8 Interviewing Mistakes (That Even GREAT Startups Make)!
And how to fix them, of course!
Read More
There’s no high school or college classes on “How To Run an Efficient and Productive Hiring Process If You Decide To Start A Company” so how are we supposed to learn this stuff??
Trial and error, baby! 🙃
Most founders — especially if the company is doing well — are thrown into the hiring fire.
And the more you’re hiring, the more little things add up, positively or negatively.
All of these mistakes are things that I did, sometimes for years, before someone showed me a better way!
For the sake of your team and all your future employees…
Here are 8 common mistakes — and how to fix them!! — that good startups make when hiring.
The first meeting?
15 minute Zoom call.
Do not — I repeat, DO NOT — do an in-person 30 minute meeting.
A 15 minute Zoom call will tell you a lot:
Can they use technology?
Can they show up on time?
Do they have normal social skills?
Are they nice, funny, and generally competent?
Does their resume check out?
Block off a few hours per week for 15 minute intro calls and have candidates schedule via Calendly link or other DIY scheduler.
Hear that echo? That’s the sound of your calendar having more open space!
Exception: a personal intro to someone highly recommended may warrant a 30 minute coffee meeting or Zoom to start out.
BONUS TIME SAVER: Add a video component for entry level roles where high EQ matters and previous work experience may not capture the full picture (e.g. BDR or customer support). Candidates record a 1 minute video to supplement their resume. You can set this up in most Applicant Tracking Systems!
This ever happen to you?
Gather in a room to discuss a candidate.
Realize that we all asked similar questions.
No one asked the questions we really needed answered.
Me too! 🙋♀️
Two things to prevent it:
1) Make a quick plan before you start interviewing for a role.
Who is going to meet them?
What order are we going in?
Who is assessing which role requirements (e.g. sales skills, core values fit)?
2) Relay “open questions” to the next person in the process.
As you meet people, you’ll have things you’re not sure about. You need to let the next interviewers know so they can dig in on those!
You don’t want to get to the end of a multi-hour interview and no one has followed up on that possible yellow flag.
There’s 2 good types of questions:
What have you actually done? (Tell us specifics of past experience.)
Here’s a specific situation. Tell us what steps you would take. (See how they think through problems.)
Bad questions:
Hypotheticals (“How would you help our customers?”)
Self assessments (“What are your strengths?”)
The “bad” questions basically evaluate how good someone is at talking about themselves and sounding smart.
Which isn’t totally irrelevant in business 😂
But probably not the main skill set you want on your team.
Better questions = better insight into candidates = better hiring!
Another question-asking mistake that well-intentioned folks make. Myself especially!
I thought that having an arsenal of questions to ask showed the breadth of my interview skills.
FALSE.
Ask the same questions to all the candidates!
Easier for you.
More fair to them.
Then you’re comparing apples-to-apples rather than apples-to-favorite-roller-coaster-rides. (Or whatever creative question you came up with 😜)
When a candidate passes the 15 minute Zoom screening, time to meet in person!
YES: Have a “waterfall” plan of who will meet the candidate next if you like them. NO: Put a 2 hour block on the candidate’s calendar.
For the candidate, schedule a 30 minute meeting with 1 or 2 people.
You can say something like, “Interviews are usually 30 minutes, sometimes they’ll run a little longer depending on who is available to chat.”
Then you can put a hold on people’s calendar internally. The next folks in line will meet the candidate if the first meeting goes well.
If the first interviewer decides the candidate is not the right fit, no one else has to meet them.
(I’m happy to share exact wording and logistics. Usually after a few times through, folks will get a hang of the handoffs, language, and flow, especially if it’s the same interview team — see “Not Having An Interview Plan” — but you know I’ll give more detail if you want!)
This means you spend 30 minutes of 1 person’s time instead of 30 minutes of 4 people’s time.
AND it’s a better experience for the candidate.
Nothing feels worse than being sent home after 20 minutes when you had a 2 hour interview scheduled.
That person may have taken time off work, gotten a sitter, played calendar gymnastics for that 2 hours.
It’s unkind to them and also hurts your company’s reputation because they’ll have a negative experience.
Way more fun to have a 30 minute interview turn into multiple meetings!
If they don’t have time for more meetings today? No problem. When there’s interest on both sides, things move quickly!
Having a hard time assessing candidates for a role?
Maybe you’re only talking to them rather than seeing the quality of their work!
A few ideas on how to see their true work product and abilities:
They submit examples of previous, related work and you review it with them. You want to understand their process, strategy, lessons learned, and impact (and of course that they actually did the work 😳).
Do-at-home exercise that relates to the work they’d be doing in the job. This is after the in-person interviews go well and they are close to a job offer. They should be able to do it within an hour or two with resources generally available (e.g. your online Knowledge Base). You’re not looking for perfection, you’re looking at the quality of their thinking, communication, effort, follow through, research, and generally, could they do the job really well?
At-home work examples:
coding exercise
building a AI agent
make a prospecting list
marketing analysis of the website.
handling customer issues
White boarding session to work through a current company problem. This is especially great for executives/team leaders who deploy resources and execute long term plans, operations roles, engineers, probably other uses cases too!
How do they think?
What questions do they ask?
How to they work with others?
How are they on the fly?
A paid short-term engagement that is real work you need done. The key is — pay them for their time if it’s going to more than an hour or two of work.
Or whatever makes sense for the role and your company within reason.
You want the candidate to say, “I’m glad I tried,” not, “What a huge waste of time, I can’t believe they had me do all that for nothing.”
So yeah, keep it reasonable, you crazy founders! 😉
Every candidate is a future advocate for your brand!
At Pardot, the highest compliment was someone who didn’t get hired referring a friend.
