Do's and Don'ts of AI Implementation (From an Expert)
I got to pick the brain of an AI expert. Here are the 7 takeaways.
Read More
I got to pick the brain of an AI expert. Here are the 7 takeaways.
Read MoreI got to pick the brain of an AI expert.
And no, it wasn’t Claude. 😂
It was Rebby John, the incredible founder and CEO of Fastlane AI (spoiler alert: Atlanta Ventures Studio company!), who helps mid-size companies understand where and how to get started with AI.
What can startups learn from mid-size companies using AI?
A lot actually!
Here are the top tips from Rebby on what to do (and not do!) to make the most of AI at your company!
Two types of companies:
Know what they want. Need manpower or expertise to execute.
Know they “need AI.” Don’t know what’s possible or where they should start.
Not sure they want or need AI. Literally does not exist anymore. Use or perish! (Note: startups have known this for a while 😉)
Which category do you fall into?
It’s good to get clarity (and be honest with yourself).
Different plan of action for each!
How do you succeed with AI?
Put your best people on it.
Even when they have other things that are really, really important, the successful companies are taking their best people and reallocating them to AI projects.
At a large company, your best people are your busiest.
At a small company, everyone is the best and everyone is busy. 😂
BUT…the idea is that companies using AI successfully are making intentional tradeoffs.
Have no time?
Make time. THIS is the important project.
In Startupland, it means deprioritizing very important things for AI.
Painful in the short term but worth it 10x over long term!
“AI is not good and really annoying” - me, in 2022, after one try with a terrible prompt.
Reminder to all companies — don’t be like me! 😁
Of course it wasn’t good. I expected perfection on the first go round.
The best companies understand that the first implementation is not the final outcome!
One great thing about AI is how quickly you can refine and tweak.
Companies willing and planning to iterate will have the most success!
Startups already know this deeply. 😂
The more you expect to suck the first time the faster you can get better!
2X BETTER: Take current process. Add AI.
100X BETTER: Change the whole workflow!
Companies see most value when they’re willing to reimagine what’s possible.
If you were starting from scratch, what would it look like?
If you had no employees, what would you do?
If you could only use AI, what would be different?
Broaden your perspective to get the most out of AI!
Love this action step from Rebby:
Make a list of pain points, manual tasks, any areas AI might be able to help with.
Then get honest about what AI can and can’t do.
Put your list in an AI tool or ask an AI expert for feedback!
AI is great, wonderful, amazing, but it can’t do everything and some things are going to be faster, easier wins than others.
Better to know that up front so you don’t force it! (Or drive yourself crazy 🤪)
Yes, custom agents are cool. But if there’s a SaaS tool that can already do it, no need for agents.
Opt for simplicity!
I love this decision flow from Rebby and Fastlane AI:
tl;dr: use SaaS → SaaS can’t do it? Use no-code/low-code automation → Low-code can’t do it? Build custom agents.
One of my favorite stories about AI implementation from Rebby was a woman who was not technical, held the same job for 30 years, and she figured out how to automate 75% of her daily tasks using AI!!!!!!!! 🤯
Did she work herself out of a job?
Kind of.
She got promoted!
Fastlane showed her how to use Claude to write Python scripts and she was off to the races.
What used to take 2 hours took 2 minutes.
That’s the ah-ha that makes people believers.
It’s not only engineers or tech-saavy folks.
The most important qualities for AI success?
Willingness to try and openness to learn and iterate!
Give everyone the keys to the AI castle! Build whatever agents you need!
In theory, yes.
In real life, it leads to lots of half-baked agents that aren’t helpful.
Yes, you want everyone to have access to approved and connected Gen AI tools (e.g. Claude or Gemini team account synced with your Google Workspace).
Yes, you want to decentralize identifying agentic AI use cases.
But companies get more value when the responsibility for building AI agents is centralized.
At a mid-size company, it’s a Center of AI Excellence, a hand-picked team that builds, verifies, and rolls out AI agents (and other AI initiatives) to the company.
At a startup of 10+ people, designate a “directly responsible individual” to create agents so your team’s AI implementation is working and aligned.
Yes, everyone is using AI and you want people to be empowered and sharing ideas.
But from the front lines of AI implementations, Rebby sees a truth we all know well:
Ownership and accountability result in higher quality output!
What has worked for your company?? What’s your best AI tip? Do you have a favorite Gen AI tool or use them all?!?
