Transitioning Away From Founder-Led Sales? (Read This First!)
5 key learnings to smooth the way!
Read More
5 key learnings to smooth the way!
Read MoreOne of the most important transitions in a startup journey is when the founder hands off day-to-day selling.
In the beginning, the founder needs to sell.
If the founder can’t sell the product, no one can!
(HARD TRUTH: If you are not getting good sales results, “hiring a sales person” will not solve this. Do more customer discovery to find the authentic demand and/or work on your own sales skills!)
At some point, the founder-as-the-only-sales-person is not scalable. Deals fall through the cracks. The founder is needed elsewhere. You have too many leads for one person.
It’s time to hire your first sales person!
I have seen this transition with many, many companies, spoken to founders, and picked the brains of successful “first” sales people.
It’s a critical time with a lot on the line.
Here are 5 things to know so you’re set up for success as you take the leap from founder-led sales!
Your first attempt is probably not going to work out.
I know, I know. I said this blog was about setting you up for success.
Here’s the thing — in order to be successful long term, you need to expect some false starts in the short run.
You will read every blog on scaling sales, talk to mentors, get advice from other founders, interview lots of great sales talent, and 90% of the time, you’ll make a change 30 to 90 days later.
IT’S NOT YOUR FAULT.
There is something nuanced about your business, customer, and sales process that no one knows yet!
You hire a Business Development Rep (BDR) but your customers hate cold calls.
You hire a hungry, scrappy hunter, but you need industry experience.
You hire someone with industry experience, but you need a scrappy hunter.
You hire a full-cycle sales person but your customers want to self-serve.
You hire an SMB sales leader but your product is actually enterprise.
It worked for lots of other companies. But it didn’t work for you.
THE ONLY WAY TO KNOW IS TO TRY.
You test a thoughtful hypothesis and expect the bumps and look for the learnings!
If you’re the founder who makes the right hire for the right process at the right time on the first try?
Buy a lottery ticket, you lucky bastard!
I’ve heard this from successful first sales reps over and over:
You can’t sell how the founder sells.
The founder is a natural athlete. The first sales person is a student of the game.
Maybe the founder is a sales genius. Maybe they learned to sell along the way.
Regardless, they have the unrepeatable superpower of being The Founder.
They have an intuitive understanding of the customer and problem. They know every nook and cranny of the product. They can tell a heartfelt how-it-came-to-be story.
They probably don’t even know why and how they are good at sales!
The first sales person — the ones who are effective — are avid learners who believe in a sales process.
They soak up the learnings from the founder. Listen to calls, review transcripts, ask about previous deals, shadow whenever they can.
Then turn it into their own sales playbook, often using a framework and process that’s been effective at a previous sales job.
They take the founder’s art and turn it into their science.
A pattern I’ve seen from first sales reps who are successful…
They “get” it.
Your website sucks, the messaging is confusing, your product is barely functional, and this person says, “I totally get it. I see the need. It’s going to be huge. I believe in this.”
Maybe they were a user, from the industry, or they’ve experienced the problem themselves. In some way, they have an inside understanding.
Of course, someone can “get” it and not be successful.
Someone can also have no previous knowledge of the industry and crush it.
(I’ve seen both. See #1 for “Expect A Learning Curve” 😉)
But finding someone with confidence, enthusiasm, and clarity for what you’re building is HUGE.
They bring “Founder Energy” (and customer empathy!) without being the founder.
Some of what you’re doing isn’t working.
Yes, you. The founder. Enough stuff is working that overall things are good.
But there’s a slew of wasted time and money.
You just can’t see it.
But the new sales person can.
They will be able to audit the sales process with a fresh perspective.
Are you ready to implement someone else’s suggestions and let go of things that are not working?
Can you let someone else talk to your beloved customers, close your hard-fought deals, and make mistakes along the way?
It’s a tricky balance. You are the expert. Sales are important. A new hire will have a learning curve.
And if they’re f***ing up you need to know quickly.
But no one likes micro management or having reasonable ideas shot down.
Especially not if they’re a really good sales person who is committed to you and the company!
As the founder, make sure you’re ready to loosen the reins, learn how to not be the bottleneck, and for goodness’s sakes, resist the urge to swoop in and shit all over everything.
Avoiding seagull management is key to a smooth sales transition!
A successful first sales person must want to be at a startup.
Not a make-us-all-billionaires-in-1-year, I-had-a-friend-who-was-at-Facebook startup.
But a real, messy, winding road, no guarantees startup.
Startups mean:
Patience — lots of learning, experiments, and ambiguity along the way
DIY — sourcing your own leads, making your own slide decks, doing your own demos
Financial flexibility — low base salary with high uncapped commissions
Long term upside — HUGE financial and career opportunity
Great journey — with the right team, the startup ride is amazing. Impact, learning, memories.
If someone asks for a super high base salary and needs a sales engineer to be on demos…they are not your person.
In a few years, they may be a good enterprise rep, but today, they will not be able to hang.