There’s two parts to a good interview experience:
the people they meet & how those people act
the communication about and throughout the interview process
Even if you know, in the first 5 minutes of an interview, that you’re not going to hire this person, be nice. Don’t be rude or abrupt.
Treat them well and pour a glass of that startup Koolaid!
It’s a great time to share a few stories about your customers, culture, and team. Or pick this person’s brain on experience or insights they may have.
They are going to tell their friends about the interview process.
Being organized throughout the interview process matters also:
Do you follow up in a timely manner?
Do you give clear directions to the office and validate parking?
Do you explain who they are meeting with and what to expect?
I call this the “Undressed-In-The-Examination-Room” effect. The doctor leaves but you don’t know what’s happening next. They do, of course, because they do this 20x/day.
But you are in a medical gown wondering if you should get dressed and leave or wait for someone else to poke and prod you!
Don’t leave your candidates in their dressing gown, uh, metaphorically speaking, of course. 😳
You don’t literally need to build a bench.
(But I’m sure IKEA has some to match the rest of your office decor.)
I’m talking about a sports bench aka a roster of talented folks waiting in the wings!
You may not need a VP of Marketing right now. But if someone intros you with a glowing recommendation, take the coffee meeting, get to know them, win them over, and keep ‘em warm.
Because you will need a VP of Marketing eventually!
So if you meet or interview someone that you really like but there’s not a role currently, don’t tell them “no.”
Tell them “not yet.”
And then track them in a spreadsheet, Gmail label, or Claude chat of potential hires and (have your AI bot) periodically reach out to see how they’re doing and low-key mention the recent mega-huge milestone you passed. 😜
What are some of your favorite tips for hiring? What hiring mistake did you make for way too long??!! Let us know so we can learn from you!
Share with a founder or friend who is in the thick of hiring! ❤️
aka the Customer Playbook no one hands you!
Read MoreAfter years of working with customers on the front lines, I’ve noticed a few quirks.
Things that many founders don’t understand because these are not obvious or intuitive.
(Customer success is different than sales!)
Here are 4 unexpected truths about customers!
And if you want more, check out the Ultimate Customer Success Guide. You know I love Customer Success! 😁
Most All customers are busy. Your product is one of 100 responsibilities. They don’t have time to think deeply and strategically about how they’re using it or how to improve.
They want you to tell them!
This doesn’t mean boss them around. This means guide them on the journey with proactive, helpful, confident recommendations.
Francis Cordon had a guest post about the Customer Journey Map and exactly how to guide your customers!
“Most customers like you do xyz.”
“Most customers like you find the most value focusing on X.”
“Our other customers at your stage start implementing <this feature>.”
Frame it like a question.
Even if you know the answer is yes!
You are asking permission and keeping the customer in charge.
It’s so important I did several slides on it in my Customer Success 101 Training!
This may seem like a direct contradiction to “tell them what to do” but it’s not.
Even when you guide customers, you’re still doing it with a light touch. No “shoulding!” (e.g. You should do this.) Literally, no one appreciates that wording.
When you ask a question, you keep the customer in control AND you make it easy for the customer to share feedback.
If you state something and a customer wants something else, now they have to disagree.
Sometimes that’s too much of a hassle, your customers may be too nice, or they may be secretly annoyed.
Don’t make them work hard or argue with you! Phrase it like a question.
“Is it okay if I check with the engineers and get back to you tomorrow?”
“Does that work for you?”
“Here are step-by-step instructions. Is this what you were looking for?”
Customers are like your bff. They need an occasional vent sesh.
And once they unleash all their complaints on you, they will feel so much better!
You may not 😂 But that’s okay because customers are happy now!
Use Scale of 1-10 to get things back in perspective and remember that angry customers are a good sign!
Here’s the crazy part:
YOU DON’T EVEN NEED TO IMPLEMENT THEIR FEEDBACK 🤯🤯🤯
I mean, hopefully you do.
Hopefully they had some good ideas and hopefully you regularly implement customer feedback.
But for the customer, having someone really listen and appreciate their feedback can be enough.
If you’ve ever complained to your friend/spouse/parent about your day, you understand! It’s very satisfying and cathartic.
Now, if you talk to this customer frequently, tell them they have great ideas, smile and nod agreeably, and do nothing, that’s called grin-f*%king (or gaslighting? did I use that correctly? Gen Z, lmk!). Don’t do that.
But genuinely listening, even if you can’t fix it or take action right away, still has tons of value!
“Thanks for sharing.”
“What else has been on your mind?”
“Appreciate you letting me know.”
The quickest way to calm down an upset customer?
Agree with them!
The human nature default is to defend yourself or your team.
RESIST THIS URGE.
It escalates the situation. They argue more and get more mad!
When you agree, you’re now on their side and you can both move into problem solving mode.
It’s also very disarming because it so rarely happens.
And let’s be real. If a customer is upset, there’s usually a nugget of truth it.
Or a massive boulder-sized amount of truth. Nothing is perfect, especially at a fast moving startup!
Here’s the nuance — can you thread the needle of agreement without throwing your team under the bus?
You are agreeing that their experience wasn’t good and there’s a problem to solve and their pain is real. Without agreeing that your team or product is terrible. 😜
“I’m so sorry that happened. We absolutely need to do better.”
“I agree that this is unacceptable. Can you tell me more so I can figure out the best next steps?”
“You are right. I’m so glad you called.”
What is the quirky thing about customers that surprised you the most? What was your biggest lesson learned working with customers?
Share this with founders who need a customer primer or customer success folks on the front lines! I’d love to hear what you agree with or think that I’ve missed!
The Unspoken Rules Of Getting A Job in VC
Read MoreI often get outreach from people who want to work in venture capital or startup investing.
They usually ask a very thoughtful and kind version of:
How did you break into VC?
How did you transition from startups to VC?
