From Founder to CEO: How to Make the Shift
Your company is growing!
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Your company is growing! It’s everything you’d hoped for!
It’s time for the big move…
From player to coach.
(Or maybe even from coach to general manager!)
When the company starts to grow, you go from founder to CEO.
You, of course, still are the founder too (lest we trigger another “Founder Mode” debate).
But when long term planning goes from “tomorrow” to “next month” (#startupjoke) or the team grows from 1 to 10 to 100, your leadership role evolves.
This change requires:
Emotional work
Tactical strategies
Let’s walk through it so you’re ready to embrace your CEO era with grace and world domination.
Start here. The emotional work can be harder than any product challenge or sales deal.
This means:
Handing off projects
Being okay with mistakes and a learning curve
Knowing they won’t do it as well as you can…in the short term. But long term it will be better!
Hiring great people
Feeling insecure because you’ve never done it before?
Join the club.
Every successful person feels Imposter Syndrome.
Acknowledge the feelings.
Notice how they manifest (tackling easy tasks instead of important work???).
Then get yourself fired up for the next level.
You figured it out before. You’ll figure it out again.
(P.S. Here’s 4 strategies that top CEOs use.)
Remember — when you started out, you were dying to have this “problem” of how to scale! 😉
You got promoted.
You went from individual contributor to coach. Maybe even general manager.
Coaches can’t throw the winning pitch. General managers don’t even step onto the field.
They win by:
setting the vision
building a system
motivating people
getting the right players
refining their skills
putting those players in the right spot at the right time
The first step in doing a new job is to understand it!
(Not sure what the job is? Use Tactical Items to clarify.👇)
As James Clear says:
Every action is a vote for the type of person you wish to become.
Become the CEO by doing things that CEOs do. Here are specific strategies to uplevel.
Every founder who is serious about getting their company to the next level spends time learning.
You can do it many ways:
CEOs are busy but they find the time to get better and ways to create accountability for themselves.
How do you figure out what the CEO job is?
Work with an executive coach or peer group
Talk to your advisors, mentors, or investors
Ask founders who are a stage or two ahead of you
Successful founders are always getting insight from others with different perspectives or more experience.
The team is looking to you for guidance.
It needs to be consistent and well-communicated.
(Start with a Weekly Update if you’re not doing it already!)
Time to get clear and (over) communicate about:
Goals (← new fave post about goals)
Strategy - via One Page Strategic Plan
Feeling too busy to learn? Don’t have time to work on strategic items?
A simple starting place: conduct a productivity audit!
See what you are doing every week that could be delegated, eliminated, combined, moved to email, adjusted to monthly, or otherwise streamlined.
You get:
More time
Insight about what you (and others) are working on
I have never done this without finding several “ah-ha” moments of things I can cancel, quit, or deprioritize.
Hand off specific tasks.
Clarify when someone can make a decision on their own.
Offer others opportunities to grow.
These are all mission critical to a healthy company and effective CEO leadership.
Here’s my favorite framework and a gentle reminder: don’t be a bottleneck!!
This is not a joke. I mean it.
The best way to get out of the weeds is to be gone for a while and watch how awesome your team does without you!
If you’re not ready for this step, start by not replying.
Seriously.
Let your team know that you’ll be slower replying to emails and chats.
Now, watch with amazement how much people can figure out when you’re not available!
It’s like my kids who can magically tie their own shoes and get their own snacks when I’m not around. CEO MODE!!!!!
How did you develop your leadership skills as your company grew? What was the hardest part for you? Any other tips??
Best of the best. Here's what I forward to founders every week.
Read MoreIn the early days of Pardot, I regularly read two startup blogs:
David was the CEO and co-founder of Pardot. (But that wasn’t the only reason I read his blog, okay??!!!)
The dude was building multiple successful startups and ALSO blogging every single day including weekends.
Also, his posts are like 100 words so if you find my style a tiny bit too verbose, you’re in for a (short) treat!
He still posts every Saturday so if you’re not subscribed, fix that (bottom right corner)!
David’s blog is thousands of posts of startup gems that I still reference regularly.
Want the Cliff Notes AI summary?
Here are the topics and specific posts that I share most often with founders!
Will that partnership unlock millions of revenue for your startup?
Here are the posts I send founders who are excited about a possible partnership.
(Sorry in advance for the buzzkill! 😬 Paul Graham says the same thing in the “Big” section here.)
Read one:
Read more:
If you don’t know the Rule of 40, you should! And here’s your chance to learn.
It’s a great way to answer the question: what’s more important — growth or profitability?
Read one:
Rule of 40 and Startups (Dec 2019)
Read more:
SaaS Valuations as a Rule of 40 Multiple (Jul 2020)
Back to the Rule of 40 for Startups (Jun 2022)
Startup Valuations as Rule of 40 and Market Sentiment Multiples (Jan 2023)
Rule of 40 Growth Multiplier (Feb 2023)
Culture is the only sustainable competitive advantage that’s completely within the entrepreneur’s control. - David Cummings
^^Can confirm! I saw it first hand at Pardot.
Our culture directly impacted our successful outcome. Customers felt it and it created loyalty. It also made us an attractive acquisition target. Exact Target and Salesforce both mentioned it in the acquisition process!
Read one:
12 Ideas To Strengthen Culture (👈 includes links to posts about each idea)
Read more:
Get inspired and see behind the scenes how a legendary entrepreneur thinks about business ideas and tells the stories!
