75 quotes from 60 pages of notes from 25 meetings from 18 people from 10 weeks of Techstars Chicago.

I would often run out of space.

“Early enough, you need part of your idea to be a bad idea. If enough people think it’s a good idea but you’re not scaling fast or you’re not pointy in your message, you’re fucked. Someone else will come along and do it faster or pointier. Have something worth taking a risk on.” -Logan LaHive


I tried my best to carry my notebook with me to every meeting and every session that I was able to attend. (And my friend Rachael made sure I went to every session I was in the building for) I’m now flipping back through those pages and pulling out the quotes that slapped me across the face.

I also tried my best to preserve their words, but I may be paraphrasing a bit to encapsulate the thought.


Logan LaHive gets more quotes than anyone. He is equal parts patient and challenging. I trust his advice.

“Startups fail because the founders split up or they run out of cash.” -Logan LaHive
“Running out of money for a company is like running out of breath for a human. Sub-optimal.” -Logan LaHive
“You can’t cut yourself to growth.” -Logan LaHive
“If what you’re working on doesn’t directly relate to your KPIs, avoid it.” -Logan LaHive
“Don’t make internal changes [relating to budget and personnel] until existing conditions become intolerable.” -Logan LaHive
“Missions can change. Goals can change. Values don’t change.” -Logan LaHive
“I don’t do anything in the middle. The middle is a very uncomfortable and dangerous place to be.” -Logan LaHive
“Operate with intent. Make decisions and keep moving.” -Logan LaHive
“Time kills all deals. Momentum is everything. Use it to move deals forward.” -Logan LaHive

Mayur Gupta dropped by to talk candidly about Spotify and growth and culture.

“The burden of growth belongs to everyone in the organization.” -Mayur Gupta
“Find your core audience and build the product only for them. Figure out how they retain before you figure out acquisition.” -Mayur Gupta

Jeff Martin went through a really great activity with each company in the cohort where we had to write down our 3-year plan, 1-year vision, and Quarterly imperatives.

“If you have somewhere to go, you aren’t just going to get in a car and start driving. Likewise, if you have goals as a business, you need to create a plan to accomplish those goals.” -Jeff Martin
“Discipline equals freedom.” -Jeff Martin

Mike Evans talked to us about building a team.

“Disclose your runway to your potential hires. You owe them the right to know what their risk is.” -Mike Evans
“Always hire from zero to one. Never hire from zero people in a role to two people in a role. That first person will always help you figure out what you need from (or if you need at all,) a second person.” -Mike Evans
“For every full time employee you add, all your other people lose a bit of productivity. Be careful when you scale.” -Mike Evans
“Hiring is a funnel, and you need to focus on the top of the funnel. Get as many applicants as possible at the top of the funnel, and work your way down. Diversity happens at the top of the funnel.” -Mike Evans

Alida Miranda-Wolff also spoke to us about hiring, but mostly about building culture.

“Anything under 30 employees is a ‘family’ stage. Over 30 employees is ‘organization’ stage.” -Alida Miranda-Wolff
“Culture happens when a group comes together to agree on ‘a way.’ That is exhibited by activities, behaviors, and institutions.” -Alida Miranda-Wolff
“Hire people who are self-aware, self-motivated, and willing to steer their own growth.” -Alida Miranda-Wolff
“Hire for values. Competency changes, values don’t.” -Alida Miranda-Wolff
“Employees want coaching, a clear career path, community, and good pay.” -Alida Miranda-Wolff

Amanda Lannert came in and chatted with us about her story. She was poised, delightful, and candid; a skilled storyteller and savvy professional.

“Be helpful. If nothing else, be helpful.” -Amanda Lannert
“It matters more what a leader does than what a leader says.” -Amanda Lannert
“Interviewing is like a blind date without the drinking.” -Amanda Lannert
“If you can, be choosy about your investor. A bad/slow/risk-adverse investor can be the biggest waste of time.” -Amanda Lannert

Holy shit, Mike Rome is awesome. He talked to us about growth and it was all super practical.

“Embrace a not-to-do list.” -Mike Rome
“Activate first, educate later.” -Mike Rome
“Everyone in the company is on the growth team. If not, then you’re not dedicated to grow. If you’re not dedicated to grow, you aren’t a startup.” -Mike Rome
“Collect ideas. While it’s hard to know the best ideas, it’s usually easy to eliminate the bad ones. So it’s still very beneficial for experiment success rates.” -Mike Rome
“Find the minimum viable test.” -Mike Rome

Troy Henikoff (the papa bear of Techstars Chicago) was incredibly generous with his attention and wisdom. He spent a lot of one-on-one time with every company in the cohort.

“Find the early indicator that proves that cohort of users will stay. Spend money to get more of them.” -Troy Henikoff
“Have a hypothesis. Assume true until proven false.” -Troy Henikoff
“Everything you do should be a two-fer: move forward AND learn.” -Troy Henikoff

Stu Grubbs met with us in his office at Lightstream and gave some really great feedback on how to operate as a team.