How the hell did you get into tech startups and venture investing after being a Spanish major at a liberal arts college and not being able to turn on your computer at your first job? (LONG LIVE THE AMHERST MAMMOTHS!)
To which I say:
HAHAHAHAHAHAHAHA. Your guess is as good as mine!
And then:
Sorry, I don’t really have much advice since I wasn’t trying to become an investor.
But that’s really obnoxious and not helpful so then I elaborate on the story:
I worked in startups for over a decade as a customer success leader and COO. When I was thinking about my next role, I reached out to David Cummings, who was the co-founder and/or investor of two of the companies I worked for. I wanted another COO role. He asked if I wanted to be an investor.
I didn’t know what that meant, but I said yes anyway, joined the small but mighty Atlanta Ventures team, and have been having a blast ever since. The end. 🙌
So, I don’t have a guaranteed, prescriptive playbook on “How To Get a VC Job.”
But I have talked to a lot of folks in the industry, heard their origin stories, and spotted patterns. Including several that show up in my own story.
So, for all those liberal arts majors wondering if there’s a tech investor role in their future, here’s my best advice!
P.S. Literally, as I was writing this, we opened up a role for a Marketing Manager at Atlanta Ventures!!! How did the O’Daily know before I did?? Ignore this whole post and come work with us! 😉
Contrary to popular belief based on heli-skiing investor photos, most investment firms are pretty small and scrappy.
They are rarely proactively trying to bring on more people. But they will hire if someone amazing comes along.
If you are mid-career and want to transition into VC, it usually happens because someone knows you and your high quality work!
I see it all the time. That new VC partner is:
a former founder that the firm invested in
the CFO at a high performing portfolio company
someone they worked with at their previous startup
It’s rare that a senior level role at a firm is posted online. It is almost always an opportunistic hire through the network. Teams are small, hiring mistakes are costly, and trust is key.
So, in keeping with rule #1 of any job search or career transition, use your network!
Reach out to people that you know, like, trust, and would want to work with. That’s almost always how “breaking in” to something new starts.
Unlike the more senior roles, entry level venture roles are usually posted online.
Usually called an “analyst,” you are prospecting startups, attending events, analyzing deals, and doing due diligence.
Most firms, especially mid-to-large sized ones, have an intentional path to partner.
Come in at an entry level role and work your way up.
VC firms, like any good company, want to retain and promote top talent!
Sometimes the career growth comes across firms which is another good strategy. You don’t want to jump around but moving to a new firm may provide a promotion.
Either way, once you get in, there’s lots of upward potential if you want it.
Maybe this is obvious, but you gotta separate yourself from the pack.
Investors meet many people and have many portfolio companies which also have many people.
So if you looking to be someone who gets the “call from the bullpen” to join a VC firm, focus on doing exceptional work in your current role!
Be the person that everyone wants to hire away or bring with them to their new company. Usually this is a combination of work quality and attitude!
This is my go-to advice for someone who wants to break into tech. It applies to VC too!
Do your same role but for a VC firm.
THEN, you’ll have VC expertise and can transition that into a more VC-specific role.
Here’s how it works in tech:
You work in hospitality but want to transition to tech.
Find a tech firm that serves hospitality customers.
Bring your “industry expertise” to the <your functional area like customer success, sales, marketing, finance> role at the tech firm.
Ta-da! Now you work in tech. Your next role can be at any tech company, regardless of the industry.
Let’s apply it to VC:
What do you do now? Finance, marketing, investor relations?
Find that role at a VC firm and actively learn the overall VC business.
Now you’re well-positioned whatever VC thing you want to do next!
Are you feeling totally discouraged because you’re too old to be an analyst, none of your startup besties are investors, and you’ve worked for big companies or lackluster startups?
One of the classic pieces of career advice I give is:
Do the job you want before you have it.
Andrew Chen’s overview of his journey to becoming a partner at Andressen Horowitz is an awesome example of how he was already a thought leader providing value to startups before he got the investor job.
(Oh, and also built a relationship with a16z over a decade, including being a founder they invested in!)
So how do you do the investor job before you have it?
Introduce VCs and great startups
Help startups in a meaningful way - customer intros, tech expertise, marketing strategy!
Start angel investing
Grow your personal brand as a thought leader and/or community builder
Most people reaching out to me are looking for a job.
But I can’t be a blog for founders without mentioning: YOU CAN START THE COMPANY YOU WANT TO JOIN!
Don’t get me wrong. It’s very hard to start an investment firm. You raise lots of money. Then find exceptional startups. Takes years to know if it’s working. Having startup or investing experience is almost always but not officially a prerequisite.
But founders do “impossible” things every day so don’t let “it’s really hard” stop you! 😉
If you’re an investor, how did you find your first role? What advice do you have for someone wanting to “break in” to the world of venture capital? Share your stories and pass this along to someone on the hunt for a VC role!
The resources I can't stop sharing with founders.
Read MoreThe Summer Slowdown is OVER!
Events are humming, pitch decks are getting tweaked, and I am talking to a LOT of founders who are raising right now.
What am I telling those founders?
It’s a secret.
JUST KIDDING!
Here are the articles I’m sharing most often to help founders think about their pitch, how much to raise, and generally set themselves up for fundraising success!
There’s a 99% chance your pitch is too complicated.
Investor are not smart have a lot going on. 😜 Make it really easy for them to understand what you do.
Think: game of telephone. Could they explain what you do to someone else in a few words after talking to you one time?
Yes, there’s more to your business than just 4 words. But clarity of thought and focus are mission critical to startup success!
#PROTIP: Here’s 6 strategies to find your bite-sized pitch with examples.
Listen. I don’t know how many more ways I can say it.
MAKE SURE TO EXPLAIN VERY CLEARLY AND UP FRONT HOW YOUR BUSINESS IS GOING TO MAKE A LOT OF MONEY.
