
Aaron Schumm
3
APPEARANCES
3
PODCASTS
012
DEC 30
JAN 6
JAN 13
JAN 20
JAN 27
FEB 3
FEB 10
FEB 17
FEB 24
MAR 3
MAR 10
MAR 17
MAR 24
MAR 31
APR 7
APR 14
APR 21
APR 28
MAY 5
MAY 12
MAY 19
MAY 26
JUN 2
JUN 9
JUN 16
JUN 23
JUN 30
JUL 7
JUL 14
JUL 21
JUL 28
AUG 4
AUG 11
AUG 18
AUG 25
SEP 1
SEP 8
SEP 15
SEP 22
SEP 29
OCT 6
OCT 13
OCT 20
OCT 27
NOV 3
NOV 10
NOV 17
NOV 24
DEC 1
DEC 8
DEC 15
DEC 22
DEC 29
JAN 5
JAN 12
JAN 19
JAN 26
FEB 2
FEB 9
FEB 16
FEB 23
MAR 2
MAR 9
MAR 16
MAR 23
MAR 30
APR 6
APR 13
APR 20
APR 27
MAY 4
MAY 11
MAY 18
MAY 25
JUN 1
JUN 8
JUN 15
JUN 22
JUN 29
JUL 6
JUL 13
JUL 20
JUL 27
AUG 3
AUG 10
AUG 17
AUG 24
AUG 31
SEP 7
SEP 14
SEP 21
SEP 28
Sep 7, 2026
VCs chased crypto and passed on his “boring” startup—then he raised $385M at a $2B valuation. | Aaron Schumm, Founder & CEO of Vestwell
38:45
38:55
39:12
P
38:35PabloHOST
Like, what is the playbook that you use to get into, like we said, either Morgan Stanley on that side, or, you know, the long tail of advisors that fed your business for the first few years?

Aaron SchummGUEST
Yeah, I will the enterprise side, right? Because I think that's kind of closer to my core of what I gauge on.

Aaron SchummGUEST
I think you have to look at some of these deals you do is it's a long road that you're marching down and you may not make the right turn or it may not fall into your lap the first time around, but often they come around if you just continue to do it.

Aaron SchummGUEST
When we sold that, the first time we pitched them, I think it was 2018 or 2019, somewhere in there, where maybe 40 people deep and all of us well.
5 MINS LATER
P
44:33PabloHOST
And it's so painful.
Savings Solutions and Scaling Strategies With Vestwell’s Aaron Schumm
3:59
4:10
4:19
4:47

Aaron SchummGUEST
So there are the haves and have-nots, right? And the haves had typically been larger established businesses, right? Fortune 500, Fortune 1000, however you want to kind of bucket that.

Aaron SchummGUEST
Once you start to move to smaller and mid-sized businesses, that's where the participation rate and just the engagement drops off a cliff.

Aaron SchummGUEST
And a lot of it came down to how these things are stood up, like how a plan, like as an individual proprietor, how am I going to put together a 401k plan or a 403b plan for myself and my employees in a way that's easy enough for me to manage and It's cost-efficient enough where it's not going to break my bank as a small, mid-sized business proprietor, right, because you're always looking at your balance sheet and making sure you can support these things.

Aaron SchummGUEST
So you have to look at it from all the different viewpoints of who engages because there's a lot of people that it takes to support a plan.
How Vestwell Is Closing America's $50 Trillion Retirement Savings Gap with Aaron Schumm
10:07
10:21
10:35

Aaron SchummGUEST
where AI is kind of in everything we do, right? It's like there's not a day you're not touching AI in some capacity, right? And it varies by role, obviously, across the organization.

Aaron SchummGUEST
So about probably about three years ago, we started on kind of the AI journey, right? And we thought about it and said we looked at our data set and said, OK, the world's going to go there, right? We don't know how fast.

Aaron SchummGUEST
So how do we make sure that we're set up for that future and what's going to happen? So if we started with the data architecture layer and restructured it all, and a lot of that was thinking about, okay, how are we going to do this? You know, whether it be, you know, you think about, I think about broadly in two vectors, right? The internal what I'll call like operations support service experience that can be augmented through AI.
8 MINS LATER