The secrets I shared last week 😉
Read MoreLast week, I had a blast talking to a fantastic group of founders and entrepreneurs at Women + Tech at the Atlanta Tech Village!
The topic?
What founders need to know about raising capital in 2026 — what’s the same, what’s different, and the tactical tips that top founders use.
Here is the FULL SLIDE DECK with a bulleted summary below and some photos!
Not included in the summary:
Say your First Name, Last Name, Title, and sound awesome (our warmup!)
Great audience questions!
Check out what the brilliant and talented Heather Gibbons shared, like, 12 minutes after the event ended:
SUPER AWESOME SUMMARY (that’s definitely better than this one!)
If you’re feeling a little FOMO…
See you at next fun thing!
True in 2006, 2016, 2026
Big markets ($100M in revenue)
Ambitious founders
Resilience
Authenticity → be the best version of yourself! Foundership can look different.
BIG MARKETS!
What’s different (and working) in 2026
AI is disrupting traditional software — but moats still exist!
Straight from David Cummings recent blog which came from Gokul Rajaram on 20VC.
Moats to look for:
Data
Workflow
Regulatory
Distribution
Ecosystem
Network
Physical Infrastructure
Scale
Want to see it in real life? Check out Infinite Giving, Greenzie, Carpool Logistics, and AdPipe!
In-person + physical world businesses with AI efficiencies (Dandy, January)
Robotics (Undaunted)
AI consulting (Fastlane AI)
99% AI businesses (Reframe, Interlock Studios)
Tips and tricks that top founders use
Confidence. Fake it ‘til you make it.
Go to Pitch Practice → pitchpractice.co
WATCH: The real reason female entrepreneurs get less funding (Dana Kanze — TED Talk)
Investor fit — who has $$ that cares about this problem?
Metrics: yours + industry benchmarks. BONUS: look at public companies in their early days
Read the O’Daily 😉 (hehehe. You already completed this one!)
True in 2026 & always
Customers that pay you!!!!!
Design partners
Consulting
Run (paid) experiments
Founder creativity
#sorrynotsorry for all the selfies. I’m basically a professional photographer but I work for free. Stay scrappy, friends.
What questions do you have about raising capital in 2026? What’s working (or not working) for you right now?
Time flies when you’re having fun.
I can’t believe it’s been 5 years since I joined Atlanta Ventures and went from startup COO to early stage investor!
I love reflecting on learnings (and passing them on, of course!!).
Here’s 5 things I’ve learned after half a decade with the awesome crew at Atlanta Ventures.
Settle in, it’s a long game, they said about investing.
That’s 100% true.
And yet this “long game” involved:
The Great Exuberance of 2020 + 2021
The Great Reset of 2022
AI changing literally everything
And, oh yeah, internally at Atlanta Ventures, we purchased 10 city blocks in Downtown Atlanta (total transaction time: <6 weeks) and a massive restoration and revitalization is underway for a vibrant, walkable, entrepreneur-centric city center. 🤯💪🙌
You never know what’s around the corner. True for startups, life, and boring ole venture investors! 😜
I wouldn’t want it any other way.
Not a new lesson, per se, but no one does this better than Atlanta Ventures founder, David Cummings.
Available when you need guidance and sets high level direction.
Builds a team of complementary personalities, backgrounds, and skill sets.
Gives tons of autonomy and freedom. Says yes to almost everything.
I LOVE working in environments like this.
Some people like more structure, tasks, or direction.
But I, and most startup-oriented folks, follow my kindergartner’s mantra: “You don’t need to boss me!”
Wondering if you’re too in-the-weeds or micromanaging? Maybe you’ve heard about this thing called “letting go” but you’re nervous to try it? (You’re not alone.)
Clarify the goals, explain what decisions you do and don’t need to be involved in, then run an experiment to see what happens when you’re less involved.
With the right expectations, direction, and people, your team will love it!
OMG IS IT DELIGHTFUL TO WORK WITH NICE PEOPLE.
Here’s what I mean by “nice”:
Kind, funny, positive
Trustworthy
Responsible
Will communicate a hard thing (to you or someone else) in a clear, thoughtful, respectful way
Differing opinions are good! Ask questions, express ideas, and offer other perspectives without raising voices or making it personal.
Life is too short for jerks.