Read one:
Intown Golf Club’s Origin Story (Aug 2024)
Read more:
The Perlant Grand Opening (Jan 2025)
From Historic Neighborhood to Startup District in Downtown Atlanta (Aug 2024)
New Atlanta Tech Village in Downtown Atlanta (Jul 2024)
Salesloft Partnered With Vista Equity (Dec 2021)
How do you find a great business idea?
Listen to the person who is great at coming up with billion dollar business ideas!
For example, David wrote the original post on Authentic Demand which I’ve talked about here, here, and here.
And that’s just the beginning. I share these tips on finding ideas every week!
Read one:
Read more:
If you’re a David Cummings blog reader, what’s your favorite post or topic? Do you have blog posts that you regularly reference or share?
Like I’ve said before, I’m a parenting expert 😂
Read MoreLike I’ve said before, I’m an expert at parenting.
LOLOLOLOL.
Never gets old. #momjoke
Mostly I’m just trying to:
load my kids up with veggies
get them a good night’s sleep
lean on my husband for everything else (thanks, Kyle!!!!!! 😘)
Our kids are 6 and 8 years old, so while they’re not yet using AI agents to start their own companies, we are intentionally introducing some financial and entrepreneurial concepts.
I’ll update this post in 20 years to let you know how we did. 😆
Here are the 5 money lessons we’re teaching our kids, based on what I’ve heard talking to founders, experienced in my own life, and learned from people smarter than me!
The first rule about money is…talk about money!
(Opposite of Fight Club 😉)
Financial literacy starts starts by making it okay and normal to talk about money!
Treat money like a:
tool
resource
topic for learning
Money is NOT:
taboo
secret
only for adults or rich people
I will forever be on my soapbox for founders to lead with money when talking to VCs and for women to be encouraged to talk openly about money (salaries, negotiations, strategies, deal terms).
I think it’s true for kids too.
Some parents want to “protect” kids from the stress of money.
I totally understand that but I’ve also seen it backfire when those kids get into debt or make poor financial choices because of lack of knowledge.
When you discuss money (in an age-appropriate way), you prepare and empower kids!
When our kids started getting Tooth Fairy and birthday money, a big question came up:
How much do you need to save vs. spend?
We held a family meeting to discuss.
We talked about why saving was important:
Saving gives you options.
Decreases stress when emergencies happen.
Enables job flexibility.
Lets you do things like travel and start companies. 😉
Our kids suggested 50% savings rate. Boom! Done.
Now, with any “income,” we transfer half into their bank account and show them on our phone.
The rest is available for them to spend on what they want.
Pokemon cards, golf tees, and activity books of course.
One of the saddest conversations I have is when someone would love to start a company, but their lifestyle is too expensive to make a change.
I’ve known other founders who have given themselves second and third startup lives because their living expenses were low and savings robust.
Of course, you can’t always do this. Maybe you have dependents or you’re paying off student loans.
But keeping lifestyle inflation in check will always serve you.
Save lots and live within your means to give yourself maximum flexibility as a founder and beyond!
Occasionally our kids will want to buy something more expensive or generally “want more money.”
We say: “Great! Let’s talk about how to start a business.”
Ask neighbors about their problems.
Things like:
Taking out the trash
Picking up dog 💩
Yard work
So far, the desire for “more money” has quickly faded when our kids hear they need to talk to an adult. 😂
We have had some successful forays into online selling:
Our kids cleaned the old double stroller and got a % of the online sale.
One child sold toys on Facebook Marketplace to learn about value arbitrage and the circular economy! (That’s what he learned, right? I keep telling myself that. 😉)
I’ve seen the “flyers” made by great founders when they were kids. Hustling from an early age!
Possibly controversial. We don’t pay for chores.
(Here’s our chore system.)
Everyone must pitch in. It’s part of being a family and running a household. It takes work and everyone contributes.
We do this for several reasons:
Parental sanity. Kids can do more than you think and it helps the daily grind when kids do chores! The reminders and debates are annoying. But I like that I’m not doing all the work solo. I’d rather nag them now than later.
Independence and overall life satisfaction. Research shows that doing chores is great for kids’ confidence, resilience, making friends, being healthier, academic performance, and just about everything. So yeah. We’re doing chores.
Learn the joy of a job well done. While great founders love to make money, they also have a great work ethic. Most success comes from giving first, doing the right things, and putting in work without knowing the specific payoff.
Be part of a team and understand collaboration. Every now and then, our kids will get fired up and actually help each other with chores. And even when they’re complaining or bickering (aka most of the time), they are still gonna learn teamwork dammit!
Not a money lesson per se, but very related.
The best founders and most successful people ask for what they want.
If you don’t ask, the answer is always no.
^^one of my favorite blogs of all time. Adam Blitzer shared it with me in the early days of Pardot and it stuck with me 15 years later!
Most things are possible — but you have to ask and you need to ask in a way that make people want to help you.
“THAT’S NO FAIR, I WANT A COOKIE!” is usually not as effective as, “That cookie looks delicious. Would I be able to have one please?”
And you’d be surprised at how many adults still use, “That’s not fair” as a way to ask for something. 😆
Kid Examples:
Our kids order their own food at restaurants
They call their grandparents to ask questions (e.g. can I borrow this book?)
They need to ask when they want to join a playground game, get free sprinkles, or anything else!