A trend I’ve seen across successful first sales reps — they can play the long game and weather the ups and downs, both emotionally and financially!
Of course, part of the deal is that they are rewarded gloriously for their persistence and patience with compensation and career opportunity.
Your best sales rep should make more than anyone else in the company!
After a 1 year vesting period (protecting the company against hiring missteps), they will have a nice stock option grant too.
For their time grinding it out in the trenches and figuring out a successful non-founder selling motion, they have more than earned it!
Transitioning from founder-led sales is a big change but you WILL figure it out!
Think of the thousands (millions??) of successful startups who have come before you who did it.
Always happy to chat about specific scenarios or discuss at Office Hours or Atlanta Tech Week (happening this week)!!!
What other trends or strategies have you seen with a successful handoff from founder to first sales person??
Special thanks to Kasey Hardin, Brett Lange, and Kathryn Farrell for their insights for this post! 🙏🙏🙏
7 easy strategies used by top founders on LinkedIn.
Read MoreBuilding your personal brand can be wildly helpful to your company.
In many ways, a founder’s brand is more powerful than their company’s brand.
It can be intimidating at first but with a simple starting plan, you’ll gain momentum and confidence quickly!
I’ve been posting on LinkedIn 2x/wk for several years.
I’ve made great connections, heard from hundreds of founders that appreciate the stories and tips, established credibility as a newcomer, and stayed “in touch” with thousands of people.
It would be impossible to get that reach through events or coffee meetings alone.
I have learned a lot along the way, including from folks WAY BETTER than me like:
If you want to get inspired, see different styles, or take notes on best practices, check out their content!
Shannan Brooks and Evie Lutz are two behind-the-scenes geniuses that have also been hugely influential.
Since LinkedIn is such a popular channel for business folks, it’s a starting place for many founders building a social presence or personal brand.
Here’s what to know about posting on LinkedIn so that you can effectively build your brand.
MOST IMPORTANT STRATEGY: Just get started.
After that, if you’re spending the time anyway, might as well know the tips and tricks.😉
Here are 7 straightforward strategies to maximize your impact on LinkedIn!
P.S. Who’s going to Atlanta Tech Week next week? What events are you going to? Lmk if you’ll be at the Founder Funder Jog or my Startup Summer School sesh on Building a Billion Dollar Business so I can look for you!
Okay, back to LinkedIn!
Seth Radman, with 20,000 followers, said he spends 70% of his energy on the first line of a post because it is 10x more important in driving engagement.
It’s called a “hook” and the best ones are usually controversial, surprising, or peak your curiosity!
If a post isn’t performing well, Seth will swap out the opening line. A/B testing in real time.
Go check out the opening lines of top influencers. They are SO good.
One of my favorite examples is “These women are drug dealers.” (Full credit to Lauren Goodell for that one!)
It was a recap of a biotech founders lunch that ended up with 16,000 views. 😉
It’s better to post 1x/wk for 6 months, than every day for 2 weeks and then go dark.
Why?
You stay “top-of-mind” with your target audience over time
LinkedIn rewards consistency by showing your posts to more people
If you are going all in for maximum followers and views, posting daily is the gold standard.
But this is really hard to do for the long term unless you enjoy it, you have help, or you’re just a total animal (that’s a compliment!).
There’s a reason I put cringe-y me-drinking-coffee photos with LinkedIn posts…people love photos and therefore “The Algorithm” does too.
Not ready to see your face all the time? (Trust me, I get it.)
Other non-selfie options include pictures from events, group shots, charts, screenshots, quotes, or other visual digital content.
You don’t have to have an image on every post but including them will usually increase engagement.
BONUS: if you have an image, you can now re-post to Instagram too!
Here’s the secret from the content pros — have something that performs well?
Do it again!
Not the exact same thing.
Use the same opening hook with different content.
Do more content on that topic.
Recreate that length or style of post.
You’ll notice the best creators do this frequently.
They’re also looking at other people’s content and riffing off their top posts. Nick Maggiulli shares good examples (and a critique) of this strategy.
Piggybacking on a recent trend is another common content strategy. Do your version of the trend or share thoughts on a topic everyone is talking about (tariffs, anyone?).
Reply back when someone comments! Comment on other people’s posts!
And for goodness sake’s, keep it positive.
I follow the golden rule:
If you don’t have anything nice to say, don’t say anything at all…because you never know who is a potential customer or employee!
Once you’re a regular LinkedIn-er, it’s common to ask a question or two at the end of a post to encourage engagement and comments.
You know why people do that annoying thing where they put a blog post link the comments section instead of the actual post?
LinkedIn *hates* external links. It wants as much on-platform content creation as possible.
I read this in their documentation:
You’re blogging on Substack?? Yuck. No thank you. Bring that to LinkedIn and we will reward you generously by showering your posts with views and engagement.
I also saw this weird sign:
DON’T NEVER LEAVE. -Hotel California & LinkedIn Algorithm
You know how I said photos and avoiding external links improves performance?
