Jeremy Milken — Watertower Ventures

Posted on Tuesday, June 1, 2021

Jeremy Milken is a partner at Watertower, a serial entrepreneur, and just a lot of fun to talk to.  

We talk about his own journey, his views on deploying money into the venture asset class, his partner Derek and his wife, the flexible neurotic.

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Jeremy Milken is a partner at WaterTower Ventures. Prior to WaterTower, he was a founder multiple times with several successful exits. He started his career in investment banking and private equity, has been an entrepreneur for 20 years, and is now on the other side of the table.

We’re in his beautiful office here. Hi, Jeremy. 

Great to be here. 

Is it really?  You were the hardest guest to get on! 

Well, I’m Sorry about that, but, hopefully it’ll pay off even though it’s unlikely. I would say, so. 

I think you said it’s going to be a better episode than Derek’s. 

Yes, I can guarantee I’ll be better than my partner Derek that’s for sure. 

Okay, great. let’s start there then. Great place to start WaterTower. So, you’re the newest partner? 

Yes, that’s correct. 

And this is Fund II.

Fund II, yeah, exactly. So uh, yeah, I can give a little overview on WaterTower. So, uh, we are a $50 million, what we call a first institutional capital fund. We’d like to invest just right after, I would say the friends and family round kind of at the earliest stage, check sizes, you know, probably the half a million to $1.5 million range.

In terms of our focus, we, you know, I always say I hate buzzwords, but we, uh, we’re focused on the connected consumer on the evolving enterprise, my personal background is in the enterprise software category.

My partner, Derek, leans more towards the consumer media side of things. Um, and, um, you know, I think it’s just. Talk a little about kind of what we, you know, what our differentiators are, I think would be helpful as well. One is, you know, we help our companies with access to following the 

you know, Derek well, Derek was, yeah, Derek

Derek knows everything. He’s the ultimate social butterfly. That’s what I said about Derek.

That’s funny. He is. He’s always like you want to hang out? Sure. Hang out. 

Exactly. Exactly. So. Derek’s been a venture banker for over 20 years and, has a lot of experience in the financing categories. So we provide, you know, our portfolio companies, really great access to follow on capital.

It’s one. of the things We do. And we always say that if you take money from us, you’re never going to knock on a cold 

door. 

uh, for follow on financing. I think also we have, 

Can I ask you a question about that? Is that usually a series a and, and I asked because I see you folks pushing really early, mostly in these sub $10 million valuation.

Yes exactly. I would say ideally we’re. I mean, so valuation, you know, like it’s there there’s a hard valuation cap where we enter deals. But, yes, I think normally we’re in single digit opportunities. 

Because often when we entered, there’s still another round after us, before the series, a lot of times.

Yeah, I think it depends. It depends on the situation, I think. Um, and obviously every situation is unique, but you know, like I said, that, that that’s the goal. from our perspective. 

Never knock on a cold door. 

I like that. Uh, that was number one. 

Yeah. Also I think, we have a lot of, uh, you know, Derek and I have been in the, in, in the the business for 20 years.

Um, Me more on the, on the founder side Derek on the banking side. So we have a very strong corporate relationship network as well. And we use that to help our portfolio companies kind of cut through you know, I would say the time-wasting, right. um, and, uh, and you know, and see if there’s opportunities selling their product you know, whatever large customers, et cetera, we can help cut through that. Um, and then I think, you know, the the last point is really just operating expertise, right. And kind of, I would say perspective on things. So. We, um, you know, we’ve, we’ve, we’ve lived through multiple downturn cycles you know, up cycles and down cycles. we both been multiple time founders as well, and we have, had You know, success and we’ve also suffered, So, uh, you know, I think we can bring a lot of great perspective, uh, to the portfolio companies, um, and, and, and help them, you know, it’s, it’s, it’s, it’s, it’s a difficult process, right.

I mean, I’ve been through this several times in my career and it’s, it’s not easy. 

Yeah, but you kept doing it, right? Like you’ve been a founder, multiple, multiple 

times. 

Well, the joke is The joke is, is that I started out my career, obviously working in a traditional job and I quickly realized that I was 

unemployed. Right, right. You had a boss briefly. 

exactly. I just, it just wasn’t for me, it wasn’t for me. And, you know, I think, I think it’s just kind of the mentality. Right. It’s like, you know, if I like to, I like to kind of exist in more of a. Ambiguous kind of risky environment. 

That kind of, uh, environment. I’m a, you know, you’ve, you’ve been 

at it, but that’s why I’m a VC now because the highs and lows 

it’s difficult, but you can look, I mean, like I said, there’s there’s, there’s no lower, low, and there’s no greater high.

Right. Um, and I think that’s, uh, that’s kinda my perspective. on it, so, 

Well, yeah, no, I don’t. Um, you were, I think I told you the hardest guests to research and the hardest guests to get on, but there’s not much about your past or you don’t do a lot on social media. It’s suffice to say, tell me about some of your founder journey, maybe your most recent 

company. 

Yeah, sure. Absolutely. Yeah, so Obviously, I, I, I’m definitely not on social media. I don’t know if that’s a good or a bad thing. I think I was just saying I don’t have 

time. Oh, right, right. Good. That’s strong Kim bother. 

Yeah, no, no, no, no. There’s no good reason. I just, just, it’s not part of the workflow. Um, but yeah, we can talk about my most recent, company, a company called workspace.

it was a commercial real estate enterprise software company. The websites go workspace.com If anyone’s going to take a look at it. Um, I partnered with a guy prior to that. I’d been in the, uh, in the ad tech space for several years and a partner with a guy, um, who I had done business with. We actually in the, the senior care category, one of several categories we were in together. but, Um, and his wife was, uh, actually worked for a company called Lincoln property company, which is a big property management company in the United States. Um, and he went into their office one day and he, uh, he sat in the office, this was like an. 13, maybe early 14. And he sees, a work orders coming over on fax machines and he sees binders of COI sitting on the tables, et cetera.