How do you get invited to a key event, solicit a customer testimonial, meet the CEO, and generally do things that grow your company and build wealth?
You need to ask.
And how do you get repeat invites, testimonials, and intros?
You need to be really appreciative and grateful so people help you again!
What’s your best money advice? What are you teaching kids about money? If you have adult kids, what worked and what would you do differently? I’d love to hear!
I love sports.
They are a great channel for personal growth, fulfillment, social connection, life lessons, and good ole fashioned FUN!
(Same is true for music and art, but I don’t do those, so someone else is gonna have to write that post. 😂)
I played college softball, club rugby, summer league ultimate frisbee, high school then pick up basketball, before settling into my adult sports of Ironman triathlons and (post-children) marathons.
I met my husband while training for the Ironman World Championships and he worked in pro track and field for a decade before coaching his own clients which includes me as his most difficult favorite.
In other words, we’re into sports and spend (way too much) time analyzing them.
I see parallels across athletics and startups ALL THE TIME!
Elite performance is elite performance whether your venue is a conference room or softball diamond.
Here are 4 key lessons I’ve learned from teammates and coaches that apply to the wild startup arena as well!
The best way to have a terrible race?
Try to keep up with someone who passes you, especially in the first half of the race.
You don’t know their training, plan, how they’re feeling, anything.
They may be only running half the race. They may be way faster than you. They may be going way too hard and will have to walk the rest of the race.
The key to a great race is to stay within yourself, run your race plan, and if you have anything left at the end, let ‘er rip!
When someone would pass me, I used to say, “I’ll catch them later or they were going to beat me anyway.”
At a startup, you can’t let what others are doing (like that super high valuation, big press release, or glamorous social media) dictate your strategy.
Sure, keep an eye on it, but do what’s right for you and your company!
When you’re “mid-race,” it can seem like other startups are raising more or doing better.
But who knows what their P&L actually looks like? They may be weeks away from shutting down. They may have raised too much. They may be quietly imploding.
In which case, you — who has kept an eye on cash and listened to customers — will still be going strong when they are fading away.
How many times have you said…
If I could only run 8 minute miles, then I would be fast.
When I can deadlift 400lbs, then I’ll be strong.
Once I make it to the elite team, then I will feel successful.
Sounds very similar to…
Once we raise money, then it will get easier.
When I make this hire, then I’ll have more time.
As soon as we close this deal, then I can relax.
Guess what?
When you reach this finish line, you’ll realize almost immediately that there is another finish line in the distance.
When you hit 8 minute pace, you won’t go on cruise control.
Because 7 minute pace is now in your sights!!!!!!!
Just like your startup goals.
There’s always another mountain to climb.
It’s always busy. The relaxed week never comes.
You get good at something…and then start on the next improvement.
It never gets easier, you just get faster.
My best memories of Ironmans are not the podiums.
It’s the training days with friends.
Buying $20 of candy to get us over the last climb of our 120 mile ride.
Blasting music at 5:30a during our bleary-eyed bike workouts.
Laughing on the pool wall between sets.
Meeting for a 20 mile long run at 4am to fit into someone’s schedule.
And selfies. Lots and lots of selfies.
Some (most?) of that sucked. But we had fun too.
A great race outcome was important. We wanted it. We cared. But also, we had already won.
Because we loved training.
We were healthy, getting better, learning about ourselves, and making life long friendships.
If you don’t love the process of building a company, if you don’t like the people you’re doing it with…it doesn’t matter how much money is at stake.
When it gets hard, you won’t keep going.
You need to love the work itself — good, bad, ugly — because that’s the real reason we do it.
Regardless of the outcome, we couldn’t imagine doing anything else.
You can’t train for a marathon in a weekend. You can’t build a startup either.
It takes years and years of showing up every day.
Even on days when all you give is 80%.
Math: 80% every day for 3 years is better than 100% every third day or 100% for 3 months.
Startups and sports require hard work. But work over months and years is what matters.
The best future predictor of success is consistency over time.
Warren Buffett is a great investor — who made 99% of his wealth after age 65.
Steve Magness, elite running coach and scientist, tracked improvement factors across collegiate runners. Those who missed the fewest days of practice improved the most.
I saw it in Ironmans. People who spent 1-2 years training rarely achieved their big goals. But those who did Ironmans year after year? They could go from mid-pack to podium.
The best way to succeed in startups? Show up every day, year after year. Layer on improvements and learnings. Figure out how to keep it fun. Keep going when others give up.
Great startups, like most athletic careers, are 10 year overnight successes! 😉
What’s your best sports advice that applies to startups? Anyone training for any races???
More is always better.
…says every ambitious person, especially founders.
I follow this motto too!
Just ask my husband who has to talk me down from overdo-ing it at work, health, running, life. 😜🥴🙃
Spoiler alert: there’s diminishing returns and downsides to “more.”
Today, we’re talking about company valuations but these pros and cons apply to other things as well (ahem, high salaries).
If you don’t understand the downsides and tradeoffs of a decision, you’re not ready to make it!
Your company’s “valuation” is what the market says it’s worth, usually because someone invests money.
Here’s some typical valuation math and how VCs think about investment returns.
These are the two most important valuation formulas that every founder should know!
Most founders want a high valuation when they fundraise for good and obvious reasons.
The higher the valuation the more ownership you, the founder, retains.
If you raise $1M on a $5M post money valuation, that’s 20% dilution.
