5 Things I Wish I Knew Before Becoming a Working Mom
A decade ago, shit got real.
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A decade ago, shit got real.
I was a pregnant startup CEO.
All the startup chaos plus adding a baby? No problem. 😅😳
Fast forward 10 years, I have two adorable boys, a job I love as a tech investor, and a looooottttttt of lessons learned along the way.
Here’s what I wish I knew when I got started…
You may not be able to do everything that you did before. Full stop.
I haven’t done an Ironman since having kids. I’d rather spend time with my kids on the weekend than ride 100 miles. I feel absolutely at peace with that decision.
(Because I still get my fix through marathons which take a fraction of the time! 😉)
I do fewer work happy hours and social things. I don’t read as much business news. I see my friends less often.
That’s okay!
I AM RAISING THE NEXT GENERATION OF HUMANS AND THAT HAS VALUE!!!!!!!
Life changes but it’s okay!
You’ll figure out how to keep what’s most important. And let go of the rest.
Kids force you to focus. Less chitchat at the watercooler, more getting shit done.
You’ll often hear working parents say they got more efficient, more strategic, and cut the fluff (that they didn’t realize was fluff).
Don’t just “do work.”
Be intentional with your time and energy:
What are the most important, highest value activities?
How do I get the most bang for my buck with anything I spend time on?
Examples:
1 small group lunch instead of 5 coffee meetings
1:1 meetings for ideal customers only, no random LinkedIn connections
write a blog instead of emailing 1000 people every week 😉
take photos at events so it’s a social post plus in-person relationship building
exercise while networking (Founder Funder Jogs!)
say no sooner and more often
P.S. You should be thinking strategically about your time and energy anyway but kids make it absolutely necessary. 😜
I’ve said it before, I’ll say it again:
You don’t need announce to the company that you’ll be offline for 15 minutes while you pick your kid up from daycare.
Just do the thing and then get back to it.
I know it’s good to communicate. And some jobs you truly can’t be away, like surgery or rocket launches.
But for most of us, especially working moms, we overshare the minutia of our schedules with disastrous results:
You are available and reply to everything asap unless otherwise stated.
You have no flexibility in your schedule aka an essential component of working parenthood.
You inadvertently create a work prison of your own making!
When I came back to the office after my first baby, I felt like I couldn’t take time away for pumping:
It’s too much time. I’m gone from my desk. Everyone is wondering where I am.
But like most things — I cared and worried a lot more than anyone else did!
The reality is that no one is available all the time because they’re:
on an important call
at a client meeting
attending an offsite ⛳
eating lunch
scrolling social media 😜
So get your stuff done. Do good work. Log on later if you need to reply or finish something. But don’t wear yourself out justifying every minute of your day!
All previous advice assumes that your company is reasonable and modern.
Examples of normal:
Open to flexible scheduling if it’s better to arrive early and leave early.
No problem to take time off for an occasional family vacation.
Work from home if a child is sick.
Support for being the Mystery Reader!
Maybe they aren’t family friendly yet (you’re the first woman on maternity leave, for example…) but leadership is open and listening to feedback.
And then…there’s companies that really do suck. They don’t care. They’re not changing. They want you at your desk 80 hours/week, no exceptions.
REMINDER: It’s your life. You don’t have to work somewhere terrible!
Make a change. Find something else.
Or better yet, create the company you want to work at!!
Usually the person who is least respectful of your boundaries is you.
(Or your children. LOL.)
Boundaries — aka something within your control — can make the difference between loving your job and wanting to quit.
The biggest reason for burnout is having too much to do.
That’s often, at least partially, self-inflicted.
Boundaries are mix of:
getting comfortable saying no
having regular non-negotiables
sticking to a general schedule that works for you (and your family)
My favorite way to handle boundaries is not a big fancy announcement but just casually and consistently make it “your thing.”
(You know how I feel about evening events and getting to bed early! 😉)
These are all real things I’ve heard people say about well-respected, successful founders or executives:
She’s not available until 9a.
He doesn’t have his phone with him during workouts.
He’ll work from the lake house with his family during the summer.
She logs off at 8p.
She’s coaching her kids’ sports then.
He volunteers at his kids’ school every Friday afternoon.