That may not be true forever.
As consumer behavior evolves, so too does the LinkedIn algorithm.
Recently, video performance shot up as LinkedIn added more video features (thus, encouraging video content).
How do you know what the LinkedIn algorithm likes?
Track your own performance metrics
Periodically review LinkedIn “best practices” via marketing gurus or other influencers
Read the code base (Seth Radman, engineering whiz, got insights from this!)
That’s it. Go out there and do it!
You’ll figure it out as you go.
The best way to do LinkedIn is to…do LinkedIn!
Post something today (and tell me) so I can give it a like and a comment!
Do you post regularly on LinkedIn? What advice do you have for those getting started? Any key strategies that I missed? If you want to post more but haven’t, what’s getting in the way??
Universal #protip: Learn from smart people whenever you can!
That’s why I like to pick the brain of fellow partner at Atlanta Ventures, A.T. Gimbel, every chance I get.
(His Substack, Startup Strategies, is excellent! Check out this one on what a term sheet can tell you about an investor.)
I’ve shared acquisition advice before like insider insights (that you may not expect), how to get top dollar for your company, and how to make the most of the opportunity post-acquisition.
When A.T. and I chatted about acquisitions, I learned even more!
Not only does A.T. have a front row seat on the startup side, he has been on the “buy” side of the acquisition process and done merger and acquisition (M&A) due diligence.
Here are 6 *more* strategies — inspired by A.T. 🙏🙏🙏 — that drive a successful acquisition, especially during negotiation!
Not thinking about an exit yet? I’ve included #protips on how these strategies apply across Startupland.
Strategics (a company acquiring you as a value-add product, because of your similar customer, or other strategic alignment) are more flexible on price than private equity (PE) firms.
Strategics want you for you.
A PE firm’s whole business strategy is around optimizing financials so price matters a lot.
You can still use normal leverage and negotiating strategies with both but be aware of the difference in perspectives and motivations.
Related — know if you’re a rounding error. If you’re selling to a multi-billion dollar company, the difference between $40M and $50M is immaterial. But to you and your team, that’s life changing.
Conversely, if you’re selling to a midsized startup, an extra $10 milly is probably meaningful to them.
#PROTIP
Always understand what the other party cares about and is measured on. Applies to your customers too!
As tempting as it is to keep your company perfect and rosy, it’s best to disclose any potential issues before signing the letter of intent (LOI).
Negotiate hard at the LOI stage when you have the most leverage. After the LOI is signed, the price rarely goes up but often goes down.
(Remember — the acquiring company likely has a team of M&A experts, who know exactly what to look for and do negotiations all the time.)
You don’t have to share all the gory details, but if you don’t disclose meaningful items before the LOI, they will surface during due diligence, and they will be used to drop the price.
Examples:
a line of credit
messiness on the cap table
upcoming customer churn
contracts missing important terms
unusual employee agreements
None of these are dealbreakers, don’t freak out. Just make sure they are mentioned (ideally in writing) prior to the LOI so the “big guys” can’t bring them up later as a reason to discount your company!
#PROTIP
True for any negotiation, including customer contracts or employee job offer. Surprises kill trust. Proactive discussion builds trust and mitigates issues!
A broker, legal counsel, or someone who will not be around after the deal is done is a great person to be the designated “bad cop.”
You will be working with this group after the deal so you want to stay on good terms (being nice matters!) while driving the best deal.
Always negotiate — even if you don’t love it. You owe it to yourself and your team to get the best price and terms.
#PROTIP
I often see this in startup leadership too. The COO, CFO or other exec tends to say “no” or implement hard decisions while the CEO focuses on vision and building relationships and alignment. Sometimes it is flipped if the CEO is a very challenging personality. Another exec will be the “good cop” to balance.
Get someone on your side who knows the insider strategies.
Make sure they actually know! (A bad consultant is worse than none at all. And def doesn’t need to be a consultant.)
I’d start with:
Other founders, especially with exits (good or bad)
Experienced startup lawyers
Friends who have done M&A at large companies or consulting firms
VCs or investors with M&A experience
Always talk 1:1. What’s shared publicly may not be the whole story.
Develop enough relationships so you can have a few folks on speed-dial for quickly evolving negotiations. (Phone a friend - acquisition edition!)
Everyone will have a different lens based on their personal experience. Understand their bias, get several perspectives if you can, and always calibrate with your own intuition and judgement.
#PROTIP
Learning from people who have gone through it or see the inside of a lot of businesses is a great strategy across every area of startups!
It’s a common strategy for the “big guy” to try to separate a zebra from the herd.
They call you and your co-founder separately and ask you each what the valuation is. And it’s urgent!!!!! So you don’t have time to talk and align. 😉
(I have literally heard this exact story from a founder during a fundraise.)
Or, they tell you that they talked to your lawyer/co-founder/childhood friend who said XYZ while you weren’t there.
Or they want to “hop on a call” even though your legal counsel isn’t available.
Or…any other way to split people up to get the best terms!