If you raise $1M on a $10M post money valuation, that’s 10% dilution.
Let’s use the same math as above:
If you raise $1M on a $5M post money valuation, that’s 20% dilution.
If you raise $2M on a $10M post money valuation, that’s 20% dilution — but you get another $1M of investment!
High valuations announce “WE ARE AWESOME” to important people:
Your competitors
Future investors
Current employees
Top talent that you want to recruit
Customers
Your family member who thought law school was a better idea 😉
You’ve been grinding.
You’re years away from an exit, but a high valuation is a milestone.
It’s been worth it.
Someone believes in you and the future!
If your higher valuation means raising more money, that can be helpful.
You can hire more people. You can give yourself a raise.
You don’t have to be the sales person, and marketer, and office manager all at the same time.
You take on new challenges and grow as a leader.
BIG caveat though: with more funding, goals get more aggressive.
So you have more money but you also have more to accomplish.
But we’ll get to that…
Founders often share the downsides of a high valuation quietly and privately, wishing they’d known ahead of time.
Never learn it the hard way when the O’Daily can give you an overview!
Now you can thoughtfully decide for what’s right for you.
If you go out to market with a (too) high valuation, investors may pass even though they really like you and your company.
You may think investors will negotiate and offer a lower valuation.
They might. If the valuation is close.
But often, they will politely and vaguely pass.
They don’t want to burn bridges or offend you by saying your beautiful $10M baby is more like a pretty cute $5M baby.
When impressive founders go out to raise a seed or pre-seed at a high valuation, they often can.
They’re fantastic. Someone will take a chance on their ability for a grand slam.
But what they often overlook is the future math.
In successful startups, valuation doubles every fundraising round.
With a high valuation — especially in the early stages — you need excellent, near-perfect execution to hit the metrics to unlock the next fundraising round.
In seed or pre-seed, you can raise on a vision and great story.
Series A and beyond, you need stellar KPIs (e.g. ARR, CAC, LTV).
There’s little room for sales misses, hiring mistakes, or product pivots.
Which (spoiler alert) are extremely common and normal for early stage companies!
With a fair-but-not-too-high valuation, you give yourself room to run.
If company performance is good but not great, you can raise again under favorable terms, will have more investors at the table, and you keep your employees solvent and happy.
Play it the other way and you have an amazing founder with a great idea who made progress…but has to take a down round or close shop.
It’s heartbreaking.
Companies with great potential, doing good work, helping customers, but hindered by high expectations out of the gate.
A high school star with a strong college career who feels like a failure.
I know multiple founders who have said:
“I’m really glad I didn’t get that high valuation last round because we’d be dead right now. Instead we have outlasted others, we’re hitting our stride, and the team is more fired up than ever.”
A “clean” term sheet means fair and normal terms for the founder without any weird covenants or complicated payback waterfalls.
One thing that can happen with a high valuation is that investors agree but they include “protections” in the term sheet.
“We’ll give you the high valuation you want, but in return, we want to mitigate the risk, so we need to add more contingencies to the deal.”
^^If term sheets could talk.
Run different valuation scenarios through GenAI comparing these terms:
Non-participating preferred
Participating preferred
2x participating preferred
Remember: startup news doesn’t tell the whole story! That big raise announced by your competitor doesn’t mention all the “hair” on the deal.
Know what comes along with the high valuation!
Scrappiness is not always fun but it’s incredibly valuable.
You are forced to:
Listen deeply to customers
Understand exactly what people will pay for
Get creative with marketing campaigns
Test messaging to see what resonates
Use AI to do more with less
Find smart, ambitious talent that punches above their weight class
A risk of a large round is losing your competitive edge.
High valuation → aggressive targets → scale at any cost.
Another variation:
Big raise → big goals → big spending → big miss → big uh-oh.
By the time you realize that it’s not working, you’ve spent millions building or selling the wrong thing.
Can you imagine turning down a purchase offer over a billion dollars?
I know a startup that did.
It wasn’t enough money to provide a good exit given how much they raised.
I worked at several startups who stayed lean, especially compared to competitors.
At the time, we grumbled and worried about having fewer resources:
Smaller team
Fewer marketing dollars
Less product development
BUT we were wildly grateful when large companies started buying businesses in our space!
We had many suitors and some of our well-funded competitors were considered “too expensive.”
So what’s the valuation that’s not too high, not too low, but juuuuust right?
1. Be clear (to yourself) what you’re optimizing for.
Do you want the highest valuation at all cost?
Would you rather have an ideal partner at a lower valuation?
Is exit optionality important to you?
The right valuation for you may be different than another founder.
2. Pay attention to market signals.
You can study the data and analyze the news all you want. But ultimately getting (or not) a term sheet tells you if your valuation is correct.
The market will let you know.
3. Fair and reasonable valuation and terms from a good partner.
Easier said than done but imho THIS is the Goldilocks valuation. Something that both sides are happy with. Fair but room to grow. Aligned on the important stuff. No surprises. A great long term partner.
Not too hot. Not too cold. JUST RIGHT!
Any other pros or cons of a high valuation? What do you think makes a good valuation? What did you optimize for?
AI has *NOT* taken all the jobs 😉
Read MoreAI has taken all the jobs!!!!!
Except at startups where you need humans to run the AI 😉
(AI isn’t taking your job. The person who uses AI is.)