What do those executives say when they’re “enforcing” those boundaries?
They’re using one of these lines!
What do you wish you knew before becoming a working parent? What was the hardest lesson you learned? The most helpful one?
Work on the important things.
I said it last week.
The key to successful founders (and life!).
But — there’s so many distractions!!!!!!
Especially if:
The important thing is going to be hard, take a long time, you don’t know how to do it, or all of the above!
You’re a parent, spouse, pet owner, cool aunt aka have other life responsibilities
You’re like 99% of founders and have ADHD (a fictional stat but directionally accurate)
People ask you questions all day aka constant interruptions
Your creative brain keeps giving you more good ideas
Your office needs to be reorganized (me, anytime I have a hard project)
So how do you actually force yourself to do the hard thing?
Here’s 10 simple ways to create accountability and get-shit-done energy for the things that matter!
P.S. I’m assuming this important thing can’t be delegated and you’re not the bottleneck. But you should double check on that. 😉
One of the most eye-opening and helpful blog posts of all time from John Perry.
If you’re a procrastinator, don’t fight it.
Trick your self and use procrastination to get stuff done!
tl;dr — when you’re avoiding the top priority, you get all the other stuff done. Then when you have a new top priority, you’ll get the previous top priority done.
I do a monthly audit with a few questions that I got from Sahil Bloom.
Recurring invite on the calendar. 15 minutes.
One of the questions is:
What am I actively putting off or dreading?
Sounds crazy but usually just naming the thing makes me realize:
a) Oh wow, that thing has been on my to-do list for 3 weeks and it’s not that hard so I should suck it up and do it and stop being a whiny baby.
OR
b) This isn’t really that important and I’m not going to do it so might as well stop pretending and move on with my life.
Either way, it’s a win!
The ultimate accountability and getting shit done tool.
Setting goals is, of course, a key part of doing important things (even when you’re short on time). Gotta know what the end game is!
Then schedule **a mid-point check-in** ←the MAGIC ✨
Inevitably fires pop up and the day-to-day happens.
People (even founders) lose sight of strategic priorities.
With a pre-scheduled, halfway-point meeting (usually mid-quarter), you have time to course correct and re-focus!
Even if you’re highly motivated and efficient, when your day is 10 minute chunk of “time confetti,” you won’t move the needle on important things.
I LOVE a company policy (you’re the boss) of 1 day/week of no internal meetings.
(Here’s how to have fewer meetings!)
The team has more time for deep work.
YOU have more time for deep work.
Everyone is happier and more productive!
Entrepreneur’s Organization, Braintrust, group fitness, team sports, school, and 100s of other examples.
Create regular time (with friendly, supportive peer pressure) to foster improvement and accountability.
Rule #1 of racing: people run faster times when they have competition to push them.
Make the hard thing easier by joining or creating your own accountability group!
Here’s how to not get important things done: have 12 important things.
(Try this Priority Matrix to actually determine what’s important.)
I personally love and use a 3-item to-do list.
But sometimes even that is overwhelming.
Enter: ONE THING.
Pick one thing. Make it bite-sized even.
Do the one important thing day after day and all the sudden you moved a mountain without realizing it!
I love calendar blocks!
Need to get something important done?
Put it on the dang calendar!
You don’t miss meetings. So treat it like a meeting.
(Now you have to do it but at least you have time!)
Bonus: invite someone else to the calendar invite who will check in or work alongside you.
I use this for workouts, blogs, cleaning the kitchen, writing hard emails.
“I’ll just do 10 minutes.”
Jokes on me though because once I get started, I usually keep going!
Once in a blue moon, I’ll stop after 10 minutes. And it’s great. I’m glad I tried. I fulfilled the goal. I’ll revisit when I have more energy and momentum.
If you’re trying to get something done —OR— looking for a more creative output, you should give yourself more (even fabricated) constraints.
I am loving David Epstein’s new book Inside the Box: How Constraints Make Us Better about how great creativity often comes from limitations not unlimited possibilities.
Give yourself some pressure.
Tell your teammates you’ll do it.
Your name, and only your name. (Two owners of a task or project and no one owns it.)