P.S. Being nice is also good for successful exits. 😉
Should I get better at spreadsheets? Do I need to do complex math in my head? What about golf? Should I learn to golf?
The answer?
“You be you.”
An awesome thing to hear. (Especially from your boss.)
Another way I’ve heard it said:
“Be the best version of yourself.”
Everyone has their own style and strengths.
Yes, always be growing and learning.
But don’t try to be someone you’re not.
It’s hard, weird, and doesn’t work.
Reminder: this is true for founders also!
I’ve seen unicorn founders who are fiery and outspoken. I’ve seen others who are calm and analytical.
There are many forms of excellence.
You be you.
It doesn’t feel like much progress is happening when you’re in it.
Then you look back and realize how far you’ve come!
5 years ago:
The O’Daily didn’t exist and now it has over 225 posts and 1100 subscribers!
My kids were 1 and 3 years old. Now I have 2 kids in elementary school!
We had 2 Studio companies and now we have 7 (including these)!
We’ve deployed over $100M in support of entrepreneurship (much, much more if you include South Downtown).
I was walk-running to get back into shape after pregnancy. Last fall, I hit a lifetime goal of running a Boston-qualifing marathon.
FOUNDERS — what were you doing 5 years ago?!?
I bet you’ve made more progress than you think!
I know folks who hadn’t even started companies yet and now they’re doing millions in revenue!
What does the next 5 years hold?
I have literally no idea.
Check back in April 2031 for an update! 😉
What was your biggest accomplishment over the last 5 years? What lessons have you learned? Any upcoming career or life milestones for you??
Don't hire a COO, says the COO.
Read MoreThe O’Daily is on Spring Break!
But we’ll still clog up your inbox, I mean, offer valuable startup advice!
I’m resharing a post from 2022 on a common founder topic:
Who, what, why, when, how to hire a COO at a startup!
(It’s not what you think…)
NOTE: With the improvements in AI, I would actually update #3 to improving your AI usage vs getting outsourced human help. Things have changed a lot since 2022!
More on AI in the next few weeks! 😉
I frequently talk to founders who are looking for a Chief Operations Officer (COO). These are early stage companies – 5 to 20 employees, $0 to $1,000,000 in revenue, 5 to 50 customers, bootstrapped or small seed funding.
The founder is looking for:
Another leader
Trusted resource who can handle mission critical initiatives
Skills or experience the founder isn’t as strong in (e.g. sales, product/tech)
Someone who can “free up” the mind or calendar of the founder
It’s hard, near impossible, to find an excellent, experienced, affordable startup COO for a company at this stage.
Do not despair! You don’t need to find your magical once-in-a-lifetime unicorn on day one.
Here are 3 strategies to fill a COO role at an early stage startup.
Why buy a sledgehammer when a heavy duty fly swatter does the job? Yes, the very junior folks haven’t worked out. But the range between entry-level ops and COO is vast.
Is there someone smart, hungry, and operationally-minded in your network that could start as an ops manager and grow from there? COOs are hard to find but everyone knows an up-and-coming ass kicker, I mean, operator.
Think: project manager, exec assistant, event planner. Look for a few years of experience in a logistics-heavy role with people or vendor management experience. They will be well-respected, highly recommended, and have moved up quickly. You’ll hear people say, “I trust them to get shit done.”
What area of your business could use a leader or more experience? Don’t hire a general COO. Hire a VP of Sales, Head of Marketing, Finance Manager, or Business Development Lead. Pick someone who thinks about systems, processes, and playbooks.
You’ll acquire deep expertise in an area where you need it today AND the potential to develop a COO from within your organization.
If someone was managing your calendar, paying invoices, following up on client to-dos, designing marketing materials, running your social media, buying groceries, setting meeting agendas, onboarding new hires –OR WHATEVER ELSE YOU NEED– how much time would that give you?
Not sure what could be delegated? Levels CEO Sam Corcos has 56 tasks that are handled by a virtual assistant. Read this amazing Sam Corcos Starter Pack for inspiration.
Is this blasphemy coming from a former startup COO?
Spoiler alert. I was Option #2. I started as the head of Client Success and moved into the COO role after a year. I was motivated, well-prepared, and had deep knowledge of the team and business. The company knew my strengths (and weaknesses - ha!) and moved me into the role with confidence. It was a win-win.
Any other oldie-but-goodie posts I should feature? What are some fave topics? Hope you had a great Spring Break/Easter/Passover/Allergy Season!