It literally hurts my heart when founders:
don’t talk about revenue (even though they have it)
focus so much on the “problem” or their product, they don’t mention money
wait for the end of the pitch to start talking dollars
#PROTIP: Talking about money is a great life skill. Here’s why and here’s how.
What should my valuation be??? How much should I raise???
Everyone asks and there’s no correct answer. Just a lot of opinions and tradeoffs.
So get educated on the behind-the-scenes math!
#PROTIP: Here’s how a real VC thinks about valuations (from 2024 but still applies) and the pros and cons of a high valuation you may not have considered.
Arguably the best fundraising article I’ve ever read.
He gives you specific language and tactics on how to pitch, run a process, get investors to compete, and then close.
#PROTIP: Mark Suster is another blogging great on fundraising. Start here and proceed down the rabbit hole.
I know, I know. You’re going to have one meeting and get a $1M check.
Just in case you’re like the other 99.9999% of founders and it takes longer, read this great article from Atlanta startup legend Dave Payne so you can mentally and emotionally prepare yourself for the road ahead!
#PROTIP: Here’s 5 reasons that your fundraise is stalling and what to do about it.
One of my first posts ever sharing insider fundraising info — these are the best, non-obvious tips that I share over and over again!
Get an entrepreneur intro.
Pitch your “worst” first.
Practice Q&A.
There. I saved you from clicking and reading. DO THESE! (And read the whole article for the details.)
#PROTIP: Speaking of Q&A, here are common investor questions (with my unhinged commentary, of course 💁♀️) and 6 strategies to dominate the question portion of a meeting!
Other fave articles? What’s been the best fundraising advice you’ve received?
Comment below or reply to the Substack email and let me know!
Don’t forget to share the love — forward to a founder friend who is fundraising! (Say that 3 times fast 😂)
Kids are back in school, which means the rest of us have officially run out of excuses to skip networking. 😂
Fall in Atlanta Startupland is PACKED. Conferences, coffee chats, pitch practice, and multiple sunrise jogs.
Here are a few events I’ll be hosting, attending, excited about, or all of the above.
(Including an incredible fireside chat with one of the top founders in the Southeast TOMORROW!!!!! See #1 😉)
Lmk if you’re attending or feel free to add other ones in the comments below!
P.S. A little birdie told me to check the South Downtown calendar later this week for movie nights, college football, Braves games, yoga, and other fun! You’ll see me and the fam at Founder’s Green a LOT this fall with a slice, taco, or BBQ in hand.
📅 Wed, Sep 2, 8:30a → TOMORROW!!!!!!!!!!!!!!!
📍 Buckhead ATV Community Center
Literally, the event I’ve been wanting to do for years.
Kristin Oja is a medical and entrepreneurial genius.
And I get to interview her!
We’re talking about:
how she built STAT Wellness from scratch into one of Atlanta’s most-loved integrative health practices with 7 locations across the Southeast
having 3 kids while building a big ass company!
fundraising, expansion, company culture
strategies for founders with ADHD (um, like, 99% of y’all 😂), women over 40 (🙋♀️), and anyone who is stressed and busy (the whole world)!
Come for the coffee. Stay for the unfiltered insights.
📅 Every Wednesday 8:30-10a → Next one is Wed, Sep 9!
📍 Atlanta Tech Village
Wednesd.AI is a free, casual show-and-tell where real builders share how they’re actually using AI (not just talking about it).
Rave reviews, practical applications.
📅 Thu, Sep 10, 12-12:30p
📍 Virtual
Join me and fellow Atlanta Ventures partner A.T. Gimbel for an informal Q&A. Common topics include fundraising, product development, getting your first customers, what we look for when investing, and more.
We do these every month, so if this date doesn’t work, join us in Oct, Nov, or Dec.
📅 Sep 14-16
📍 Nashville, TN
Tennessee’s flagship entrepreneur conference always delivers! Job fair, an innovation night, and Startup Homecoming (corsages and cover bands 🙌).
Don’t forget to (creepily) slow drive by the new Perlant Nashville location!
📅 Fri, Sep 18, 6:45-8a
📍 Meet at ATV Sylvan
Nothing brings founders and investors together like suffering through a 3-4 mile run before 8am. 😂
Meet at Atlanta Tech Village Sylvan, run through South Downtown, and stay for coffee and conversation. Powered by TrackCred and Bluubird.
📅 Fridays at ATV Buckhead
📅 1st & 3rd Tuesdays at ATV Sylvan (South Downtown)
📍 Atlanta Tech Village
Meet founders! Eat food! Open to anyone.
Check out ATV’s events page for the next date near you.
📅 1st Tuesday, 1:30p, ATV Sylvan
📅 1st & 3rd Fridays, 1p, ATV Buckhead
Led by the brilliant Jacey Cadet, get FREE help on your startup pitch. Open to anyone! Practice your 30-second, 1-minute, or 2-minute version, get feedback, and leave less nervous than you walked in.
📅 Wed, Oct 14 - Thu, Oct 15
📍 Woodruff Arts Center & Atlanta Symphony Hall
MARK YOUR CALENDAR NOW. And start prepping!
Venture Atlanta is the largest venture conference in the Southeast, and it’s a great place for a scrappy startup to meet investors or get customers.
#PROTIP: the annual Founder Funder Jog is happening too! New meeting spot: Moxy Atlanta Midtown!
There are rumors which I can neither confirm nor deny that there might be prizes at the jog.
(NOT based on speed - lol! Cool swag giveaways, yall!)
Did I miss something? Always. I can never capture everything going on in this bustling startup world.
Here are a few of my favorite event calendars:
What’s on your calendar this fall? Which of these are you most excited about?
Forward to the founder who keeps saying they’ll network “once things calm down.” (They won’t. Send it now.)
