20VC Newsletter - Dec 10th, 2023
Top takeaways from 20VC episodes released this last week!
Monday’s episode with Tooey Courtemanche, CEO of Procore Technologies:
Download the trasncript here:
Harry’s Top 10 Takeaways:
1. Up and To The Right is Total BS:
We had to go without a paycheck.
I had 2 mortgages on my house.
I had sold my car.
My wife looked at me and said, “I believe in this vision as much as you do”.
2. Will the market remain irrational longer than your company can stay solvent?
Between 2002 and 2015, we'd grown revenue from $0 to $9.6 million.
8 years later, we hit $890M.
We did not do anything different in 2015, the market change to our way of thinking.
3. How to Approach Market Timing Risk:
The more things that have to happen in order for a company to be successful, the higher the risk ratio is.
4. Smart and Hungry is not Enough:
I've hired a lot of hungry and smart people.
They tend to be assholes and not be good team players.
They tank culture. Get rid of them fast.
5. When Culture is No Longer the Role of the CEO:
When you hire, smart, hungry and humble people, they start to self-regulate the culture.
One you get this solid culture, the CEO is no longer the culture keeper.
Organ rejection kicks in and the culture bar is in place.
6. Advice from Tobi at Shopify on CEOship:
If your business is scaling at 100% a year, that means you and your team needs to be scaling their skill set at greater than 100% a year.
7. The Piece of Advice that Changed a Billionaire’s Life:
I was once given advice by a Professor I think to everyday, they said:
“When you have five minutes like you do right now, do a five minute job, tackle something.”
8. Why the Idea of “Becoming an Entrepreneur is BS”:
“Becoming an entrepreneur” is not a thing. You don't become an entrepreneur.
You follow a passion and you solve a problem for a customer and you build a business.
Instagram vs reality of being a CEO is different.
9. Why Being a Great Leader is Like Parenting:
If my child skinned his knee, I would not mollycuddle him. They need to learn.
Same with teams; you want people to learn from their mistakes. You want to teach them without doing their job for them.
10. What a $BN CEO Wishes He Had Known About Leadership:
At the beginning, you do everything. At a point, you no longer should do that and start leading.
You have to let go of doing actual work & empower people.
You have to trust that they can do the job better than you.
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Wednesday’s episode with Geoff Charles, VP Product at Ramp:
Download the transcript here:
Harry’s Top 7 Lessons:
1. Hire People with Stage not Sector Experience.
If you hire someone from a larger company, they have often not actually done the work for a long time.
Hire more scrappy people who have gotten their hands dirty more recently, even if they come from a different space.
2. What the Best Product Teams Do Early On:
They sit with sales, they need to sit on every sales demo.
They act like professional services teams. Find one or two design partners and just build for them.
They will love you more than any best in class SaaS product.
3. How to Get Clients Who Have Hard Switching Costs:
We were aggressive.
We would sit down with clients and say, give me your old credit cards. Log in to all their other software and switch cards for you.
Give them no reason to say no, be relentless.
4. How To Structure Two Week Sprints:
Monday: Leads meeting; discuss plan for next two weeks.
Tuesday: Team-wide scrum meeting; 5 to 10 people, this is what we're doing.
No other meetings that are recurring in the product development process.
5. The CEO Does not Need to be the Head of Product:
They need to be able to opine on what looks good and what doesn't.
Good decision vs bad decision.
But you need to have an empowered product team and tech team that actually calls the shots in terms of the sequencing.
6. Biggest Advice to New Product Leaders:
Over-communicate.
Give weekly updates.
Decisions made. Trade-offs made.
Always over-communicate, you will build trust.
7. How To Be Efficient When Building a 2nd Product:
Ask yourself, what building blocks from the first product can I reuse to make the second product?
You should go after a second product that has economies of scale in terms of systems you've already built.
Reusability is key.
Friday’s episode with Sanjit Biswas, CEO of Samsara:
Download the transcript here:
Here are the top 7 takeaways:
Product-Market Fit: Biswas emphasizes the natural evolution of product-market fit rather than forcing it, advocating for creating products that elicit "wow" reactions from customers, indicating a genuine need.
Market-First Approach: He highlights prioritizing market needs over technology, suggesting that successful businesses identify and cater to existing market demands rather than pushing technology solutions searching for a problem.
Founder-Led Sales: Biswas discusses the advantages of founders directly engaging in sales, including better understanding customer needs and receiving direct feedback, which can guide product development.
Customer Engagement in Product Development: Direct interaction with customers is crucial for product refinement, as it allows for real-world feedback and ensures the product addresses actual user needs.
Scaling a Business: Biswas talks about the challenges in transitioning from a startup to a scalable business, emphasizing the need for adaptability and strategic planning in growth phases.
Flexible/Hybrid Workforce: The discussion includes the benefits and challenges of a hybrid work model, such as increased flexibility and the necessity to maintain company culture and communication.
Capital Allocation and Investment: The importance of wise capital allocation for long-term business growth is stressed, underscoring the need for strategic investments in areas that yield long-term benefits.
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