You might let yourself down, but YOU WON’T DISAPPOINT THE TEAM!!!!
This works especially well if you an Obliger (a la Four Tendencies) aka the ultimate team player and helper.
Share your tips! How do you get ‘er done, especially when the stakes are high and the work is hard?? What strategies or tips work for you?
Every founder is ambitious and competitive.
They have big dreams, good ideas, and high motivation.
So what are the best founders doing differently?
Obviously market and idea selection matters (A LOT).
But even in great markets, how a founder executes day-to-day makes a huge difference in company outcome.
Here’s 5 habits that I see consistently across highly successful founders.
So many shiny objects and competing priorities in a startup.
The best founders are able to tune out the noise and focus on what matters.
Doing the things that only a founder can do.
It varies based on company stage but it almost always involves: selling, funding, strategic planning, and hard conversations.
That’s how the business moves forward.
(Pick your faves)
Procrastination (seriously!)
Say it 12 times. Then say it another 12. Then maybe someone will remember.
Such is the life of a founder.
But the best founders don’t mind.
They will communicate clearly and succinctly the vision, values, and story over and over again.
Until everyone in the company knows it. The new hires do too. Customers. Friends. Friends of customers. Friends of friends of customers.
Why?
Because it’s simple and they’ve heard it 1000 times!
Fine tune a 4 word elevator pitch (start here, you can always make it longer)
You have to take care of yourself to take care of others.
Every parent has seen this first hand. When I’m tired, I’m more likely to yell at my kids or make knee jerk decisions. 😬😬😬
Ditto for founders.
A founder’s mood is contagious. When you’re positive and steady, the team is too.
If you’re freaking out, reactive, and yelling, that quickly permeates across the company.
I also love this coaching concept from Steve Magness:
If the team is down, you’re lifting them up. If the team is hyped, you’re staying grounded.
Either way, you, the founder, have to be in a good headspace and under control to bring what the team needs!
Every great founder is constantly getting better.
Books, executive coaching, peer groups, podcasts — EVERYTHING.
It’s part of their DNA.
It’s also a key strategy for building a successful high growth business.
As Kyle Porter, founder of Salesloft, notably explained:
Last but definitely not least.
This quality is what makes all the other habits possible.
Knowing who you are:
What you like
What you are good at
What you are not good at
What does your company need
How are other people reacting to you
Read the room! Look in the mirror!
You can’t improve, self-regulate, communicate, work on important stuff…without a pretty clear picture of what works (or doesn’t) for you.
Confidence is important.
Got a chip on your shoulder?
Great. No better way to prove everyone else wrong by building a big, successful company. 😉
But you also have to be open, coachable, and willing to work with your strengths and weaknesses.
How you grow the company, who you hire, core values, likely outcomes — all start with clear self-awareness!
What else? What other common habits have you seen from top founders? What has been the most important habit for you? Any tips on how you implemented or improved one of these??
7 lessons (good and bad) I learned the hard way.
Read MoreI’ve said it before, I’ll say it again:
Personal branding is important. Often—gasp—more important than your company brand!
It’s also hard.
Because — despite my very practical suggestions on 5 ways to build your personal brand and how to get started on LinkedIn, both of which are even easier now after the AIpocalypse — I still get a lot of:
How do you do it?
I could never put myself out there!
I know I should but I just can’t press post.
It feels so cringey.
Here’s what I wish I knew before I started.
It’s not analytics or posting strategies.
It’s the personal side of personal branding!
The first time you post, it’s terrifying to hit send.
The second time you post, it’s nerve-wracking.
The 100th time you post, you don’t even think about it. 😂
And I’m not even talking about sharing your deepest thoughts.
Voicing professional opinions, learnings, or memories is still putting yourself out there.
So if it feels vulnerable, that’s okay, it’s normal, and it gets easier!
Because the other important thing is…
The first time you hit publish on something, you’re like, omg I’m going to have 100 trolls and everyone will make fun of me and I’m going to get fired because something I said with good intention is misinterpreted.
But only your 5 closest friends saw the post! Algorithm FTW.
Even when you’re posting regularly and getting some traction, people are still only skimming and thinking about their own lives.
Maybe they jot off a quick comment.