Please feel free to drop other upcoming events with details and registration links in the comments below! 👇
Rebby John asked such an amazing question in his Weekly Update that I scrapped my whole blog schedule to write a novel share my thoughts.
Here’s the question:
As we grow the team, one of my goals is that we want to build Fastlane into the #1 place our employees have ever worked.
What are the attributes / behaviors / mechanisms that (1) enabled incredible workplace culture where people thrived and (2) build a strong employer brand in the market?
Rebby is the founder and CEO of Fastlane AI (an Atlanta Ventures Studio company!), which is growing tremendously fast. Authentic demand, yes please!
Culture is always important, but a good culture with a bad market or product won’t get far.
When a company is growing quickly, it’s more important than ever to focus on core values, hiring, and team alignment.
The thing that could slow you down when the market is hot?
Getting in your own way! 🙃🥴😳
So, Rebby is thinking about the order-of-operations correctly:
1) Get customers that love you ✅
2) Be the most amazing work place so you can continue to serve customers 🛠️ 💪 ✨
Rebby has already done the first two things I recommend:
Set 3 or fewer simple goals per quarter that are communicated clearly
These are not as fun as snacks, scooters, or ping pong.
BUT THEY ARE THE MOST IMPORTANT PART OF A GOOD WORKPLACE!!!!!
They tell you what to do and how to do it.
A job without these guideposts is a wasteland of boredom and apathy with a twice-a-month direct deposit to thank you for your suffering.
(Okay, maybe not that bad, but really annoying and crappy.)
I could do a whole post on why those two things are so important but Rebby saved y’all from that (for now…mwhahaha).
Instead, we get to talk about how to go from Very Good Culture to World Class Culture! Thank you, Rebby!
I’ve been lucky to see a lot of great company culture:
early employee at multiple companies that have scaled quickly while also winning 2 or more Best Place to Work awards
worked for best-in-class companies at the startup, mid-market, and Fortune 500 level
talked to many founders, leaders, and employees who built standout, enduring cultures
The programs, benefits, and strategies varied depending on company size and personality.
But ultimately everything falls into 2 buckets:
Enable good work
Do things for people that they wouldn’t do for themselves (but provide tons of value!)
BONUS: many things fall into both categories.
Let’s talk specifics!
People want to do meaningful work.
They want the tools, direction, and freedom to get shit done!
The best companies to work for — regardless of size — are making it easy to do good work.
As scrappy startups have known for eons (well, decades), this can be free!
Here’s a bunch of ideas around good work at various price points and effort levels:
Set clear goals, priorities, and objectives
Offer purpose and meaning — how is this company making the world better? Doing community service together is an amazing way to build camaraderie and add value to the world!
Autonomy — set the goals, then let people operate. Micromanagement is a great way to make someone want to leave!
Working with other “A” players
20% Time — a Google classic, let people have time to work on things that help the company of their own choosing; Gmail came from 20% Time
Sabbaticals — for example, after 5 years, get 5 weeks off (paid). Phenomenal way for fast growing startups to retain talent. Your great people will work even harder (and stay for the long term). Also, the company will be at a different place in 5 years so it’s a “deferred gratification” perk that incentivizes people now.
Paid time off (PTO) - need to take breaks to do good work, untracked PTO is much easier to manage in the early days. “Unlimited” PTO is not really accurate 😉
Flexible hours — let people work on schedules that work for their life and personal rhythms; don’t be an 8am-in-your-office-chair stickler
No meeting day(s) — having 1 no-meeting day per week is one of the simplest, most impactful ways to prevent burnout with top employees. They want to do great work. Give them time for deep focus.
Well-run meetings or ability to decline any internal meeting (which enforces the “well-run” part!)
Good equipment — quality computers, nice monitors, tech accessories, ergonomic chairs, standing desks, walking pads
Good technology — helpful tools, quality software products, large AI budgets 😉
Saying yes to new ideas or experiments
Career growth opportunities: promotion, new projects, new roles, travel, expanding to new geographies or industries
Education, training, professional development
Manager and leadership development (working for good people is part of good work!)
Snacks, drinks, food — fuel your brain, less time on meal prep logistics
One of my favorite examples from my Pardot days:
We got our cars washed and detailed!
It was such an amazing treat. Park in the deck. Hand off keys. Car is clean when you leave the office!
I’d guess it was $50/quarter. Maybe $100.
I could have afforded it but would have never, ever paid for it out of my own pocket (because I am perfectly capable of washing a car — even though I never did 🙃).
It provided WAY more value and joy than an extra $500/year in salary:
Immediate burst of joy
Felt grateful to my company
Got to brag to my friends how awesome my job was
Appreciated it all over again every time I entered my car for the next week
Much more powerful than a very small increase in the amount of money in my paycheck direct deposit (that I never looked at anyway).
Car washing (^^covered above)
House cleaning
Meals or food delivery
Laundry services ( 👀 A+ Laundry)
Home management or personal concierge (👀 Accomplished App)
For new parents: diapers, meal service, night nurse (plus more parental leave tips!)
Financial education (I still remember our SmartPath sessions at Pardot, what a gift!)
Massages
Fitness classes
Care packages or gift boxes
You can probably put healthcare and 401k in this bucket, but they are often simply “tablestakes.” You need to do them. But most people don’t appreciate them as much as they should, especially given how expensive they are.
These are not my rules, just how humans (myself included) tend to operate! Yay clean car! Meh long term health and retirement. 😳🫠🙃
The fun thing about all these items is that THEY ALSO HELP PEOPLE DO GOOD WORK!
Frees up mental energy. More time to do what matters. Overall well-being and joy that overflows into your professional life.