Always negotiate all the terms in full.
Don’t get dragged down a rabbit hole that doesn’t matter or let someone talk about one part of the contract (or a “hypothetical” contract) without seeing the whole thing.
Certain terms may or may not matter depending on how the whole contract is structured.
Examples:
Price. Is it a stock or cash offer? A lower price paid in cash might be better than a higher price that’s stock only.
4 Year Earn-Out (aka you have to stay for 4 years before you get paid). Is 90% of the payout in year 4? Or is 90% after year 1? Big difference.
Earn-Out - Part 2. No amount of $ could make you work at a big company? Then don’t worry about the earn out!
See how the full picture makes a huge impact on the details of the negotiation?
Don’t get distracted by one-off items. Get the entire offer before talking specifics!
“It really depends (on the full offer),” is a go-to phrase.
#PROTIP
Knowing the strategy helps prevent it! Get clear on what matters to you — and what matters to other stakeholders like investors or co-founders...especially if you care about different things.
Being acquired can be an amazing outcome for a startup!
It can also be stressful and you want to make the most of the opportunity.
There will always be learnings along the way and things you wish you did differently, but learning from others and being prepared makes a big difference!
Good luck and feel free to add me to your “Phone-A-Friend” list. 😉
What other advice do you have on acquisitions, negotiations, or other dealmaking?? Do you agree or disagree with these tips?
Like most parents, I have it all figured out.
HAHAHAHAHAHA.
For real though, being a working parent is hard and I looooove me some systems and best practices.
When home life feels calm(ish), I can bring my best self to work — maximizing time, energy, and focus on founders.
It’s true for all working parents — but especially so when you’re a founder and your family isn’t the only source of chaos in your life. (Ahem, startups, ahem.)
Routines are key and my husband and I have tested and iterated over the years with our two kids, now 5 and 7 years old.
It’s different for everyone (and different life stages) but here’s what works for us that might spark an idea for you!
Spoiler alert — these are helpful for anyone, even if you don’t have kids. Adults like routines too.😉
Here are 5 things we do every week as working parents to save our sanity and keep a connected, happy family life.
(Estimated Time: 1 hr/week)
The most stressful time of day for a parent?
30 minutes before dinner is ready when everyone is whining and hangry, including you!
We used to prep staples every week.
This works great…unless it’s 6:30p, you just got home from soccer practice, and DINNER IS NOT READY AT THAT EXACT MOMENT.
(But, boy, do you have a lot of great cut up veggies in the fridge! 🙃)
Our new strategy?
Make a bulk meal on Sunday that will get us through at least 2 dinners that week.
We have an arsenal of quick meals for 2 other days, 1 night of leftovers, and then we’ve made it to the weekend! 😅
Here’s a few meal ideas (+ easy lunches for work) but happy to share more if folks are interested - just reply or comment.
(Estimated Time: 15 min/week)
On Sunday afternoon or evening, we always review the upcoming week as a family.
Boring, simple, and absolutely essential to our sanity and well-being.
We pull out our phones, look at work and personal GCals, and go through day by day.
Who is doing daycare/school pick up and drop off?
Who has what events or practices on what days?
Any special events for school, work, or otherwise?
What meals on what days?
Workout plans?
Other errands or appointments?
We usually find a few spots where we need to:
coordinate further (aka last minute call to grandparents for help 😂)
have a to-do we forgot about (buy snacks for the soccer game!!)
clarify who is doing what (glad we didn’t leave a child at daycare all night)
The kids participate so they know what’s happening and will chime in with things like, “My library book is due that day” or “I have Show and Share on Friday.”
(Estimated Time: 10 min/day)
Every night at bedtime, we gather in the kids’ room and share:
Rose - something good from the day
Bud - something you’re looking forward to
Thorn - any upsets or frustrations
Daily stand up meets gratitude journal.
We like it as a:
Connection point
Debrief and reflection on the day
Source of info about how our kids (and partner!) are doing
Way to reinforce our values (e.g. my Rose was running with friends, my Rose was how well everyone did on the car trip)
Lest you think we are Leave It To Beaver, it also involves arguing about who goes first and annoyance over interruptions.
My thorn today is…yelling at my kids during rose, bud, thorn. 😉
(Estimated Time: 30 min to setup, then 1 min/day)
What’s more annoying: picking up after your kids or reminding them to pick up after themselves?
TRICK QUESTION.
They are both f-ing annoying!!!
Enter the handy index card, our one-two punch solution for kids chores and the daily reminders of “yes, even today, you have to brush your teeth, and also every day for the rest of your life.”
How It Works:
Write and/or draw pictures of each task on an index card.
Parent lays out the appropriate cards depending on time of day, activities.
Child has visual “checklist” of tasks that need to get done.
We put ours on the kitchen table and the kids put a token on the card when it’s completed.
Does it need to be cards? Nope. Any kind of visual, analog schedule or chart can work.