The data shows the job market is tough but the open roles in Startupland tell a different story!
These companies are growing quickly, doing important work, collaborating with other nice, smart people
…AND THEY ARE ALL HIRING!
They’re looking for hungry, motivated, positive, performance-minded folks!
#PROTIP: startups are a great place to get a free MBA while crafting your perfect role.
Share the love (aka this post) with any friends or family looking for their dream job (tips on how to find it) or who want to break into tech (more advice on that).
Of course, post any other open roles in the comments! 👇👇👇
Modern financial management for non-profits. I’m on the board so I can vouch for their awesomeness and growth. 😉 Here’s one of the many reasons why I love this company.
Open Roles:
Thanks for reading The O’Daily by Kathryn O’Day! Subscribe for weekly startup advice.
Automotive logistics platform to deliver vehicles more quickly, safely, and reliably. Raised $12M Series A in 2025 and check out their results from 2025
Open Roles:
…and more!
A private social club for golfers with 6 locations across the country and more on the way! Inc 5000 honoree (plus: #24 in their industry of hospitality and travel).
Open Roles:
**They hire from within so get a foot in the door and grow from there!
The company already has extremely happy customers and 6 figures of revenue. The founder is incredible.
Open Roles:
Proactive robotic security — see the future of security here! One year in and already profitable with raving fans. Here’s their story. Get on! 🚀
Open Roles:
Robotic Engineer
Sales Lead
Reply to this blog or shoot a note to recruiting@getundaunted.com to get more details.
Share with a friend who deserves a dream job!
A great social media agency! I am happy customer. 🙋♀️
Open Roles:
Angel investing made easy. Shared from a friend!
Open Roles:
World’s Greatest Venture Studio filled with brilliant, fun investors who care deeply and help you find a billion dollar idea and scale it. Disclaimer: I may be biased. 😂😜😁
Open Roles:
Founders - we love co-founding companies with passionate entrepreneurs!
Interns - always looking for entrepreneurial-minded students to do hands-on startup and marketing projects (reply to this blog if you’re interested!)
Fave Startup Job Boards:
Georgia FinTech Academy Job Board (over 4,000 jobs posted!)
Most venture firms share open roles at their portfolio companies: Atlanta Ventures, Overline, Valor Ventures
Fave Startup Talent Agencies:
Corps Team (shout out to the G.O.A.T. Jane McCracken! 👋 🙏💪)
Elev8 Hire Solutions (Melissa Davis has been helping startups for decades!)
Is your company hiring?? Share any great roles or companies below!
You’ve read The Mom Test!
You’re hunting for Authentic Demand!
You’re looking for those first paying users!
But how do you get people to pay you money when you need money to build the thing that people will pay you for?
A chicken and egg problem…THAT WE’RE GOING TO DEBUNK TODAY!
Here are 5 ways I’ve seen real startups prove demand and pre-sell their product before it existed!
Are these the exact strategies you should use?
Probably not.
Every business is different.
But hopefully it will trigger an idea, inspire you, or give you a starting place for your own version of a pre-sell!
We used this playbook in our Venture Studio when launching The Perlant and Intown Golf Club.
We sold club memberships before the club existed.
Explain the vision. Get people excited. Offer a founding membership for $1000.
When you have 100 future members, who want it enough to put money down, several amazing things happen:
you know you’re onto something real
$100,000 of working capital
100 evangelists (aka unpaid sales people) who recruit their friends
strong data points to share with potential investors
What’s the “selling memberships” version of what you’re working on??
No tech? No problem!
Deliver the solution manually but make it much, much easier than what they are doing now.
(And automate the tech over time once you have paying customers and you know exactly what will solve their problem!)
I’ve seen this work for real companies like:
a logistics marketplace — got to 6 figures of revenue with a spreadsheet backend
remote monitoring services — leveraged offshore resources while developing scalable tech
task management tool — software frontend with humans behind the scenes
Customers are happy to pay because their experience is so much better. They don’t care how it happens!
What is the 10x better experience you are selling? What can you deliver now, knowing that you’ll improve and automate over time?
Thanks for reading The O’Daily by Kathryn O’Day! Subscribe for weekly startup advice.
I have always loved this example from The Rebel Business School, who I also mention here.
They don’t build the content for any of their entrepreneurship education courses until they have sold the course!
They use a syllabus overview in the sales meeting. If they win the deal (they sell to economic development organizations), then they hustle to build out the specific course materials.
You can also do this for:
New modules on your platform — get customer contracts first
Next locations — do sales outreach or inbound sign ups to see where demand is
Your whole product — they’re called design partners! And it’s more possible to code a product in a few days than ever before!
P.S. Large companies do this too. They sell dreams, I mean, showcase aspirational customer use cases at their premier events, then spend the rest of the year actually building them!
What do you actually need to sell? Can it be a mock up instead of a full product? What’s the minimum viable version (that you can later deliver on) to get a customer onboard?
Marketplace Building 101.
I love love love the Lenny’s Newsletter series on marketplaces! It tells the real stories of how great marketplaces got started.
Spoiler: it’s messy.
The company’s value prop is something like:
“We have many Things (babysitters, errand runners, hotel rooms)!”
Then someone buys a Thing from the marketplace, except it was a placeholder/test/fake-it-til-you-make-it listing.
They scramble behind the scenes to locate and deliver the Thing quickly so it feels easy and seamless.
And this is how marketplaces get started!