Many of the “Enable Good Work” items also fall into the “Love It But Wouldn’t Do It On My Own” category:
Sabbaticals
Good equipment for working
Providing time for deep work
Food! (Must. Fuel. Brain.)
Team celebrations and recognizing people’s contributions actually fall into BOTH CATEGORIES!!
Part of good work is the acknowledgement of it, whether it’s at the company, department, or individual level.
Celebrations and recognition can also offer amazing things you wouldn’t do for yourself!
Examples:
Team parties at memorable places — bumper cars, arcade games, cooking class, gun range (true story 😬), escape room, nice dinner, pottery, improv class
“President’s Club” at an amazing location — resort, mountain or lake house, wine country
Peer-to-peer award with gift card, fun swag, socks with your face on them, your own Bobblehead, or 100 other creative ideas!
Workaversary celebrations — including sabbaticals, fancy things like watches, or company-wide recognition of your many contributions
Sales bonuses or challenges — and make it fun! A sales leader I know did a “shopping spree” prize: win a $1000 gift card, 2 hours to spend it.
The ultimate “wouldn’t do it for yourself” celebration — you have to take a trip. Company funds $x, you leave from the office, and report back what you did!
Gongs, ARR scoreboards, champagne on ice for an impromptu toast
Community service also fits in here! Great team building and something you might not do on your own. Celebrate your abundance by helping others!
The list is endless and I’m sure I’m forgetting some favorites.
What have been some of your favorite best-place-to-work traditions, perks, or benefits? The more creative and memorable, the better!
Coming Soon:
We’ll also answer Rebby’s next question about employer brand building and share some common mistakes that well-intentioned founders make!
Look forward to the Valley of Despair!
Read MoreYou may not have heard of the Dunning-Kruger Effect.
But you’ve definitely experienced it.
It’s one of my favorite ways to understand the startup journey.
Shoutout Ashley Levine who first taught me about:
Mount Stupid
Valley of Despair
Slope of Enlightenment
Yep. Right in this very moment, I can practically guarantee that you and I are both on Mount Stupid in one way or another!
Here’s what Dunning-Kruger is, why it’s awesome, and how it helps at startups!
The Dunning-Kruger Effect is a cognitive bias where people with low ability in a specific area give overly positive assessments of their ability. Also, people with high ability in a specific area tend to underestimate their abilities compared to others.
You can read the nerd stuff (research results, critique, methodology) here.
THEN, there’s the internet version which Gemini tells me was mostly a riff off the Gartner Hype Cycle 😂
That’s the one I like, pictured below.
Never let actual science get in the way of a good faux-science business parable, I always say!
David Dunning and Justin Kruger didn’t actual come up with the terms Mt. Stupid or Valley of Despair or the Slope of Enlightenment. That was The Internet, of course!
Here’s how I understand the Dunning-Kruger Effect.
First, you think you know.
“I totally got this,” you say. “How hard can it be?”
LOLOLOLOL. It feels so good when you’re on Mount Stupid.
Unfortunately, as you proceed, you realize that you are not, in fact, as knowledgable and smart as you thought.
You are plunged into a pit of sadness and hopelessness.
“How am I ever going to learn all that I need to??”
Welcome to the Valley of Despair.
BUT WAIT!
You can learn. It’s slow going. But over time, you can inch your way up the Slope of Enlightenment.
Then, of course, you get to the Plateau of Sustainability which I didn’t really know about until just now so I don’t have many good jokes about it. Sounds nice though!
A startup is basically a never-ending cycle of Mount Stupid → Valley of Despair → Slope of Enlightenment → Plateau of Sustainability, with a lot of painful time spent falling off Mount Stupid over and over again.
Dunning-Kruger is not really a psychological phenomena (for our purposes), but a hilarious, universal language to describe the ups and downs, aggressive learning curve, and confidence roller coaster of a startup.
Examples:
Instead of: “I made a horrible, ego-driven misjudgment and now I’m embarrassed, angry, and overwhelmed.”
Use: “UGH. Mt. Stupid and I didn’t even realize.”
Instead of: “I’m sure this will be easy. We’re really good at it.”
Use: “Am I on Mt. Stupid? Or is this the Slope?”
Instead of: “I am so discouraged, I don’t know even know where to go or how we’re going to fix it.”
Use: “I am in the Valley of Despair right now!”
(Note: I use this frequently when I’m packing the car before a family trip and I don’t know how the hell we’re going to fit 500 items into a single trunk. My husband knows that I will journey through the Valley of Despair but prevail on the Slope of Trunk-Barely-Closing, I mean, Enlightenment. Those 10 minutes in the Valley are very dark, everyone should stay out of Mom’s way, and suggestions are NOT welcome. 😂)
So the next time you make an asinine mistake or it’s a really hard day of “learnings,” just name it.
You’ve been hiking Mt. Stupid.
Declare that you are in the Valley of Despair.
It’s a moment in time, not a forever state.
It’s also hard not to crack a smile.
The tough moment gets easier.
And the Slope of Enlightenment is just ahead. ⛰️
Any favorite faux-science business parables? Had you heard of Dunning-Kruger before?
Bullet point highlights on getting more customers and funding!
Read MoreLast week, I teamed up with Jess Owens for a Founder Learning Session on personal brand building and how it can get customers and funding!
We covered:
why social presence matters more than you think
getting results when you’re tight on time and money
how it actually speeds up your fundraise
Here’s the FULL SLIDE DECK, with a bulleted summary below.
Not included: excellent mom jokes, excellent audience questions, and the screenshots of fun wins! Can’t get everything from the Clif Notes AI summary! 😉
Not a vanity project.
Builds trust
Establishes credibility
Keeps you top of mind (more effective + easier than nurture campaigns)
ALL OF THOSE THINGS → Shorten the sales cycle
Cost-effective distribution channel
Outperforms company brand 5-10x
Humanity is your edge in an AI world
The biggest myth about personal brand?