“Over-do the verbal communication.” -Stu Grubbs
“Retreat [time off] is something that is wildly undervalued.” -Stu Grubbs
“The CEO’s job is to look 6–12 months down the road. Stand at the helm of the ship and look for waves.” -Stu Grubbs
“At a certain point you have to tell everyone to shut the fuck up. Listen, distill, and then get to work. Do it, and stick to it.” -Stu Grubbs

Amish Desai was a wealth of one-liners and nuggets. I could open up a fortune cookie company of just Amish Desai quotes about customer engagement and loveability. But, I’ll keep it to a max of 5 because that’s my promise.

“What is your minimum lovable product?” -Amish Desai
“What is the emotion you want to activate at each interaction? Design for that emotion.” -Amish Desai
“Get weird and try things. Fail fast, and be rough and ready. You get points for doing it.” -Amish Desai
“Take risks on the delightful experiences, and then test them.” -Amish Desai
“Your users’ last best experience is your competition. Be more delightful than their last delightful experience.” -Amish Desai

Matt Matros from Limitless Coffee stopped by to tell his story. He balanced helpfulness with humility with candor with generosity. Really earned my trust. Imma cheat and put 6 quotes here.

“You’re always the best in the world at something.” -Matt Matros
“Your business is not for everyone. You have to be okay with that.” -Matt Matros
“Panic can be a good motivator.” -Matt Matros
“Founders raise money on the future. Investors invest on the past.” -Matt Matros
“It’s not about the story you tell, it’s about who cares about that story that matters.” -Matt Matros
“It’s always easier to accentuate your strengths than to try to fix your weaknesses.” -Matt Matros

Okay, for real, Rachel Fukaya is one of my favorite people. And meeting her was a true highlight of my time at Techstars and in Chicago. She sat down with us and helped us through a lot of Kai-specific language. So the notes I have on her notebook page are not universal (even though there is a little heart drawn next to her name), but I would be remiss if I didn’t mention her.


Dylan Richard has a little note scrawled next to his name in my notebook. It reads, “He’s so wise.” And it’s true. And while most of his notes are also very application-specific to our business’ challenges at the time, he made it clear that there are a hundred ways to get there. That notion really helped our team think bigger and broader about the business.

“You don’t need to get to product/market fit right as much as you need to get to your core message.” -Dylan Richard

Chris Davis came in to talk about Active Campaign, and brought up some really practical tips for middle-of-the-funnel acquisition, most specifically for B2B.

“Know as much about the user as possible before making an offer. Glean info from their behavior.” -Chris Davis
“Onboarding is why they stay. Give them quick wins so they feel invested faster.” -Chris Davis
“The job of marketing is sending your sales team the best information as possible.” -Chris Davis

Lauren Funk from Tovala came in to talk about content.

“Content is the art of publishing. If you’re going to dedicate to content marketing, you have to act like a publisher. That means having a plan.” -Lauren Funk
“Content is the overlap between product, marketing, and sales.” -Lauren Funk
“Get early stories from your best users and use those results as value props.” -Lauren Funk

Stella Garber came in to chat about social media marketing and I was a total fanboy.

“Social media is NOT a community. It’s a channel. Don’t get the two confused.” -Stella Garber
“Social is not scalable and you can’t control it. If it works, it works really well.” -Stella Garber
“It’s simple: Just be really fucking good.” -Stella Garber

Gregg Latterman dropped by and told amazing stories about his time at Aware Records.

“[When hiring,] identify hustle. Find people that are smart enough, but not coddled.” -Gregg Latterman
“If you’re going to take money, take money for growth.” -Gregg Latterman
“If you get to where you’re heading, will that be where you want to be?” -Gregg Latterman

Casey Winters. I had seen a version of this talk before from a 500 Startups recording from batch 17 while I was working for Cladwell, but HOLY BUCKETS. I took some notes with this, and had to raise my hand about 10 minutes in asking if he would share his deck because I couldn’t write fast enough.

“Look at your retention curve. If the curve flattens, you have product/market fit for that cohort of users. Can you grow with that?” -Casey Winters
“If you can’t detect a difference when testing, it didn’t work.” -Casey Winters
“Experiments should be designed around what you can learn, not what result you want. Experiment velocity alone will equate success.” -Casey Winters
“The teams that win are the teams that move the fastest. You should be moving so fast that your early designs are shockingly bad.” -Casey Winters
“Eliminate friction in your onboarding process to get into the experience quickly. Then, create friction in your product to get people to the ‘ah ha’ moment.” -Casey Winters
“You are not your customer.” -Casey Winters
“The only users that really matter are the new users. But don’t piss off your current users.” -Casey Winters

Oh god, there’s so many more.


Harper Reed. What a maniac. I love this guy. Just google “Harper Reed” and soak in it.

“You’re a founder. You don’t know anything. You just have the hubris to say you are the only one who can solve this problem. You need to surround yourself with people who will build it while you stand up on a mountain, yelling.” -Harper Reed
“Imposter syndrome is real and it never goes away.” -Harper Reed
“Remember the things you didn’t think you could do so you can convince yourself that you can do what’s next.” -Harper Reed
“If doors close, don’t limit yourself to doors. Go through a window.” -Harper Reed

“You don’t know what you’re capable of doing.” -Harper Reed


Techstars Chicago was a life-altering experience. I learned more in the past 10 weeks than I have in the past 5 years. I’ve been able to be around some of the smartest people I know about, and watch 10 companies grow by leaps and bounds. Thanks, Logan and Rachael, and the entire Techstars world. I’m in love.