(Plus monthly meetups to bookmark!)
Read MoreHellooooo gorgeous weather and yellow pollen everywhere!
Spring in Atlanta has sprung so get out and enjoy some startup events including:
In-person, virtual, and exercise-related 🏃♀️
Education, founder stories, and fun
Conferences galore
Regular monthly events
Add to the comments any events you’re hosting or attending!
3 events I’m attending or presenting at! Come on out. Reply if you’ll be there so I can say hi 👋
📅 Wed, Apr 15, 12–1:30p
📍 Atlanta Tech Village — Buckhead
I love presenting at Women + Tech and YOU KNOW I’ll be bringing the practical fundraising and startup advice.
Meet other great tech women, eat some lunch, ask lots of questions.
I will overshare with behind-the-scenes stories and things I can’t put in writing 😉
Guys are welcome too!
📅 Wed, Apr 15, 9-10a
📍Virtual
Join other healthcare founders, investors, and leaders for small group networking and then hear from these fantastic founders:
A.T. Gimbel and Jacey Cadet are always fantastic hosts. Can’t wait to learn what these founders are building and see you there!
Thanks for reading The O’Daily by Kathryn O’Day! Subscribe for weekly startup advice.
📅 Fri, May 15, 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.
Thank you as always to Katie Begando, Denis Cranstoun, and Julie Pierre for hosting. 🙏
Very friendly, lots of selfie stops and shortcuts, with coffee, water, and sometimes snacks (!) at the end.
These are ongoing events that happen monthly or weekly!
📅 Weekly
📍Atlanta Tech Village - Sylvan + Buckhead
🔗 pitchpractice.co
Led by the brilliant Jacey Cadet, get *FREE* help on your startup pitch!
📅 Monthly, usually the 2nd Thursday
📍Virtual
🔗 atlantaventures.com/events
Join me and fellow Atlanta Ventures partner, A.T. Gimbel, for an informal Q&A sesh on fundraising, product development, early customers, and more!
📅 Weekly
📍Atlanta Tech Village - Sylvan + Buckhead
🔗 atlantatechvillage.com/events/upcoming
Casual, catered lunch with other founders and startup folks. Fridays in Buckhead, first Tuesday of the month in Sylvan. Open to all!
If you’re a member at Atlanta Tech Village, don’t forget about Advisor Office Hours. Chat with startup experts in legal, financial, marketing sales, hiring/HR, engineering, and more.
In-person is BACK and this conference lineup proves it. Just a sampling of what I know about!
Headed to one or many? Follow my world-class advice and make the most of a shoestring budget.
📅 Mon, Apr 20 - Wed, Apr 22
📍Atlanta Tech Village
Get your AI fix. I haven’t been before but if you want MOAR AI, the lineup, topics, and attendees look 💯!
📅 Mon, May 18 - Tue, May 19
📍Charlotte, NC
Fantastic 2-day capital summit in Bank of America Stadium with funding, education, connections, and fun, brought to you by gWen and Innovate Charlotte.
📅 Wed, Jun 24 - Fri, Jun 26
📍Birmingham, AL
Over 1000 attendees and $100,000 in prize money, Sloss.Tech is a fan favorite in one of the hottest tech scenes in the South.
📅 Sun, Aug 9 - Fri, Aug 14
📍Atlanta
It’s a week-long tech party, each day at a different tech hub across Atlanta. Tons of engineering talent comes to town too. Last year, I spoke about building a billion dollar company during the Atlanta Tech Village day.
📅 September 2026 (specific dates TBD)
📍Nashville, TN
Nashville knows how to innovate and roll out the red carpet. A celebration of entrepreneurship with 900+ startups, investors, and ecosystem leaders, it’s a Southern classic.
📅 Wed, Oct 14 - Thu, Oct 15
📍Woodruff Arts Center
Yes, there will be thousands of founders and investors.
Yes, there will be a jog on Wednesday morning. (Check back or follow on LinkedIn for the deets.)
A sampling of fun from a previous year!
I can never capture everything! What are you looking forward to? What did I miss??
Here are some of my favorite event calendars:
Find the most up-to-date event announcements (PLUS PHOTO RECAPS!!) on the socials:
Comment below with events you are hosting or other events you’re attending that we should know about! 👇👇👇
Enjoyed this post? Share with a founder friend!