Like any new system, it can take a bit of time to implement and get user adoption, but as a startup founder, you’re familiar with that! 😉
(Estimated Time: no extra time, swap out other activities)
I’d like to share a retro invention that will blow your mind:
BOOKS!
Books are really awesome and kids love them. Books calm my kids down, while screen time ends in shouting or crying.
Audio books on car trips
Free from the library
Everyone can listen together
“Books in bed”
Too tired or busy to read to your kids? Let them read to themselves in bed.
We stumbled into this “treat” that our kids love. Lazy parenting FTW!
Read at dinner
Tired of fart jokes at dinner? No time for bedtime reading? Read aloud to your kids at dinnertime!
We do a chapter book that everyone (read: me) enjoys, 1 chapter per night.
We are missing out on building conversation skills but sometimes everyone (read: me) needs a break from non-stop bickering talking.
If you’re worried that I have no qualifications to give parenting advice (valid) and want to know what experts recommend, here are two resources that I love!
The 3 Big Questions For A Frantic Family by Patrick Lencioni (business parable guru - s/o Ellen Twomey for sharing with me!)
The Science of Well Being for Parents from Laurie Santos (Professor of Psychology at Yale)
What are mission-critical habits for you as a working parent? Any routines or strategies that work for you? What parallels do you see between families and startups?
Big events, small events, panels, parties, workouts, virtual — whatever your style, the next few months are packed with potential!
Here are a few that I’ll be hosting or attending.
Can you make it? What type of events are your favorite? Do you dislike networking like I do? 😉
Please feel free to add other events you’re excited about in the comments!
📅 Fri, May 16, 6:45a
📅 Wed, June 11, 6:45a (Atlanta Tech Week edition!)
📍Tech Square - Biltmore Ballrooms
We had so much fun in April, we’re doing TWO MORE JOGS!
Huge thank you to Julie Pierre and Katie Begando for hosting. 🙏🙏🙏
Nothing brings people together like suffering, I mean, running! Very friendly, lots of selfie stops and shortcuts, with coffee (and water 🥵) at the end.
📅 Tue, June 10, 9-10:30a
📍Atlanta Tech Village
During the “Buckhead Tuesday” of Atlanta Tech Week, I’ll be kicking off Startup Summer School presenting on my favorite topic — how to build a big-ass business!
We’ll cover things like how to:
choose the right idea
find your first customers
raise the money you need
confidently lead
…even if you don’t have a tech background.
Event is listed here and register for an Atlanta Tech Week day pass to attend.
Let me know if I should look for you!
📅 Mon, June 8 - Fri, June 11
📍All Over Atlanta!
The biggest week of the spring with over 200+ events across the city, powered by Render ATL.
OF COURSE, I’ll be heading to South Downtown, sharing about billion dollar companies (see #2), and joining the Founder Funder Jog (see #1).
Specific events and schedule are being finalized now so check back to get the latest.
📅 Fri, May 16, 1-2p
📍Atlanta Tech Village
Led by the brilliant Jacey Cadet, get *FREE* help on your startup pitch!
Every first and third Friday at Atlanta Tech Village Buckhead.
I heard from an inside source (shhhh…😉) a regular session at Atlanta Tech Village Sylvan will be added soon.
📅 Thu, June 5, 12p
📍Virtual
Join me and fellow Atlanta Ventures partner, A.T. Gimbel, for an informal Q&A sesh.
Common topics include fundraising, product development, how to get early customers, what we look for when investing, and more!
We do these every month so if you can’t make this one, join next time.
📅 Tue, May 20 - Wed, May 21
📍Charlotte, NC
Check out this 2-day capital summit (kicks off next week!) in one of my favorite Southeastern startup cities.
Led by gWen and Innovate Charlotte, there’s a $100,000 pitch prize, fireside chats (including Eric Spett of Scalebound), and alllll the networking for early stage startups and investors.
📅 Wed, Oct 15 - Thu, Oct 16
📍Woodruff Arts Center
MARK YOUR CALENDAR NOW!
Venture Atlanta is the largest venture conference in the Southeast. (Prepare yourself.)
Get your tickets and start planning your happy hour/networking/pitch strategy today.
Insider tip: the Founder Funder Jog and Female Founder dinner were a blast last year!
Did I miss something? Absolutely! I can never capture all that’s going on in this bustling startup world!
Here are some of my favorite event calendars:
And even more — a list of my favorite resources, groups, and tactics for getting a pulse on Atlanta and finding other tech folks.
Please feel free to drop other upcoming events with details and registration links in the comments below! 👇
Why VCs think about canoes during pitch meetings.
Read MoreWant to get into the head of an investor?
(Do. Not. Recommend. I’m here and it’s terrifying. 😂😂😂)
Seriously though, have you ever wondered what investors looking for when they hear a pitch or meet a founder?
Just like when startups hire, every firm has different values and priorities but here are 5 common “green flags” that investors (including Atlanta Ventures!) look for in founders.
Can they sell?
Selling doesn’t mean greasy used car dealer.
