At
@Instacart
, I had the privilege of being part of $2.4 billion in equity capital financings over eight years.
We raised money in various market environments – sometimes with great metrics and many times with terrible performance but a great story.
We worked with firms across
Getting a Deal vs. Losing the Perfect Deal
At
@Instacart
, we excelled at signing enterprise customers by being clear on our 1-2 non-negotiables across all deals and flexible on the 100’s of other deal points that could come up in any individual negotiation.
We treated every
**Announcement: I’m starting a blog, Captain, Crew, & Capital, to share what I have learned from being a technology entrepreneur, builder, and investor for the last decade.**
“We will be cash flow profitable this year for the first time since the company started in 2005. I guess
A bad day for 🇨🇦's innovation sector. Representative texts from investors/friends:
- "I am worried Canada is going to be a bad regime for your new company"
- "Crazy stuff coming out of Ottawa! Will this hurt hiring?"
-"This tax thing seems bad"
One of the things that has been scariest for me in building a new company is the weight of expectations.
Because
@Instacart
was a success, I felt the bar for success to be naturally higher.
As a result of this insecurity and my observations about how the companies I most admire
10 principles for building a founding team:
1. Know thyself.
I used to think it was trite when people talked about “doing the work” to understand yourself. But I’ve realized how crucial it is, especially in team building.
You need to be crystal clear on your working style,
Leaving the week optimistic about 🇨🇦 tech - met with over a dozen amazing candidates
Founders have an embarrassment of riches with access to Canada's real natural resource - smart/hungry/ humble people who want to build
@gokulr
Thanks for sharing
@gokulr
Hopefully we start seeing a lot more of this
Good way for founders, investors, and employees to manage the tug-of-war tensions around liquidity vs building for the long-term
Building a new company, I find myself faced with opportunities to revisit and modify Beacon Software’s strategy much more than I would have expected.
Some of this is due to the nature of Beacon’s business, but I think it is natural in the early stages of company building.
The importance of speed in building:
We recognize that sprinters are the fastest when they get out of the blocks, and the winners in a sprint slow down the least.
(An excerpt from my recent blog post: Getting Out of the Blocks Fast.)
I've found this with the best sales leaders as well
They deeply understand their clients and are expert at monitoring real-time reactions from 'customers' (who invariably become friends) while in conversation
They throw out what doesn't land and are always honing their message
The single best fundraisers are like comedians.
They test a message. Measure the response from the audience and iterate. See what works, keep that. See what does not, discard that.
Constantly measure, iterate and improve. It is a game of A/B testing.
Reminded of this Munger quote today for no particular reason…
“if the elite campuses were as successful as McDonald’s in teaching sensibly, we would have a better world”
There are 2 types of cultures and 2 types of people. Build & hire wisely.
Principal cultures/ppl:
- Forever horizon
- Relationships = B/S asset
- Everyone's an owner
Agent cultures/ppl:
- Short-termism
- 0 sum txn's
- Everyone's trying to get their 💰
Principal Agent Theory
If I own a business and I do everything myself, I should expect to act in my own best interest. As soon as I start delegating, I introduce agents. People are doing work on my behalf. They do not always have or act in my best interests. The difference
"Business is actually about finding problems, embracing and even enjoying them — because each problem is an opportunity to remove an obstacle and get closer to success.”
Building a new company which gives me the gift of meeting dozens of real world entrepreneurs every week, I am
Learned a forever lesson from
@ROWGHANI
during
@Instacart
’s PAINFUL series D:
- List everyone you work with who you provide value to
- Find a win/win way to get them to fund you
Build a company that is “too important to fail” to your partners and you’ll always have capital
When fundraising you will get many No’s and many poor excuses.
You cannot let it affect you. You cannot take it personally.
Get up and get out there. This is a numbers game, do not stop. 🔥
A subtle change which has transformed my daily mood is being deliberate about skewing to optimistic conversations/information first thing in the morning
The media you consume and people you interact with in the first 60-min of the day sets the lens with which you view your day
The only thing a life coach can teach you is how to be a life coach.
The only thing an influencer can teach you is how to be an influencer.
Be as careful of the information you ingest as the food you eat. You wouldn't eat random food from someone, stop ingesting their ideas.
“The only thing that can stop Instacart is when this group of people (pointing to the group assembled in the living room of 41 South Park) stops liking each other.” – Sir Michael Moritz
Last summer, after wrapping up my time at D1, I knew I was ready to build again.
But before
I often wonder what the importance of "speed in building" actually means in practice.
Here’s my attempt to answer that question:
1. Finding what to compromise on.
Moving quickly at the start of a company, when you don’t yet understand the market and have only the shell of a
"No one is hiring right now"
Every employer has an infinite budget to hire folks that they perceive will add significant value to their organization. Either bring in a ton of revenue or save them a lot in costs.