Lots of faking supply or demand until awareness grows and you don’t need to fake it anymore!
People also do this with consumer products. Offer a pre-order option or explain that it’s a 2 week turnaround.
Do you think Etsy creators are holding warehouses of inventory (beyond their guest room and garage 😆)? No way!
What can you sell now and then procure after? Especially great for services or physical products!
I love consulting and community-building as a way to get customers! This is combo of both.
Your insights and expertise are the hook. Your research becomes a coveted and helpful data set.
You can “pre-sell” things like:
Paid newsletter
1:1 consultation
Small group events
Workshops (in person or online)
You build trust as the expert, deliver value to your target customers, while also generating revenue and getting insight for a tech product!
Can you monetize your expertise now so that it funds (and shapes) your long term tech vision?
People can build tech tools faster than ever. Like, hours instead of weeks and months.
Are these pre-sell strategies old fashioned now?? Why not just build in 30 seconds and then regular-sell?!?
The best founders I know are using AI and these strategies. They can iterate faster and better with AI. They can run even MORE experiments, MORE quickly.
You still have to use your own judgement and brain. Yep. You may also have to talk to real humans to learn from them and sell things. I know, terrible really. 😉 Exclusive AI-Agent-to-AI-Agent communication isn’t here…yet!
When everyone can build more products faster than ever before, you will need to separate yourself from the noise! Selling before you build will be a differentiator. Your solution will be better; you will be closer to your customers.
If you can build an amazing product super fast that people will pay for right away, amazing! Keep going! It’s very hard but if you’ve done it, congrats (and tell me about your product)!
Have you pre-sold your product before? What worked for you? Any other pre-selling lessons — good or bad — to share??
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9+ Events You Don't Want To Miss This Spring 2026
Read MoreWas one of these a New Year’s Resolution?
Do more networking
Get better at sales
Start running again
Raise money for your startup
Build relationships with investors
IT’S YOUR LUCKY YEAR!!
These upcoming events will accomplish some or all of your goals!
What else should we know about?? Add to the comments any events you’re hosting or attending!
📅 Wed, Feb 4, 8:30-10a
📍Atlanta Tech Village - Buckhead
Join other healthcare founders, investors, and leaders for networking and alll the startup lessons and advice from Chris Spears, founder and CEO of OrderlyMeds.
📅 Tue, Feb 25, 4–6p
📍 Atlanta Tech Village — Buckhead
Join Atlanta Tech Village’s Women + Tech Program and the Women’s Entrepreneurship Initiative for a panel of women investors and operators (including yours truly 🙋♀️) sharing real insights on accessing capital, scaling responsibly, and navigating growth.
It’s an honor to be part of this all-star lineup:
Jennifer Bonnett – VP of Technology & Entrepreneurship, Invest Atlanta
Jewel Burks Solomon – Managing Partner, Collab Capital
Stefanie Diaz – Principal of Innovation & Venture Strategy, Catalyst by Wellstar
Alaina Percival – Venture Partner, Valor Ventures (Founder, Women Who Code)
Register here.
📅 Fri, Feb 20 - Sun, Feb 22
📍 South Downtown
Is this the coolest weekend ever? Urban innovation + World Cup + Atlanta’s Downtown. Let’s GOOOOOO! (Read more here.)
A 48 hour civic build moment for students, entrepreneurs, technologists, creatives, civic leaders, and neighbors to collaborate on ideas and innovations around:
Public Safety & Walkability
Cultural Preservation & Storytelling
Economic Opportunity & Business Vitality
Sustainability & Public Space Activation
Civic Engagement & Advocacy
You will directly impact what happens in Downtown Atlanta for the World Cup and generations to come!
📅 Fri, Mar 6, 11:30a-12:15p
📍 Emory University
This is one of many excellent sessions during the Executive Women of Goizueta Annual Leadership Conference including keynotes from Paige Alexander, CEO of The Carter Center, and Sara Wechter, Chief Human Resources Officer at Citi.
I’ll be on this panel alongside:
Chi Chi Okezie, Owner/Producer of SIMPLEnetworking, LLC
Clair Flores, CEO of OODAZU
Meredith Swartz, Chief Planning Officer of Mercy Care
We’ll be sharing our professional stories plus advice for folks navigating pivots, promotions, or visibility moves.
You KNOW I’ll be talking about:
how to establish credibility with anyone (even if you feel young or inexperienced!)
And whatever else these smart women want to dig in on!
Thanks for reading The O’Daily by Kathryn O’Day! Subscribe for weekly startup advice.
📅 Wed, Mar 11
📺 GPB Live Stream
📍 Ferst Theater, Georgia Tech Campus
One of my favorite events of the year — this is the ultimate Shark Tank-style event with $30,000 of prize money going to the top Georgia Tech entrepreneurs!
See it live on campus or watch from home on GPB streaming.
I was a judge last year and didn’t swear on live TV so I got invited back! 😅 Let’s see if I can keep a lock on the f-bombs for another year…while also (and more importantly) getting to know the next generation’s top founders!
These “kids” are SO impressive. Prepare to have your mind blown! 🤯🤯🤯
📅 Fri, Mar 13, 6:45a
📍Tech Square - Biltmore Ballrooms
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.
Keep up your running resolution alive (and it counts as “work”)!
📅 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.
📅 Thu, Feb 12, 12p
📅 Thu, Mar 12, 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.