It means compelling storytelling and the ability to transfer belief.
(And it’s why tech sales reps make great startup CEOs.)
Can you get others excited about your vision? Will you be able to get customers, investors, and future employees on board?
#PROTIP
If you don’t have a sales background, you can learn! Here are some great sales books and sales thought leaders to get you started.
Do they want to build a billion dollar company???
Even if a founder is secretly happy with a $100M exit (and who’s not? 😂), they’ve got to relentlessly go after a huge market to build even a mid-sized startup.
(Here’s why investors love — and require — startups building in big markets.)
That drive for greatness keeps you going even when shit is hitting the fan and you could make 6 (or 7!) figures working a corporate job.
Yes, it can feel a little delulu when you only have 10 customers.
But the most successful founders were thinking big from Day 1 and making 10x decisions that aligned.
#PROTIP
Talk about your big vision and practice answering downside questions with upside answers.
Startups are hard.
Even for wildly successful startups, it’s a rollercoaster with highs and lows and a decade of grinding.
Do you want to paddle a canoe with this person for the next 10 years?
Will it be a fun, wild adventure? Or a sufferfest with finger-pointing and grumpiness?
What will they be like when the boat capsizes or springs a leak?
It can be hard to articulate but it’s a mix of attitude, values-alignment, and general likeability. Quirkiness is a-okay and expected!
#PROTIP
Canoe Test goes both ways. Founders should be vetting investors too. Do YOU want to be in a canoe with this investor for 10 years????
Can they read the room?
Or are they so maniacally focused on their vision, they don’t notice someone fell asleep and everyone else is confused? 🥴
Self-awareness is the important counterbalance to someone’s vision and ambition.
You need to believe in yourself and not let haters deter you.
But you also have to clued into reality.
It’s going to be hard to pass the Canoe Test without some humility and emotional intelligence!
#PROTIP
Have trouble reading the room? Check out this amazing interview with Vanessa Van Edwards, body language expert, who explains different micro-expressions (and how to be more charismatic).
Last but definitely not least — are they coachable??
Are they open to an investor’s influence? How do they handle constructive feedback?
Do they get defensive and tell you you’re wrong?
Or do they ask follow up questions to understand more deeply?
What got you here won’t get you there, so a founder’s ability to learn and grow is one of the most important leading indicators of a company’s success.
Growth happens when you seek out feedback and listen judiciously to those around you.
Investors don’t expect founders to be puppets. OF COURSE, founders will take the inputs and do what they think is best. But if a founder is never open to feedback, it will be a frustrating (and short) canoe trip!
#PROTIP
Tons of resources to facilitate personal growth — here are strategies used by top founders and a primer on finding an executive coach.
Like anything in Startupland…there’s exceptions!
Every investor is different.
We have different personalities and life experiences.
Investment firms, like startups, are a reflection of their founder, thus the culture and strategy can vary significantly between firms.
Good news/bad news — there’s no single playbook for success!
Investors, do you agree? What “green flags” do you look for?
Founders, what do you look for in an investor??
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Most startups measure the wrong thing. Here's how to fix it, starting today!
Read MoreI was focused on the wrong metrics for a decade.
Like most startups, we religiously tracked subscription revenue, renewal rates, # of customers, average deal size, plus alllll the product usage.
Does this sound familiar?
How well are they using the product??
How many users?
How often are they logging in?
How many in-app actions are they taking?
Do they like our product?
How many support tickets do they submit?
Let’s set up alerts for customers not using the product so we can reach out!
These are all good ideas. You do want to track these to measure the health of your business.
But they miss the most important point.
Which will be SO OBVIOUS after you hear it.
That’s how I felt when Francis Cordon opened my eyes to what really matters…
Here’s the most important thing to measure related to customer success (and ultimately the overall health of your business).
It’s not how much are they like or use your product.
It’s things like:
Are you making your customers better at their jobs?
What mission-critical business metric are you improving for your customer?
What does your customer get measured on?
While I was busy tracking how many emails customers sent, the customers were looking at how much revenue they created for the business.
We could even track revenue generation in our product — but that wasn’t the metric we looked at to understand customer success! 🤦♀️
Quick and dirty examples to get the wheels turning.
Marketing software → are your marketing power users generating revenue?
Faster website software → do you have more online sales?
Financial management software → is your net worth/income/saving growing? do you sleep better at night? 😉
Vertical CRM software → are revenue/profits growing?
You’ll see that it’s rarely about “efficiency” and it’s never about the functionality of the product. Yes, your product does cool automation. Users don’t care. (I know! I’m sorry!!! I love your product baby too!!) They care how your product helps them achieve something even more important that “good product adoption.” 😉
Happy to brainstorm for your business if you’re stuck. Just shoot me a note!
Save yourself a decade.
Start now aligning everyone in the company to the metric that customers care about.
Not the in-product or revenue-related proxy metric that your company cares about.
Ideally, you want to show this North Star metric to your customer in the product.