A founder’s time is valuable.
Best case scenario, fundraising takes 100 conversations and 3-6 months.
I know great founders who had 300 conversations over 12 months before successfully raising. Some do even more never to raise at all.
You’ll hear different philosophies:
It’s a numbers game.
Cast a wide net.
Do a targeted lightning strike.
Go deep with a few.
Take any meeting. You never know where it could lead.
Don’t waste your time if it’s not a fit.
So, should you talk to investors who are not a fit?
How do you balance your precious time with the reality of a sales funnel and the magical startup ingredient — serendipity?
Answer: it depends.
Better answer: let’s walk through scenarios for yes, no, and the nuances so you can decide for yourself!
Always pitch your worst first!
Get some practice. Ask for feedback. Work through the Q&A.
Do this with friendlies who are not a fit for investment.
I’d also do this with non-friendlies (unfriendlies??) before heading to the investors you think are a perfect fit.
You want to bring your A game when you get to those meetings.
You’re not going to play your best basketball on the first day of the season. Save that for March! 😉 🏀
Work that network, baby!
I will take a meeting and be helpful to a founder who is not a fit for our portfolio if I know them well or they came highly recommended from someone I like and trust.
The goal for the founder?
To get feedback and see if I know someone who might be interested.
Will we change our investment thesis because of a personal connection? Nope. But I might be able to intro you to someone who is closer to the right fit!
Also, while rare, if an investor has a long term relationship with a founder (known them for years, involved in previous companies), that’s when they are most likely to “make an exception.”
You don’t fit cleanly into the typical investment boxes of B2B Software or B2B Software. (#momjoke)
No but seriously, maybe you’re medical device-ish selling directly to consumers. Consumer product investors are going to say you’re too medical. Medical device investors will say you’re too consumer.
You will likely have to talk to more investors than someone who is cleanly in one space.
You’re not necessarily pitching everyone for investment.
It’s more of a “I’d love your feedback and if you have suggestions on who to speak with” strategy to grow your network and reach the investor who LOVES the medical device-ish consumer space!
I don’t know how else to explain this but if you feel really drawn to someone, even if you’ve never met them, I’d probably take that meeting.
Maybe your lives have a lot of overlap.
You’re both Amherst College grads who love triathlons and have elementary-aged kids?!?
You’re going to hit it off (with me) right away!
I don’t know if this has ever turned into an investment but making a genuine connection with someone is usually energizing and leads to good things.
“Talk to investors” usually means reach out via email, LinkedIn, a warm intro, and set up a meeting.
That’s very time intensive, especially if that investor is not a fit and highly unlikely to invest.
The math is different if you can go to an in-person event with a lot of investors. Or you meet an investor at an activity that is fun or you were going to do anyway.
(Shameless plug for Founder Funder Jogs!)
Now, don’t go to an all-day robotics event if you are building software for lawyers, but if there’s something that feels like a light lift, you’d have fun, lots of opportunity to run into people and get some face time, that might be worth it.
The investor has told you it’s not a fit. You take the meeting anyway because your awesome at sales and you can sway anyone.
It’s not going to change their mind.
Maybe, MAYBE, this happens .000001% of the time. I’m sure someone has a story but I haven’t seen it and I wouldn’t take those odds.
If an investor has already told you it’s not a fit, they are trying to save you time and heartache.
One less emotional rollercoaster to ride.
Believe them. Use that time on higher ROI activities.
You cast a wide net and sent a canned form letter to an investor who is very far outside your strike zone.
They invest in clean tech software. You’re a consumer dating app.
A brand new entry-level analyst might take the meeting. (A more senior one would not.) Maybe they have metrics they’re trying to hit.
But it’s not going anywhere because it’s not a fit for them and there’s no personal connection or business overlap!
A waste of 30 minutes plus your prep and follow up.
Better to spend time finding a warm or more targeted option.
Things going reaaaaal slow? Like, you talked to 500 people over 12 months with no bites?
It’s tempting to take any meeting you can get. Are you a friend of a friend of a friend of someone who invests? Let’s talk!
Obviously, there’s a balance. You’re going to hear a lot of “nos” and if you’re in a “weird space” (^^in the YES section), it may take more conversations.
But if you’re having trouble fundraising, talking to even more, random investors is probably not the answer.
