1. Why are you so involved on Instagram? / What do you gain from it?
I love your generation and it allows me to get a glimpse and experience it. It also allows me to share whatever positive things that I’ve learned and hopefully prevent others from making mistakes I made. It can also be very funny. -RH
2. What do you dislike about Instagram?
People who are negative, condescending, self-righteous, pretend they know what they don’t, rude, judgmental, or worse yet….mean. -RH
3. What would you say is your worst quality?
My worst quality is I’m loyal to a fault. But my best quality is I’m loyal to a fault. I’m never going to change. -RH
4. What would I say is your worst quality?
I try to facetime you too much. Key word try, usually doesn’t take. -RH
5. What is the average time it takes for you to respond to an email?
As long as I’m not currently with someone, talking to someone on the phone, or asleep, within minutes of you putting the punctuation mark on the last sentence of what you just emailed me. -RH
6. What is one of your top rejection moments that made you who you are today?
When your mom ghosted me after I met her at a bar in Mexico and then I had to track her down after the vacation and convince her we were gonna get married…she was confused. -RH
7. Crocs or Uggs?
Crocs for casual, Uggs for dress. Duh. -RH
8. Why don’t you play golf?
My free time was scarce and I always preferred to be with the fam so I never learned. To this day, the only ones who can get me to play golf are my sons and it’s literally just to hang with them. -RH
9. What do you hate?
Bullies. -RH
10. What were you like in high school?
Shy. Awkward. Funny. Small. Insecure. Perceptive. And again, funny…not to brag or anything but I’ve been called the songbird of my generation. -RH
11. What do your high school friends say about you now?
I have no idea why he’s done well. He never seemed that smart in high school. -RH
12. What do you see sometimes that bothers you?
When people want their friends to be successful, but not too successful… -RH
13. What was your favorite deal you have been a part of to date?
The deal when I came to Jefferies from Drexel. I was 29, I was offered multi-year seven figure salaries to go to large firms on wall street and I decided to take a $50k salary and the right to take a small percentage of our groups bottom line in shares of the company. 30 years later I still can’t believe how brilliant and nuts I was at the same time. -RH
14. Best piece of advice today?
I will give you two. First, open your eyes, mind and heart so you can be an active and aware participant during this painful and complicated period of Covid. This experience will then not be a negative waste and you will gain a lifetime of benefit by learning and getting true perspective on life. Second, wear a mask. -RH
15. Your competitors are almost all incredibly giant banks. What do you think about that?
I absolutely love the fact that for the past 30 years our team is relentless and just keeps coming and coming every single day. Sometimes it’s a huge advantage being an underdog. Never give up. Never. -RH
16. You’re Best Gift?
Being a good judge of character and surrounding myself with quality people. -RH
17. What was the last thing you stole?
I like unusual small whacky drinking glasses. I don’t know why. I see one I like every 5 years at a restaurant and have to steal it. I always leave an extra hundred dollars out of guilt. But I get the glass. I know, weird. -RH
18. I’ve heard you yell on your Peloton…who’s your go- to instructor?
Olivia Amato (@oamato). A friend told me she used to work at Jefferies. She must not have liked it because she seems to be taking it out on me. -RH
19. Your favorite movies?
Not in order: Tommy Boy, Braveheart, Step Brothers, Pulp Fiction, Godfather(s), anything Austin Powers, Matrix, Talladega Nights, Love Actually, James Bond, Wedding Crashers, Princess Bride, Pitch Perfect (even 3), yup I said it, Bridesmaids. -RH
20. What is the best way to win a negotiation?
Listen closely and prioritize the long term. -RH
21. I’ve heard you yelling and laughing with Carl Icahn on the phone and then your next call you are doing the same with Bill Ackman. I saw them on TV and they don’t seem to like each other. How do you get along with both?
Always get to truly know people versus judging them by what other people claim to know or what they may have heard. -RH
22. Who worked for you that left that you wished never did?
I hired Dan Loeb in 1992. He left a few years later. I told him I was mad at him for leaving and it probably wouldn’t work out. He’s nice enough to not remind me every time we have lunch and I appreciate that he never just decided to personally buy our entire company. -RH
23. Mike Milken seems to call you almost every day. What do you talk about?
It’s usually Mike adding to my list of everything I could be doing better and me writing it down. -RH
24. What is the secret of success in your industry?
Getting people to trust you and never letting them down. -RH
25. Are you really good at math?
A long time ago I did a personal option trade and was certain I made $1,400,000 on a $14,000 investment. It took me 2 hours to realize my profits were $1,400. Those friggin decimal points. -RH
26.(Bonus) Lastly, when will you retire?
When I can no longer contribute but hopefully never. I don’t do well with free time, ask your mom. -RH