That you need to have great (smart, unique, well-produced) content.
You don’t.
CONSISTENCY. → most important!!!!! 1x/wk over years is better than 5x/wk for a month.
Start small, add slowly. → pick 1 thing to try, make it easy!
Obvious is okay. → see “easy content” ideas.👇 No rocket science!
Easy content → upcoming events, event recaps, favorite resources, customer wins, industry trends.
Focus on your niche. → you don’t need to be famous, only known by your ideal audience!
Test and iterate. → see what works and what you like. brand is built through action not thinking.
Want the full playbook? Read How To Start Your Founder LinkedIn Journey.
Here’s the part investors don’t tell you:
Your personal brand is doing work before you walk in the room. They’ve already looked you up. What did they see?
A strong personal brand:
Establishes trust, track record, and communication style
Leads to efficient customer growth, better CAC
Builds business moats
…aka a FASTER FUNDRAISE!!!!!!
You also need to have a great business. Brand alone is not enough. But, same as the customer sales cycle, personal brand can attract, filter, and expedite a deal!
AI, an intern, an agency. Whatever gets momentum going!
Not in a mean way. In a “you won’t have hate mail from one typo” way, so don’t let perfect be the enemy of published!
Pick the absolute smallest thing you can commit to and get started!
I firmly believe that a personal brand is like a marathon.
Anyone can do it.
No marketing genius or elite athletics required.
What IS needed:
willingness and desire for the outcome
commitment to the work over months and years
We may not all qualify for the Olympics or get 1M followers, but you’ll be pleasantly surprised what’s possible when you follow a plan and do a few runs/posts per week!
“Do or do not. There is no try.” -Yoda
What’s stopped you from posting more? And if you’ve built a personal brand, what worked?
Send this to the founder with 200 LinkedIn drafts and zero published posts! 😜
P.S. Want more on this? Check out Why Personal Branding Matters, For You and Your Company.
What the best know about winning, rest, competition, and how to keep going.
Read MoreSports are a fave topic on the O’Daily.
SO MANY PARALLELS BETWEEN STARTUPS AND SPORTS!!!!
Also, I just love them.
Running, Ironmans, basketball, rugby, Ultimate, softball, and that doesn’t include being a 1990s Braves super fan.
(Anyone else still love the “Always Coca-Cola” jingles from 1990s Braves radio?? Okay, just me.)
What learned from my dad is via sports and I’ve already shared 4 lessons from being an Ironman that apply to startups.
But wait…there’s more!
Here’s 5 more lessons from sports that apply to startups. On your mark, get set, go!
The best way to get better?
Play with people better than you!
I love training with people faster than me. I love working with people smarter than me. I love seeing what is possible and being pushed by their excellence.
True in business too!
Competition drives:
Efficiency
Performance
Lower prices
Creativity
Just look at all the AI progress as Anthropic, OpenAI, and Google duke it out.
So that defender who made you work extra hard to score?
The runner ahead of you on all the hills?
The other executive who gets better results?
The company in your space whose marketing is crushing yours?
Thank them!
They’re raising the bar and giving you a reason to work even harder and smarter.
Competition isn’t bad, it helps you get better and, in the world of startups, it’s fantastic market validation!
My triathlon coach Matthew Rose used to say this.
Usually when I was complaining about being “too tired” to hit a pace or wattage.
Also to prep me for the ups and downs of race day, like being in the depths of despair at mile 10 of the Ironman marathon (only 16 miles to go! 😬😂).
Ideally, you feel great on race day.
Ideally, you walk into a client meeting and you’re in the zone.
But if you are tired, sick, nervous, or just don’t feel as amazing as you want, YOU CAN STILL EXECUTE!
This mindset is at the heart of how great founders overcome Imposter Syndrome:
You don’t need perfect conditions.
You DO need to show up and keep going.
And if you can shift your outlook from “this is terrible and I suck” to something with more hope, determination, and positivity?
All the sudden, the legs feel lighter at mile 11 and you realize that you can still close a deal without the perfect slide deck!
I came off the bike in 10th place in my age group. Not good.
But you never know what will happen…
Turns out, my not-good bike meant my legs were fresh. I ran one of the fastest half marathons of the day, passed 6 women in my age group, and snagged 3rd place and my first trip to 70.3 World Champs!
At the 2025 Ironman World Championships, the women who were in 1st and 2nd place both dropped out (brutally hot day), which meant the athletes in 3rd, 4th, and 5th ended up on the podium aka in the prize money, baby!!!!! 💪😎💰
I worked at two companies that were “underdogs.”
Competitors raised more money, spent more on marketing, hired more people, and built more features. (Or at least that how it felt at the time!)
If we had thrown in the towel because we were “behind,” we never would have been acquired by top tier public companies!
Turns out, some of those competitors were spending too much and it wasn’t sustainable.
You never know what will happen…
My dad and I used to run together on a 2 mile loop in our neighborhood. At the finish, we run up a big hill and turn onto our dead end street.
The game? Pick up the pace. Faster and faster. Pass our driveway. Alllll the way to the end of the street. Sprint finish!!
Who won? I don’t remember.
That wasn’t the point. It was about the fun of competing, pushing yourself, spending time together, laughing while smack talking about the next run.
Sports (and life!) can be joy, misery, or both.
But most of what you feel, day in and day out, depends on you.
If the only goal is to win, potential is limited. A binary outcome. Your growth (and happiness) is capped.
If the goal is to appreciate the experience of playing and competing, you always win.
And I don’t mean the score.
You win because of how you feel about yourself, what you learn, the memories you made.
BONUS: You also play better!
Joy makes consistency and sustainability easier, which are two of the biggest factors in long term outcomes.
It also lightens the load. You let go of pressure, attachment, stay in flow, and actually perform better.