📅 Mon, May 18 - Tue, May 19
📍Charlotte, NC
Snag your tickets now for this 2-day capital summit in one of my favorite Southeastern startup cities, put on by gWen and Innovate Charlotte, hosted in Bank of America Stadium!
📅 June
📍Atlanta
Dates are not yet released but if you’re thinking about coming to Atlanta in June, YOU SHOULD!
This week is a tech party with great events across tech hubs and tons of engineering talent converging on Atlanta.
The last two years I’ve talked about building a billion dollar company at the Atlanta Tech Village so I’m ready with fresh jokes and lots of advice. 😉
I can never capture all the awesomeness. What are you looking forward to? What did I miss??
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.
Comment below with events you are hosting or other events you’re attending that we should know about! 👇👇👇
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Top 4 strategies (including fave tools) from a startup CRO and AI expert.
Read MoreIf I had a nickel for every time someone asked me…
How are other startups using AI?
What’s the best way to get started with AI?
How can I use AI to sell more?
…I would be a billion dollar company! (#momjoke)
Last week, I had the pleasure of sitting down with the kind and brilliant Beata Rouleau, fractional CRO and startup AI expert, who gets rave reviews from founders I trust, to get her take on these burning questions.
She’s on the front lines, improving Go-To-Market processes for startups — using AI of course.
Now you get her best advice right here on the O’Daily!
For more of Beata’s helpful insights (and access to her workshops), follow her on LinkedIn and subscribe on Substack.
Do you have your notepad AI notetaker ready?
Here’s Beata’s #1 piece of advice, available for use in the next 5 minutes.
Use the CRIT framework: a prompting method to transform AI from a glorified search engine into a strategic thought partner.
This simple framework is magic…
Context
Role
Interview (This is the secret sauce)
Task
It’s easy, repeatable, vendor-agnostic, and works for almost any AI need you can think of!
Give the background information.
Examples: include your situation, goals, challenges, audience, and constraints. The more context you give the better the output!
Tell AI who to be. Assigning a specific expertise focuses the response and shapes the tone.
Examples: strategic advisor, copywriter, investor, researcher, brainstorm partner
Before AI produces anything, have it ask you clarifying questions - one at a time. This is what separates CRIT from other frameworks.
Here’s the prompt: “Interview me asking me 1 question at a time, up to 5 questions, to gain additional context.”
^^ this is key!! Gives you and AI more clarity by forcing you to slow down and think. AI learns what actually matters; you surface insights you didn’t know you needed to articulate.
Explain the output you are looking for. Be specific about format, length, and what success looks like.
Examples: Come up with 5 non-obvious strategies to solve this problem, draft 3 email templates, create a 10 slide pitch deck
Boom! You are the thought leader, AI is a thought partner.
No more wondering where to start or asking why your AI doesn’t “get” you.
Share this prompt with your team, your friends, even (gasp) your parents!
You’re gonna love this.
Beata recommends Glyphic as your AI sales copilot.
A Gong-disruptor at a fraction of the price. Yes, please!
(Not there yet? Otter.ai is great for audio recording and transcripts. Fathom has good video recording if you are more presentation and screenshare heavy.)
Once you have call recording data, you can start doing cool things with AI agents.
Don’t be scared of AI agents!
As Beata explains, agents are just “triggers and specific asks.” When X happens, do Y. That’s it. Totally manageable! 😅
Glyphic lets you build these directly in the platform.
Follow-up Email Generator: based on specifics in the call transcript, auto-generate a customized follow up email that references what was actually discussed. No more generic templates!
Competitor Analysis: run a monthly analysis of sales calls to understand what prospects are saying about competitors (good and bad). Use that insight to fine tune your objection handling or run a targeted outreach campaign to users of that product.
Trending Topics: similar to your competitive analysis, what are customers talking about or asking questions on? Pull out the trending topics to plan your next marketing campaign, LinkedIn posts, or webinar.
Deal Stage Patterns: look at transcripts of closed won deals, closed lost deals, and calls that moved forward but stalled. What patterns emerge? For example, if most closed lost deals are not the right fit, can you use an AI agent to better qualify leads before a demo?
Call Scorecards: using BANT, MEDDIC, or other sales framework, you can assess a sales rep’s calls and overall sales process. Any common misses? Use AI to create training materials around that topic. 😉
As Beata wisely points out, at a startup, every lead matters.
Once you have them on the phone, er, Zoom — make the most of it!
Not an AI recommendation per say but since I get asked about CRMs at least 5x/wk, I know it’s top of mind!
Beata says Hubspot continues to be the go-to startup CRM and is her recommendation for most startups.
(Kathryn’s note: can confirm - most of our portfolio companies use Hubspot!)
It is simple to set up with good out-of-the-box functionality but robust enough to have many integrations (including Glyphic) and customizations.
Salesforce — while obviously still the greatest company on earth since I worked there post-Pardot acquisition — is too complex and expensive for what most startups need unless they are enterprise or highly niche.
Most founders start with a spreadsheet (love this, stay scrappy).
Then they agonize over which CRM to use, often starting with a smaller, lower-cost option, which — if things go well — they’ll outgrow in a year.
Then they painfully switch to Hubspot and berate themselves for not starting with Hubspot in the first place.
To which I say, you had very few customers before and even less money so it was probably a good decision. Growing pains are high class problems!