This is especially true of small to medium size employers.
An unexpected byproduct of integrating more AI tools in my daily workflows …. I am working MORE
Knowledge workers use AI to improve the ratio of impactful-to-monotonous minutes in a day
AI feeds a curiosity to keep turning over more/new rocks = longer but better workdays
@ReamBraden
More than anything else - we need to normalize and reward ambition.
Canadian humility often gets confused with a lack of global aspirations.
Canada has been responsible for an incredible amount of innovation per capita - from insulin to Shopify!
When I meet Canadian
“Companies - just like gangs, armies, and nations - are large organizations that rise or fall because of the daily micro behaviors of the human beings that compose them“ -
@bhorowitz
The best (and hardest) thing about building a newco is starting from scratch on culture.
@patrick_oshag
Incredible content density for investors, board members and founders
My favorite takeaways:
- Investors: Deals are not zero sum
- Board Members: Avoid "I'm the board member from" syndrome
- Founders: People want a piece of you, remember the 'theory of the note'
My conversation with Frank Blake on leadership
I’ve asked around a lot looking for leaders who did their thing quietly and generated great respect.
Frank’s name came up A LOT
This is worth a listen if you are in charge of anything involving other people
So many great lessons
@harleyf
@skanwar
💯 - leaving is giving up
As 🇨🇦’s our relationship with our country shouldn’t be about “what have you done for me lately?”
Transactional relationships and short-termism don’t build great companies or great country’s
I’m excited about a community of builders figuring this out
🇨🇦 This is the metric and trend line that matters when measuring long-term health of a nation
Just as companies care about market share, countries should care about GDP share
This is the best graph I could find for 🇨🇦… has anyone seen any better data?
Congrats to the GOAT board member
@jeff_jordan
on his retirement from the
@Instacart
board!
Thank you for everything - I learned so much from you over the years and am eternally grateful 🙏🏽
@pmmckinlay
@oliviachow
IMHO it is less about the breadth of our public transit network or the # of subway lines we have
Sadly people are choosing to drive into the downtown core (despite that becoming increasingly expensive) due to personal safety concerns while using the subway/street cars
1/5 Watching this clip made me sad. Sad because as a Canadian it rang true. Sad because we have gone from being the envy of the world to the well deserved butt-of-it’s jokes.
@harleyf
💯
@harleyf
! I woke up this morning dejected - but as the day has progressed I have become optimistic that this is just another problem to solve
I don't know the answer... but I do know 🇨🇦 entrepreneurs like you know how to innovate to solve problems like no one else ... LFG
+1 to this great advice from
@fidjissimo
- you are the rare leader who was able to do both!
Doing an enormous volume of work and creating immense value from your high quality ideas.
One of the things I love most about company building is you are forced to do both simultaneously
People gain so much seniority once they move from a mindset of creating value primarily through the volume of their work to creating value primarily through the quality of their ideas. It doesn’t mean working less; it means directing one’s efforts towards quality over quantity.
Things I have noticed with great candidates recently:
1) Asked L3 & L4 questions and were not satisfied with surface responses
2) Went down research rabbit holes, consumed bespoke media and used novel data sources
3) Able to argue both sides of an issue equally well
What are some signs a person is high IQ - what are some “hard to fake” signs where you can look at someone and say “probably a member of a group that is higher IQ than average?”
Recently, after a board meeting and a series of investor discussions, I found myself pushed to be more ambitious.
This feedback prompted me to reflect on my journey at Instacart and to think about what I have seen in terms of timing a big swing.
“Leaders are paid to make a few
@ataussig
🇨🇦🙏 - you are too kind my friend
The best and highest use for builders is to build enduring companies in Canada
Excited to be building Beacon as a Canadian company!
Dynamic at (small) software co's who benefitted from the pandemic:
- COVID tailwinds scrambled normal growth motions
- Good co's kept effort/intensity high
- Bad co's mistook good outcomes (growth) for good process (strong prod./GTM)
Showing up in 2024 win and retention rates
Great point
@allenlau
. The capital gains changes are a symptom of a more corrosive root cause - institutions which are unfriendly to ambition, growth and productivity
Celebrating entrepreneurship, rewarding innovation, and welcoming competition is how we can turn this around
@billsmitha
So cool to hear this origin story
@billsmitha
. This helps explain why you were such a formidable competitor at Shipt! Congrats on
@HelloLanding
. Love to see builders following their intuition and bringing new things to life
@HEB
is an absolute juggernaut. Not only one of the best grocers in the world, one of the best company’s in the world. All while staying private with a Texas style humility combined with Texas sized ambition. I am blessed to have learned from them as a partner.
Postcard - Texas stopover…
‘H-E-B is the first grocery retailer to be recognized three times as number one in the RPI ranking after a nationwide study that examined the circa $1 trillion U.S. grocery market.’