Are you thinking about that pitch competition as life or death? Or can it be a stage party with some butterflies in the stomach and good stories?
If you don’t sell your company for $1B is it a total failure, or will you love the impact you made along the way?
You know what’s harder than pushing through?
Taking time off. Ending a workout early. Giving yourself an extra rest day.
Any elite athlete will tell you, recovery is as important as training.
Sleep, nutrition, off days.
The best at their sport are also the best at recovery.
In the days leading up to your target race, you do less training so your body can be rested for the race — a taper. Mentally, it’s WAY harder than a big training week.
You’re cranky, anxious, out of rhythm. There’s a friendly term in the industry called a Taper B!tch. And it applies to pretty much everyone 😁
Some people can’t do it. They can’t handle the rest, train too much, and never have the race they are capable of.
Imagine: years of work but you never live up to your potential because you can’t chill for 1 week.
Sound familiar to, gulp, any founders out there?
Taking time off is one of the hardest things for founders.
Yet, I consistently hear from founders who say that taking time away, even a day or two of unplugging, gave them huge amounts of energy and unlocked key business insights.
Many founders can’t make themselves do it.
And just like athletes, they never achieve their full potential.
Because the best athletes and founders manage the fear, trust the process, play the long game, and understand the performance value of intentional recovery.
You’re not being lazy. You’re doing the hard work of getting better.
What lessons resonate the most for you? What have you learned through other areas of life (music, art, plants, school, building things, parenting) that help you navigate startups?
You’ve had many convos but no bites. Here's why (and how to fix it)!
Read MoreYou’ve been having lots of convos but no bites. Not even a nibble.
What is going on??? Does everyone know but you??
Here’s 5 common reasons why your fundraise might be (verrrrrrrry) slow — and steps to take to speed things up!
I know you read about a company in Techcrunch who raised $100M with no revenue and now you’re fired up to do the same.
(P.S. It’s probably not true.)
Every founder wants a lot of money and high valuation. But there’s also downsides!
Including that investors will pass because the valuation is too high.
Even when they like you and your business.
They don’t want to damage the relationship (or their reputation) with an offer that’s too low.
But, Kathryn, I didn’t even say a valuation!
Reminder: valuation and amount your raising are directly connected.
THE FIX: Raise a smaller amount of money/lower the valuation. Get more investors interested. Let them compete the price up. Here’s how investors think about valuations!
tl;dr: you’re asking for too much money given your revenue or customer count.
Founder: But I’m pre-seed??? I don’t have revenue or customers.
O’Daily: You do need to have a lot of data and compelling talking points.
Founder: But I need to raise money to build the thing to get customers!
O’Daily: You can almost always get customers to pay for something. Even if it’s small, manual, or consulting services.
Founder: Fundraising is a full time job. I haven’t had time to get more customers.
O’Daily: Truth! So what if you spent this time on getting customers instead??? More revenue now, easier to fundraise later.
THE FIX: Get out there and get more (paying!!!!) customers! If they won’t pay, it’s not valuable. Many creative ways to pre-sell before a product exists: consulting services, tech front end with a manual backend, vibe coding, and more!
Another way to say this is that your idea may not be “venture-scale.”
Venture-scale means that you could generate $100M in annual revenue within 10 years with good margins.
THERE ARE LOTS OF GREAT BUSINESSES THAT ARE NOT VENTURE-SCALE!!!!!!
Look at all the small-business-owner millionaires! (That you’ve actually never heard of because they’re not announcing on tech news that they’re rich 😉)
Agencies, brick-and-mortar stores, consulting, home services, highly niche tech are all examples of businesses that are rarely a fit for venture funding (but can make the owners lots of money)!
Yes, there are exceptions and often these businesses will have an exit, but they grow through customer growth not venture investment.
THE FIX: Take a hard look at your goals. Do you want to build something venture-scale? If so, iterate to a larger market or idea. Are you passionate about the current idea? Grow the business through customer revenue or bank funding.
It used to be that slides could look messy and disorganized. AI solved that.
(If they don’t, um, AI skillz?!? Ya, you need those.)
But your deck could be scaring off investors if the narrative, data, vision, and through line is verbose, disjointed, or underwhelming.
Or you forgot to —GASP! —talk about the money!!!!!
Here’s what can happen if your pitch deck is confusing:
“Hmmm, I don’t understand what this company does.” ➡️
“Why do they need so many slides to explain their business?” ➡️
“Is this how the founder always communicates?” ➡️
“Maybe they don’t know their own vision?” ➡️
“Customers and potential employees will be confused.” ➡️
“This is a red flag.” 😬😬😬
THE FIX: Focus on tightening your elevator pitch. Can’t do it in 4 words? You have more work to do. Avoid these 3 red flags, get help from experts, and practice, practice, practice!
In the early stages, investors are mostly betting on founders.
Be someone they want to bet on!
If you’re wishy-washy, thinking small, not following through, uninspiring, don’t know your business, or can’t get people interested, that’s a big concern.
Highlight your strengths like:
Vision-casting
Competence
Energy
Determination
Attitude
Ambition
Sales and stortytelling
You don’t have to have all of them. But you should have a lot of them. 😉
There’s also a fine line between confidence and arrogance. You want a founder to be confident enough to lead, sell, and take action, but still being open to learning and advice.
So bring the energy, ambition, determination, positivity, and belief!
And if you have it, but it’s not coming across, we’ve got tips to help you.
THE FIX: Use these strategies to better project confidence and build credibility. Remember: imposter syndrome is totally normal for founders. Here’s 4 ways top CEOs overcome it!
What helped you fundraise? If things were going slow, what did you adjust to get fundraising momentum? Any other reasons you’ve seen for a fundraise to not be going well?
Want to stay up to date? New blogs come out weekly.