If you’re not there yet, start leveraging Customer Win Slides asap (a good idea anyway!).
I’ve never heard from a single company who didn’t have great results from Customer Win Slides.
Yes, you still need to think about pricing and go-to-market strategy and build a good product and all those things.
But at the core, if you are helping your customer be better at the thing they truly care about, you will have a great business!
P.S. Want more customer success advice, lessons, and templates? Check out the complete guide.
What do you wish you learned 10 years ago? What startup lesson seemed so obvious in hindsight? What do you measure to track your customer’s (true!) success?
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How do you build a billion dollar company? Bring a lot of energy and momentum for days, weeks, and years. Here's how.
Read MoreHow do you build a billion dollar company?
One day at a time.
Over 10 years.
That’s 3,650 days. (3,653 if you’re counting leap years!)
How do you last that long and have energy to tackle every day?
❌ NO: Spend 10 years grinding — sitting at a desk, in a dark room, staring at a screen.
❌ NO: Do “healthy” things that feel like another job.
❌ NO: Sacrifice your physical and mental well-being and burn out after a few years.
✅ YES: Do things you enjoy along the way that bring you health and momentum!
Here’s 4 ways to maintain a healthy lifestyle as a founder — while still having fun along the way!
Cross-my-heart-hope-to-die-stick-a-needle-in-my-eye, I PROMISE, you can find healthy foods that you like.
Contrary to popular belief, I don’t sit around eating raw broccoli for every meal.
BLECH.
I put olive oil and salt on that broccoli and roast the heck out of it!
Show me an adult who can’t find a roasted vegetable they like, and I’ll show you Warren Buffett or Donald Trump.
(That was a fast food joke, not a political one, okay, people?? Those two are notorious fast food lovers.)
Here are some of my favorite quick, nutritious lunches, healthy fast food options, and easy recipes.
Hate everything mentioned there?
That’s cool.
Tell ChatGPT what foods you like and ask for healthy recipes that can be made in 20 minutes or less. “Healthy” can be defined as certain carb/fat/protein splits or calorie count or however you want to be eating.
AI is my favorite meal planner!
I love my Whoop.
Every morning I get a score!
Hellooooo, dopamine hit.
(And it’s related to health instead of social media metrics! 😅)
Oura ring, Apple Watch, Garmin, Fitbit, Reframe App, step counter…there’s 100 ways to turn health into a game!
If a tracker doesn’t do it for you, how about joining Atlanta Ventures for our (very unofficial, is-it-even-happening) six-pack challenge?
Here’s the game (as borrowed from the genius/sadist Shawn Tucker):
6 months to get “6 pack” abdominals or you pay everyone else who is participating $1000.
Now, none of us really have $1000 sitting around which means…SIX PACK OR ELSE!
(Comment below to join the “fun” 😂)
Okay, if trackers and peer pressure don’t sound like games to you, here’s one more option: play an actual game.
Tennis, pickleball, kickball, basketball, soccer, squash, frisbee, gung fu, and thousands more.
Social connection is really important.
Social connection outside of your startup is really, really important.
Do something healthy and make it social:
Play a game with friends.
Eat healthy food with friends.
Join a sports league or training facility.
Sign up for a race and train with a group.
Become friends with people who like healthy things.
Go on an organized outdoor adventure trip.
Come to a Founder Funder Jog - duuuuuuuh!
Yeah, it’s not rocket science. But neither are startups. (Well, unless they are.)
Doing things with friends gives you accountability, makes it more fun, and fills your emotional cup!
Everyone has a few things that make or break their well-being. They are different for everyone.
I’d like to get something off my chest:
Meditating stresses me out and I never do it.
Yes, yes, I know it’s good for me. I’m doing it wrong. I need to practice. Blah blah blah.
It’s not my thing.
Getting a good night’s sleep…now THAT’S my thing. All grumpy days can be directly correlated to me sleeping poorly.
So, here’s the question — what are your personal keys to success that help you have a great day, feel good, and bring the energy?
If you don’t know, it’s a good reason to test things out. Here’s how I like to test things!
Here’s a few categories to trigger ideas. Within each are sub-categories, e.g. try out different types of exercise.
Exercise
Morning sunlight
Sleep
Meditation/Prayer
Certain foods or supplements
Schedule/Calendar
If you’re looking for ideas, here’s a few things that work for me:
Standing desk with walking pad (if you’ve seen me on Zoom, you know…)
Red Light (s/o Kathryn Farrell!)
Less alcohol (use Reframe to cut back and try my fave non-alcoholic beer)
Walk my kids to school (sunshine, fresh air, exercise, family time)
(NOTE: I added these slowly over time! Don’t try everything at once. 😂)
Want more?? Check out the The Entrepreneur’s Survival Guide to Staying Healthy!
What are some of your favorite ways to make healthy habits fun? What worked for you? What’s the most fun healthy thing you do??
Brilliant founder getting in their own way? Try these 3 things today.
Read MoreI recently spoke to someone working with a brilliant founder who was getting in their own way.