But they don’t notice “their” instead of “there,” your (always) wild bangs, or that you forgot to tag someone.
If they do, they forget one second later!
I was sure the trolls would come for me.
One time they did.
But it wasn’t trolls.
It was…LAWYERS!
(Oh heyyyy nice lawyer friends who read this 👋👋 That was a JOKE! You’ll see where I’m going with this in a minute…)
I wrote this blog about keeping it scrappy on the legal front as a startup. In my LinkedIn post, I wanted to try out a little bit of 🔥🔥🔥 so I opened with:
Look at all that engagement:
But 90% was from lawyers telling me how terrible my advice was! Whomp whomp.
The marketing performance was amazing.
My personal stress levels were not.
It was the first post I ever wrote where people were kinda mean and angrily disagreeing.
I learned important lessons:
I don’t like being controversial.
You have control over how controversial you are.
Never argue with lawyers. 😂
Some people love to shake things up.
It’s powerful and interesting to have a contrarian perspective.
It’s also a great strategy for going viral and getting engagement.
I love that. I respect it. And it’s definitely not me.
But the good news is that I have very few (public? 😂) haters because it’s hard to troll someone who is generally positive.
So take that, haters! (jk jk jk. no controversy here.)
The 100% absolute best thing ever was working with Confetti Social.
I know and adore the founder, Evie Lutz. She “gets” me.
Confetti Social helps with ideas and copywriting for LinkedIn and Instagram based on blogs, photos, and other stories or insights I share.
Content gets scheduled and auto-posted.
I don’t have to decide which photos to use (a 30 minute task when left to my own devices).
I don’t have to agonize over word choice or other silly things that don’t matter because no one cares (See #2).
Having some separation from the go-live of a post helps a ton with speed, objectivity, and worrying about the performance of any single post.
Whether it’s AI, an intern, an agency, or pre-scheduling everything, creating some systems that give you emotional distance can be helpful for any recovering liberal arts grammar nerds perfectionists out there!
Posting content on the internet — ESPECIALLY SELFIES — is cringey.
Agreed.
But now that I’ve:
done it 500x
connected with thousands of great people because of it
realized that I like other people’s photos so they probably like mine
added value to events, companies, and initiatives by sharing photos and stories about them!
I don’t feel cringey. It’s just the norm. Most people appreciate it. And those who don’t aren’t on social anyway!
Luckily, I read this amazing article from Tim Ferris right before I became a global sensation:
11 Reasons To Not Become Famous
It’s easy to chase numbers without realizing what you want.
I am thrilled to have a kind community of folks who care about startups, the Southeast, tech, and wellness!
I want to know and be known by anyone who likes those things.
And since it’s not millions of people (yet), I can safely go to the grocery store without sunglasses and autograph requests.
Whew!
I met a great founder who said:
“I know this sounds weird but I feel like I know you because I follow you on Instagram.”
A dream come true!!
No awkward “So what are you working on?” questions.
Just right into the real stuff because there’s a level of trust and comfort.
We can talk about money, compare notes on startup hiring, and trade kale recipes all within the first five minutes!
The downside, of course, is that sometimes I meet people briefly and forget their name or context.
But they can never forget me!!! (Even when they want to.)
I follow them around the internet with my face in their LinkedIn feed and The O’Daily in their Tuesday inbox.
Sorry in advance and please take pity on this tired mom brain and tell me your name again!
People did tell me this before I started.
(You were correct, Shannan Brooks!)
I knew it on an objective level.
But I didn’t really know.
I talk to people almost every day who will mention the blog, LinkedIn posts, or Founder Jog videos.
Or they’ll say, “I see you all the time in my feed” and then I jokingly but seriously apologize. (Also #sorrynotsorry that’s the algorithm y u clicking if you don’t want selfies and momjokes?!)
Here’s the magic:
It’s a conversation starter.
A connection point.
A way to stay in touch.
Be helpful.
Make “investors” less intimidating.
Share trends or lessons I’m learning.
Answer common questions.
Talk about special events or great founders.
And — most importantly — it makes the hard work of startups and life a little more fun! ✨
Thinking about posting more or building a personal brand? YES! I support you!
Would love to hear any other tips, learnings, or questions in the comments or reply to the email.