These are the circumstances when founders get taken advantage of, end up with someone shady or mean, or have a toxic investor relationship that hurts the company’s long term trajectory.
The best use of time?
Pull back and regroup!
Get more customers and traction.
Pivot your market or idea.
Figure out other funding sources like consulting revenue or customer prepays.
Spending a few months focused on the business will be great for your company and usually makes the next fundraising cycle easier.
How do you decide to take an investor meeting? Do you agree with the Yes and No scenarios? Have you seen another strategy work well? Share your tips and advice! 👇
Want more content on fundraising? What questions should I cover? Reply and lmk!
I had the honor of serving as a judge for InVenture Prize last week.
Read MoreI had the honor of serving as a judge for InVenture Prize last week.
InVenture Prize (self-proclaimed “American Idol for Nerds”) is a entrepreneurial competition at Georgia Tech on live TV with $35,000 up for grabs.
Over 72 teams enter the competition with the best 6 in the final televised competition.
THESE STUDENTS ARE AMAZING!!!!!!
(Recap here, full show here, team overviews here!)
Here’s what I was doing in college: planning and attending parties.
Here’s what they’re doing in college: building businesses and competing on live TV to fund their company.
What makes these “kids” special? What are they doing that we can learn from?
Here’s what I saw last Wednesday night.
The longer I’m in this world of entrepreneurship, the more I’ve come to believe that the most important quality of an entrepreneur is…
They really, really want to be an entrepreneur.
You don’t need to be the smartest, the best at sales or (vibe)coding, or have the deepest network.
You DO have to want it so bad that you are willing to do what others are not.
Like I mentioned before, these students are doing different things than many college students (myself included 😜).
They:
spend hours outside of school and extracurriculars on their company
pitch on live TV (with practice, practice, and more practice to get it right!)
talk to everyone and anyone - customers, experts, enterprise companies
pass up fancy internships and big name jobs
care more about their company than their GPA
Simply put — they want it enough to do whatever it takes.
They bring the energy and it’s contagious!
These students brought their A game.
The pitches were as good or better than any I’ve seen.
Did that happen automagically?
No way!
Hours of prep and coaching goes into the 6 minutes we see on stage.
These founders:
showed up for practice sessions
got critiqued by many people
took the advice
practiced
repeated 1-4 over and over
SO many people and organizations are available to support founders.
(Shout out to the many professors, administrators, and mentors at Georgia Tech who gave hours of their time to help entrepreneurial students! 🐝 )
These students did what many do not — utilized (and listened to) the experts available to them!
Think you want to start a company some day?
Do it now!
Don’t get related experience.
Get the actual experience.
Because there’s so much that you can only learn by being the actual, real, full-on founder of a company.
(You’re going to suck at first, might as well get that part over with!)
Regardless of the business outcome, everyone on the stage (reminder: in their teens or early twenties!) has already learned invaluable entrepreneurship lessons that you can only get from doing.
Maybe they learned they didn’t like it 😂
Many of the companies on stage have already iterated their business multiple times based on market feedback.
“Market feedback” is code for: no one liked or bought it, someone else already built it, they got a cease and desist, you know, the startup usual!
Whenever I talk to an amazing young founder, I find out they have been building businesses for years. Did neighborhood errands, jewelry making, lawncare, online selling, or all of the above.
(True for engineers too — many great college-age engineers have been building for 10 years already.)
It takes time and experience to be great.
Every rep — regardless of the outcome — provides invaluable learning.
These students are getting the reps in!
You know who’s using AI?
College kids.
Just like they have always done the cool and innovative things first.
(Facebook — aka social media — started in colleges, I was there 👵)
They are time-rich, asset-poor, and immersed in a high-density social environment which leads to tons of creativity!
AI specifically is amaaaaaazing if you are tight on resources.
One startup was delivering their software for $30/mo!?! It was very niche (software for muralists) but if costs are low, you can go after a niche market that wouldn’t have made sense before!
These students are AI-native and will be building successful businesses faster with fewer humans than ever before.
Today it’s AI. Last decade it was mobile. Before that, Internet.
What’s next? Who knows?
I do know that great founders will be innovating around it.
Because every great founder — young or old — is curious, thinking outside the box, testing the new thing, and looking towards the future!
What trends or lessons have you learned from student entrepreneurs? Did you catch InVenture Prize? What are your fave pitch competitions??
MORE PHOTOS 👇👇
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!
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