The founder wasn’t open to new ideas or different perspectives and it was hurting the company.
How do you reach someone who won’t listen or shuts down other people’s suggestions????
Replace “founder” with “boss,” “co-worker,” “my teenager.”
Or maybe instead of reporting to the founder, you are an investor (hypothetically speaking of course) who can’t “tell” someone what to do but wants gently steer in a positive direction.
Here are 3 strategies I’ve found helpful when working with strong-willed founders (or anyone!) — as a startup COO, tech investor, and general human being.
You almost never change someone's mind by telling them what to do.
But you can change someone's mind by asking them thoughtful questions so they realize what to do.
And think it's their idea.
There's a reason why therapists (and business coaches!) ask questions.
And it's not because they don't know the answer. 😉
Having someone else come up with the answer, say it in their own words, feel ownership, use their own wisdom — is wildly important for buy-in and change.
Furthermore, it’s possible that you don’t have the exact right answer. Maybe you don’t fully understand the situation or maybe they have an even better idea than what you’re thinking of.
Asking questions can uncover all sorts of brilliant solutions!
You know what the title of this section should have been???
What happens if you ask more questions?
What are good questions to ask?
What helps change your mind?
See how much more fun questions are than directives???!!!!!
Did it trigger any great ideas?? 😉
If you know me, you've probably heard me suggest this before:
"Can you do it as a test?"
Yes, of course, at Atlanta Ventures, we love to run tests around business ideas (examples here and here).
It works for internal projects as well!
If you have a new idea or you’re hitting a lot of objections, instead of trying to change everyone’s mind, suggest an experiment.
“What if we try [XYZ] for [30] days? I could run a quick test doing [ABC] for [$1000] with the goal of [123].”
Designate a specific amount of time, money, resources, and what a successful outcome would be. Here’s a step-by-step process and template and a description of SMART goals.
It’s low risk for the business and — very important — the ego!
No one is directly challenged, no one is “wrong,” no one has to communicate a change in strategy.
It’s a low-key, short-term experiment with clear parameters.
Who doesn’t love to try new things and look at the results?
A brilliant HR leader (hi Carey Bongard!) taught me this one…
Whenever possible, phrase feedback or coaching as “more”:
Why are we pouring money into that dumpster fire? Let’s do more of what’s working well.
Be less negative. Can you give even more positive feedback?
Don’t focus on the details. Do more strategic, big picture work.
You’re not communicating enough. Communicate more across the company.
You are going rogue and it’s causing problems. More collaboration with the engineering team.
Humans are much better at doing more of something than less.
Feels abundant, expansive, and positive.
Especially good for someone who:
reacts poorly to constructive feedback
you want to influence and inspire in a positive way
is your boss 😉
Do more “more”!
Spoiler Alert: these strategies work on direct reports, anyone in your organization, even family members.
In a shocking turn of events, most people don't like being bossed around and aren’t going to do what you say even when you’re right!
(I know. It was a terrible realization for me too. The world would be so much better if everyone just did what I say!!! 😜)
I should also be clear that there is a HUGE upside to that annoying stubbornness you’re dealing with.
It means someone has high conviction, they don’t give up easily, and they’re not swayed by others or peer pressure.
When dealing with humans, it’s always a mix of good, bad, and messy!
Just like a startup. 😉
Have you used any of these strategies? Do you have other tips for helping to shift a stubborn individual? Founders, have you ever been hard to convince?? 😁😉🙋♀️
I’d love to help more entrepreneurs! If you’re enjoying the O’Daily, please share with a founder or startup leader who would enjoy practical tips and #momjokes. 😁😁😁
A lot of U.S. families head out on Spring Break this month.
Which makes it a great time to reshare my favorite quote from founder and investor, Alex Friedman!!
Idk who needs this but I’ve seen a few startups fail because of founder burn out. I haven’t seen any startups fail because a founder took a couple days off.
I’d even go so far as to say, often the biggest business “ah-ha” moments happen when you’re away from the day-to-day grind — even if it’s 24 or 48 hours!
One of my other favorite quotes is from Tim Ferris:
What one thing, if done, could render all other things irrelevant?
It’s hard to see clearly when you’re in the weeds. Everything is urgent and important. You’re just trying to get through your inbox, Slack, and meetings.
With a bit of space, all the sudden you realize:
a customer insight that’s been staring you in the face
things in your schedule that don’t make sense
the industry you need to start looking at
problematic customers you need to fire
the mission critical senior leader to bring on
which sales strategies are working
what KPIs matter the most
and a million other things that are obvious as soon as your subconscious takes over!
Give yourself and your company extra fire power this month — by taking time away.
Do it right now. Block a whole day on your calendar. Plan a camping trip. Have a friend “force” you to do something fun for a weekend. Leave your phone at home.
Your soul — and your business — will be better for it.
(Pass this along to a founder who needs the reminder!)
Any fun stories about a great business “unlock” that happened when you took time off? I’d love to hear them (or share them below)!
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