#PROTIP: If you’re thinking about Hubspot, make sure you get yerself a deal!!
Hubspot offers major discounts — to the tune of 90% — through partners like startup hubs (ahem, Atlanta Tech Village), accelerators, VC firms, or sometimes credit cards like Ramp or Brex.
It will be very inexpensive to start and then get annoyingly expensive when you’re further along.
Beata has been hearing good things about GoHighLevel but needs to dig in further. She can neither confirm nor deny if it’s the next Hubspot or another low cost CRM that you’ll painfully outgrow in a year. Stay tuned! 😉
AI not doing what you want?
Before you swear off all technology and rage post about the overhyped AI bubble, Beata recommends:
Take a pause.
Reset.
SLOW DOWN.
Mostly likely you were going too fast and didn’t give enough information.
Whatever do you mean, Kathryn asks, as her 1 line prompt didn’t result in a perfect email draft?? 😜
Here’s the secret:
Give clear instructions.
Getting AI to work for you requires the same skills that make a great team manager:
Can you explain what you actually want?
How specific are you with deliverables?
Did you provide enough context?
Back in the day (when I was walking to school in the snow uphill both ways), great managers managed people.
Today, your team probably has more AI agents than humans.
Not only are they more cost-effective and don’t expect donuts on their birthday, but they don’t care about your demanding tone, snarky comments, and unreasonable asks like a 20 page report in 30 seconds!
Regardless of whether you’re managing people or AI agents, clear communication and more effort on the front end will save you time and frustration overall.
Is AI the answer to all of our startup problems? Of course not!
As Beata reminds us — we still need to work the muscle of our brain!
AI + human creativity is where the magic happens.
AI is your thought partner, assistant, researcher, sounding board, and force multiplier.
YOU are still the thought leader!
How is your startup using AI? What’s your best AI tip? Favorite tool?
P.S. Want more Beata? (I know I do!) Go say hi on LinkedIn and subscribe to her Substack!
Simple, straightforward ways to build alignment
Read MoreNew year, new ideas!
…And new pushback from the team. Whomp whomp 🙃
It’s normal and healthy to have internal debate at companies.
You want to have at least a few skeptics on the team so help you think through downsides and clarify your approach.
But when it’s important to get alignment around a new initiative, what can you do?
Here are 2 very simple but effective ways to get your team, board, family, anyone on board with something that feels like a (scary 😱) change!
I LOVE this strategy and do it all the time in my own life, personally and professionally.
Almost any new idea or project, I consider an experiment.
Let’s try it for a predetermined time frame and then reevaluate.
Takes the pressure off everyone involved!
Keeps the door open for change or feedback
Allows you to get started without having to consider every possible repercussion
Breaks it into a manageable chunk of time (e.g. it’s not forever, just for a month)
Makes it easier for people to come along on the journey
(Literally for everything but here’s some examples…)
Trying a new wellness habit
Seeing if an event has good marketing ROI
Implementing a new metrics tracking system
Working with a consultant or coach
Iterating on your family’s nighttime routine
Launching a new product offering
Going after a stretch goal like speaking at a large event
All of these examples have money, time, or ego at stake. Lessen the risk by making it an experiment!
#PROTIP
Schedule time at the outset for the evaluation and feedback stage. Make sure to *ACTUALLY* cut or pivot the experiment if it’s not working!
Another strategy I love across all areas of life is bringing people into the fold by asking for their help.
According to the Ben Franklin effect, you like someone better after you’ve helped them, even more than if they helped you.
(This is why asking for feedback from an investor is a great way to build a relationship!)
Start with that person’s strengths (“You are great at designing a streamlined process.”)
Acknowledge concerns or reluctance (“I know you are not sure about this new product release strategy.”)
Ask for help (“Would you be able to spend a few minutes mapping out a process that might work?”)
Explain their importance (“Your operational brain power on this will really help the team save time and be more efficient.”)
Something specific they are good at
Feedback on a v.1 or something that already exists (this can take less time if bandwidth is a concern)
Plan or recommendations on how to best implement a high level goal (“Here’s the desired outcome — how do we get there?”)
Finding the right person or training someone (“Can you help me find and onboard the leader we need?”)
A good attitude (“Your energy is contagious.”)
If you’re asking for their time and work, specify how much time they need to spend (“30 minutes to help me think through pitfalls and how to avoid them”)
If they have only criticisms, ask for their suggestions and solutions! (“What would you do? How would you mitigate that?”)
What *NOT* to do
Ask for help and then totally ignore it 🥴🙃😬
What to do instead
Explain upfront how you will use their help and the decision process. Don’t promise to include someone’s ideas. (“I’m asking for everyone’s input and then will use that to make a final plan.”)
Give public shoutouts for any ideas or work they did (“Sarah found a great software option for us.”)
Find something to include — give everyone a small win within the final plan (like in the Core Values process). Even if you don’t have high confidence or disagree about that item, if it’s not mission-critical, it may be worth conceding for the sake of alignment and the larger goal. Again, you’re testing it out and will reevaluate!
#PROTIP
Works for families, kids, loved ones as well. If I do a small part of a house project, I feel more ownership and interest in future projects. When my kids help cook dinner, they’re more likely to eat it. We let everyone pick an activity for family trips — adults have the final say — but everyone shapes the plan!
How do you get your team onboard? What helps you navigate change? Any tips or strategies to share?
Want to stay up to date? New blogs come out weekly.