Riding a Rocket Rocketshipjobs.com

Interview with Doug Ludlow of Mainstreet

On this episode we talk to Matt about his time at Venmo. Going through two acquisitions, competing against Cash App, how he would make Venmo better today and much more!

3:00 - What made you decide to join Venmo?
5:55 - What was the hiring process like at Venmo?
7:45 - What was it like being at Venmo when they were being purchased by Braintree?
10:45 - How did being acquired by Braintree effect your equity?
12:05 - How was it like being acquired by Ebay?
19:00- What do you think makes someone successful at a startup?
21:24 - Why do you like working at a startup?
23:40 - How big was Stash when Matt left?
27:20 - What was it like when CashApp came out
30:00 - What would you add to venoms social feed if you were still involved with the product?
34:35 - What is Stash?
36:30 - why did you leave stash?
38:00 - what is novo and why did you go?
44:00 - How does Novo make money?
47:30 - How large is Novo?
48:30 - What position are you hiring for today?

In this episode we talk to Peter Caputa about how he went from struggling entrepreneur to Hubspot VP to CEO of a multimillion dollar ARR business!

2:00 - Why did you decide to join hubspot?
4:45 - The reason you joined hubspot was because of the financial benefit or something else?
6:27 - What started your idea of creating the hubspot partner program?
10:45 - Why did he continue to push hubspot partner program after being told no so many times?
12:00 - How old were you when you were creating hubspot partner program?
13:20 - What are the characteristics of someone who is successful at a start up?
15:00 - Do you think joining a start up is the right way to get rich? Or why should people join a startup?
16:20 - How to see a rocketship company
18:00 - How did you negotiate for more equity over time?
19:11 - How Pete won 50,000 shares of hubspot stock
23:15 - How do you view the long term goal of Databox?
26:51 - What was the ARR when you joined Databox?
- few thousand dollars.
- 1.1M in july 2018
- jan 2019 1.7M
- 2.8M Arr
- check blog post called how to manage performance during crisis
28:00 - How COVID-19 has effected Databox.
32:00- How to make your SEO better using Databox
34:00 - Why did he choose the go to market strategy that he chose for Databox
41:00 - Does Databox have direct sales reps?
43:20 - Is Databox hiring?
45:00 - Databox on remote working

On this episode we talk to the 10th employee at Dollar Shave club, Cassie Lawrence. She discusses how she joined DSC, when she knew it was going to be successful, advice to other startup employees and much more!

Cassie Lawrence

1:00 - Were you there for the video?
2:45 - The CEO of Dollar Shave clubs advice to Cassie about her career.
4:42 - What was her first day at Dollar Shave Club like?
5:55 - 3 Pieces of advice to somebody joining a fast growing company?
9:22 - When did she know Dollar Shave clubs was going to be huge
12:50 - Did Dollar Shave give equity to early stage companies?
13:15 - Why Cassie decided to go to a small agency instead of a fast growing company
17:02 - How is PR doing during COVID-19
18:30 - Cassies advice to graduating college students

Adam Ryan is the President of The Hustle.

He has been with the company since they were doing $10k a month in business to now doing over 8 figures a year.

Adam joined the company to be the first sales person but now runs the complete day to day operations.

In this episode, he talks about moving up quickly in the company, what it takes and what he recommends to anyone else who wants to move up fast at a startup. He also speak about how things are going at The Hustle during this crazy time, a few tips on how to get an interview and how to get a job at The Hustle.

Show Notes:

2:50 - Spiceworks taught him how to go from 1-100M

3:30 - Why Adam left under armor to joint the hustle

5:20 - Why Adam doesn’t love big companies

6:38 - 10K a month when he joined to $1.5M in a year.

8:17 - What made them change business model

8:57 - What it felt like to go from if to when

10:30 - What Adam uses weeks and nights to keep up with the growth of The Hustle

13:30 - How to be successful at a fast growing company (Adams first question he asked when hiring)

14:40 - Advice to people joining start ups

15:20 - How they’re handling corona. Contingency plans, etc.

17:20 - Is the hustle currently thinking about Layoffs

17:50 - Tools that will not get cut? Sales force and another big name

19:30 - Startups that stand out to Adam

20:40 - Adams billion dollar idea

23:00 - 100 million dollar ideas

24:20 - What Adam looks for in separating yourself as an employee

25:00 - How to get in the door about a company

26:20 - Positions The Hustle is hiring for

On this episode, I talk to Dave Gerhardt (DG) about his time at Drift and now Privy.

He talks about how he was able to leverage a side project to become the 8th employee at Drift.

What he learned about being at company that early.

How he chose to work at such an early stage company.

How he recommends other people think about working at small companies.