I’ll happily share any and all personal brand secrets.
(P.S. Biggest secret is…consistency over time. UGH. Laaaaame. 😉)
2 strategies (plus an email) that work!
Read MoreIt’s a great gig if you can get it.
Be the preferred vendor — fractional CXO, talent partner, outsourced accounting, marketing agency, implementation partner, executive coach — for a VC firm.
Ongoing referral business from well-funded, high growth companies? Yes please!
How do you actually make that happen?
I can’t speak from the consultant side, but I can share what I’ve seen work from the venture firm perspective.
Just like cold outreach strategies that work, it IS possible to break into the referral network of an investment firm.
Here are the two strategies I’ve seen work. (And please share below if you have others!! 👇)
Just like the best warm intro is a founder within the portfolio, the best vendor referral is a happy company.
The simple (but not easy) playbook:
Provide tons of value to a portfolio company
Ask the CEO to send an email recommendation on your behalf
This is the gold standard.
If a vendor or consultant comes to me, I say, help a portco and then I can recommend you to everyone!
This is how I knew that Beata Rouleau and Margaret Weniger were awesome.
Rave reviews from founders I know.
As Pardot grew exponentially, we had trusted partners who would do customer implementations.
How did they become trusted?
Because clients used them for other marketing consulting projects and told us they were great!
The best path to a great long-term partnership of any kind? Help customers!
Until last month, I thought there was only one way in.
I LOVE BEING WRONG!
I shared my “intro from a portco” strategy and a founder told me that he was getting recommended by a PE firm without helping a portco first.
Whaaaaa? 🤯🤯🤯
“How did you get connected to the firm?”
“I worked with one of the partners at my previous company.”
BOOM. Duuuuuuh. Of course!
If you have worked with someone previously, they already know your personality, work quality, and impact.
Fantastic entry point!
It’s what I recommend to anyone first venturing out as a consultant:
Reach out to people you’ve worked with before.
No need for a perfect sales pitch. They know you.
Get some gigs through your contacts.
Now you have experience, happy customers, and a refined value prop!
This strategy applies to raising early capital too!
You might think that the wealthiest person you know (however distant) is the best option for a check, but you’re much more likely to raise from people who know you best.
I know founders who raised from college professors and church pastors.
The power of personal connection and lines over dots!
There are a lot of vendors and consultants that I really like and I’m sure they’d do a great job.
I know them through events, warm intros, or other trusted communities.
But I haven’t seen their work up close.
What if I referred a founder and the consultant did a bad job???
LITERALLY MY WORST NIGHTMARE 😱😱😱
Wasted money and time — because of me????— when startups are already tight on both.
Even if I know someone is great, it may not work out.
But at least I have a clear conscience on the leading indicators of the recommendation (aka I’ve seen their high quality work).
The other calculation I’m doing is time-to-verify.
I could do a deep dive reference check on every vendor —> hours of work.
Or I could read one glowing review email from a founder I trust —> minutes!
Always. 😉
When I was thinking of exceptions, I literally thought of Jane!
I haven’t worked directly with her but she’s built 3 companies and taken at least 2 of them public so, yea, she knows what she’s doing.
Sometimes people’s resume and personality are so good that you’ll recommend them no matter what!
Social media and brand building is an area where someone’s work is public.
Can they do it for your brand? Maybe, maybe not.
But you can see their work in real time so it’s easier to evaluate!
Ditto for outsourced sales, talent agencies, website design, etc.
The more direct experience I have with a job function, the easier it is for me to evaluate someone.
I’m much better at sniffing out Customer Success or COO competence than other roles.
If your service is relevant for the VC firm, you could help the firm as a way to showcase your value.
When Rebby John of Fastlane AI spent an hour talking to us about AI best practices, my mind was blown from the awesomeness.
(Fastlane AI is an Atlanta Ventures Studio Company so it was a different circumstance but I could see how it would work!)
Beware of spending too much time on anything where there’s not a fully paid engagement or deep pain point though…
You might end up with a disengaged or unimpressed VC firm which undermines the whole strategy!
Have you worked with any amazing consultants or vendors? What won you over? What’s your advice for vendors or consultants who want to “break into” startups or investing firms?
