays, Q4 is 3 weeks shorter than other quarters (1 week for Thanksgiving, 2 weeks at the end of Dec).

Expect that in the deal cycle and timelines!

Start the urgency now.


2. Conference Planning

Speaking of deals and pipeline, have any conferences on the cal?

(cough, Venture Atlanta, cough)

Here’s your friendly reminder that the early bird gets the best meetings and (if you have a booth) has the best display, swag, and marketing campaigns!

It takes weeks (months) to do a booth design, order swag, ship supplies, coordinate a sales strategy, set up meetings, book air travel and hotels, etc.

Hosting a conference-adjacent event? Book a location and send invites now!

For the most impact, plan your follow up strategy before you leave.

Here’s the full docket of scrappy tips and timelines!


3. Customer Holiday Gifts

If you’re a regular O’Daily reader, you know I give a reminder about Customer Holiday Gifts every year.

✨✨🎁🎁 HERE IS YOUR CUSTOMER GIFTS REMINDER.🎁🎁 ✨✨

As someone who has sent Amazon Digital Gift Cards to customers in January as a “New Years Thank You,” I highly recommend you plan ahead!

Saves money, stress, and makes for a MUCH better customer experience!


4. Company Holiday Party and/or Employee Holiday Gifts

Let’s not forget the team!

I really love these amazing people and want to something special for everyone,” you’ll say on December 20th, when the office is quiet because everyone is out for the holidays.

Restaurants and venues book months ahead for December, so if you’re having an off-site holiday party, jump on it.

(PSA: Hosting a holiday party at someone’s house is scrappy and fun. Hosting a holiday party at your office is lame.)

Ditto if you want to do some amazing holiday swag like custom Yetis or hoodies with everyone’s name.

You can do it in Nov but it will cost 2x more with a rush turnaround and rush shipping.

Here are 10 employee gift and celebration ideas to get you started and 5 *free* ways to show your appreciation anytime of year!


5. 2026 Annual Planning

Sounds insane, but as you can see with all these other things going on, it will sneak up on you!

Here’s the typical timeline:

  • Halloween

  • Thanksgiving

  • Christmas/Winter Holiday Season

  • Frantically Close End Of Year Deals

  • Oh Shit What Is Our Plan And Targets For 2026

  • Everyone Is OOO So I’ll Just Deal With It In Jan

  • Team In Office On Jan 2, Asking What Are We Even Doing This Year?

I’m not saying to start planning now, but plan for planning now. Put a meeting on the calendar for early November to map out the timeline and schedule key dates.

You’ll confirm which methodology to use and incorporate key success strategies!

If you’re big enough to do an annual kickoff at an offsite location, that will need to get booked sooner than you think.


4 Actions To Take Now (5 Min Or Less!)

Are you freaking out?

Maybe you’re just thinking, “That’s nice, Kathryn, but I can barely survive this week, much less plan 3 months away.”

GOOD NEWS!

Here’s 4 simple strategies to stay on top of these items even if you can’t take action today.


1. Decide.

Is this even a strategic priority?

Just because the O’Daily (or anyone else) suggests something doesn’t mean you need to do it.

Reference your Strategic One Page Plan or use this Priority Spreadsheet to see how these initiatives fit in.

Are customer referrals your #1 lead source? Customer gifts might be a GREAT idea.

Do your customers pay you $20/mo?

Don’t spend $ and time on gifts for each of them.

Take a funny team picture and send an e-card.


2. Delegate.

Yes, you need pipeline. Glad you have a VP of Sales who owns that! Check in with them on the plan and forecast.

Does your mom want to plan the holiday party? Great. Forward this email to her and let her pour that “I’m involved because I care” energy into something besides your dating life.

Odds are someone can help with some or all of these items.

Forward this blog to the right person with a note that says, can you handle <#1> and send me the plan by <date>?

(Then Snooze this for that date as a reminder to check in.)

More delegation tips and how to avoid being the bottleneck!


3. Calendar Block.

Add a placeholder on your calendar now.

Even better: schedule a planning meeting with the key stakeholders. Having other people there will give it 10x more accountability.

You don’t have to think about your January conference now. But you do have to think about it in Oct. Put a 2 hour spot on your calendar and don’t let someone schedule over it!

Here’s how I use Calendar Blocks to plan my day and make time for strategic projects.


4. Snooze.

If you literally can’t think about this today, Snooze this email for a day and time when you can revisit.

(One of my favorite ways to stay organized is using my inbox like a to-do list!)

Admittedly, this is the most-likely-to-be-forgotten option, but I love Gmail Snooze.

After a long day, if I can’t take action or decide on an email, I Snooze it. When it pops up again, I handle it in 30 seconds.


Okay, checklist and planning nerds, what did I forget?? What end-of-year item always catches you by surprise? What strategies do you use to stay on top of long term initiatives?

August 19, 2025
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

Read More

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!


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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.

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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
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