It’s always best to get a warm intro.
True for anyone you want to meet and definitely true in the wild world of venture capital.
The gold standard intro is from another founder in the portfolio. (Here’s why.)
After that, any warm intro is great.
(“Warm” intro means mutual acquaintance of some form introduces you.)
If you can’t get a warm intro, do cold outreach.
BUT - for goodness’s sakes - make it thoughtful and personalized!
A.T. Gimbel and I preach this on Office Hours and blog posts.
I can give all sorts of examples of cold outreach that doesn’t work. (I delete dozens of unpersonalized, form emails every day.)
But that’s not as helpful as seeing what DOES WORK!
Here are 4 examples of real cold outreach, why it worked, and what happened next…
Ellen Twomey is one of my favorite startup folks and it came from a simple LinkedIn message…
She said “moving to Atlanta”
She said “founder”
She said “closing the gender gap in tech”
Short
Included email so I could look her up and/or take the convo off LinkedIn
She made an ask but it was low key
I replied.
We had coffee.
Coffee was really fun.
We’ve stayed in touch! Emails, texts, events — we connect every few months and it’s always delightful.
“‘Contact Us’ forms on websites never work…” - says everyone but Paddy McNamara.
Moving to Atlanta + explained why
Specifically mentioned Atlanta Ventures without being totally generic
When we replied, HE FOLLOWED UP!
We chatted.
Then HE FOLLOWED UP AGAIN!
Now, he regularly replies to blogs, shares company updates, reaches out for advice, and proactively stays in touch!
Paddy shared that both of his parents are teachers and he didn’t have connections to tech or business when he started.
What he did works for anyone regardless of their network:
Personalized cold outreach
Follow up in a responsible, appropriate way (not asking for money or aggressively pitching)
Immediately start building a relationship
Stay in touch over the years
The inbox is a black hole. Mostly true. But occasionally an email rises to the top, like this one!
Personalization — clearly has taken time to research and write a thoughtful email
Said the magic words: “Run.” My days are filled with founder meetings. I frequently get asked to grab coffee for career networking. I like these conversations but, unless it’s someone who might be a fit for a current portfolio company, I pass so I have time for founders!
BUT — I like running with friends. So if someone thoughtful and responsible (evidenced by the personalized email) will drive to Decatur at 5:30a for a 6 mile run at 8:30 pace, I am available!
EVERYONE HAS A MAGIC WORD.
The thing you can say that will induce them to open an email, reply, take the next step, make time in a busy schedule.
Examples: Manicure, golf, wine tasting, hair blow out, walk, sauna, heli-skiing, coffee shop near their house, providing dinner for the family, same college or high school, favorite athlete, obscure hobby that you have in common
It will vary depending on the person, but if you figure it out, it’s a huge unlock!
I did a presentation at Atlanta Tech Village. It’s pretty normal for a bunch of folks to say hi afterward.
One woman shared that:
(a) we have the same name (yes, it’s Kathryn Farrell! Kathryns unite!)
(b) my story about Ironmans resonated since she was a D1 runner.
I asked where she ran. University of Florida.
Just so happened that she knew my husband from her college track and field team!?!
It could have ended there but she followed up.
We went running. (See #3 for my magic word.)
She was a reliable and interesting running partner.
She was working in healthcare but wanted to work in tech.
I wanted to get better at running.
Fast forward 3 years, I’m a faster runner and she’s a tech CEO 😉
Saying hi after an event. A great time to make an impression, especially if you are “breaking into” a new industry.
Leveraging charisma. The whole premise of Personality Pool! Especially when resumes (or LinkedIn profiles) don’t capture the full story.
Capitalizing on connection points — same name, sports.
Knowing my husband was an unexpected bonus uncovered via conversation.
FOLLOW UP!!!!!!!
Are you seeing the commonalities?
Personalized outreach.
Follow up.
Focus on human connection.
A little bit of timing and magic in your favor. 😉
Trying to get in touch with someone? Use these tips and keep going!
What is your best cold outreach strategy? What’s worked on you? Anyone that you cold outreached that’s now a friend, customer, or business partner?!? Share the story!
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!
Want to stay up to date? New blogs come out weekly.