And he sees them FedExing manual checks around the United States for payment. And he said to himself, this is, You know, and meanwhile, the company’s managing probably close to a hundred million square feet of commercial office. And he’s like, this is, there’s a huge opportunity here. So, so started the company with, um, building a, uh, you know, very simplistic, just simple work order system right. where you could enter work orders.

Uh, the tenants could log in and put work orders into, uh, just kind of a workflow system. and, took that from it to an, uh, a full property facility management system that you would use to operate kind of like this building you were in today, everything from visitors security to vendor management. to kind of payables, workflow, 

et cetera.

And how did it start? So you started and did you hire engineers initially? Like, what was 

Well, my party apps on my phone, my partner, is, is an 

engineer 

by 

trade. 

Right. That, that, that, that that’s 

his, So 

he literally, he just coded it 

himself 

basically. Yeah. And we started kind of working, you know, kind of with, in conjunction with basically Lincoln property company.

They 

were 

you know, they basically gave us kind of all 

the input 

that we needed to 

build 

this 

system. 

Um, and, uh, So that, that’s 

how 

it 

started. 

uh, yeah, give me more of that sort of founder journey. So you were, what were you, were you the 

CEO? of the company. Yeah, exactly. And, you know, we started, it was like, a, you know, super small company.

It was just really just like 

three 

people. 

kind of thing. We ended up, you know, very shortly thereafter after building the system, rolling it out basically to the entire 

liquor property 

company. 

Right. So we had very explosive growth with it. then we ended up kind of really falling into, I guess you could say, kind of a, I don’t want to say it was luck necessarily or not, but, getting feedback from them, they came to us and said, Hey, you know, we, we have a problem where we have to allocate, you know, they, they manage buildings on behalf of maybe 20 or 30 different.

owners in the United States, maybe more at certain times, and every owner is on a different accounting system, a different chart of accounts. And like, we have this challenge where we get a bill, like a centralized build. We need to allocate it. We’re logging into 20 systems to input this information. So we said we can solve that problem for you.

Right? So we went in and we basically, you know, wrote integrations with all the major real estate accounting systems to from simplistic perspectives to post payables information. Uh, so they could set up pre allocations and post the bills After we did that, we said, wait a minute. Well, We can’t, we know that it can be posts to this data, we actually can pull 

the 

data 

as well.

And, uh, and that really kind of made the company. Um, we built kind of a industry leading asset management product, out of that. he’s the example of Angela Gordon, which was one of our big customers. they, uh, had 40 joint venture partners. Everybody’s on a different chart of accounts accounting system.

So we provided the layer of the platform for them to aggregate their portfolio data. Before that they were getting PDF books every month. of people sending in and they had people in New York typing and information to spreadsheets, to aggregate the portfolio. And We basically provide real time data connections to that.

So, and you know, and then I think the, the reason why we actually have a grow quickly was really because we were fortunate enough to take advantage of a of network effect. Right? So the example was, you know, like we would enter, you know, we would have the owners, like an Angela Gordon mandate that if they wanted to do business with them, they had to use our product for reporting purposes.

Because it was so efficient for them. Um, and then the owners we would integrate with the, with the JV partner and the JV partner might have one building with Angela, but they might have another 15 or 20 part properties with other people. And once they were integrated, we could 

light 

up 

the 

system 

for 

them.

Then they would go to their other partners and say, Hey. This is such a great system. And then they would it went and we just created like 

a chain. 

Yeah. 

with the product. 

And did you have Lincoln from the get-go kind of paying you so you didn’t need to raise money 

yeah, we actually ended up never raising capital for the business. which is always sucks. I always joke that it’s quite 

quite 

amusing 

now 

that 

I’m in 

venture capital business, because I used to spend my days, not taking money from venture capital, companies. right.

Everybody’s calling me to invest. And, um, now I spend my days convincing people 

to 

take money 

from people 

like me. 

Great. 

Um, no, So we bootstrap it. Yeah, exactly. I mean, we were, we were Very fortunate and very lucky with that. Um, we never, 

need 

to 

raise outside 

capital. 

How long did you do it? Journey to the end.

Yeah. So we, uh, we built the company up over a period about 

five 

years. 

Um, yeah. And we had, and we sold the company to a private equity company up in San Francisco because we had it bootstrapped obvious. It was a great outcome for us. We sold the company in September of 19 and, you know, we had about half a billion dollars, half a billion 

feet 

on the 

platform 

we sold 

it.

Um, yeah. So it was, it was, it was pretty significant, uh, um, uh, product and yeah, and it’s still going strong. Um, and, uh, You know, they, bought a hundred percent of the company and, uh, that that, that, 

that 

that. that. And it was up into the right the whole time. 

Yes, it was up until 

the 

right the 

whole time. 

Pretty much. Yeah. I mean, I think, you know, I, I would say that we, um, we, uh, it was up until the right, but we realized, you know, like I said, through the process that just being a property facility system, I don’t think was going to get us to the next level of where we wanted to be.

Right. So. I think we got you, know, got to a point, we kind 

of fell into 

this other 

product, 

um, which 

ended 

up transforming 

the company. 

So I would say 

obviously, 

like everything, 

it was 

luck, 

A lot of it 

was 

luck. Right. Um, but, uh, but in that specific 

opportunity 

we 

did summer and so, right. Okay. Good. Good for you because you’ve done a number of other companies before this.

did you set out, do you know, do you think of yourself as setting out to build sort of startups or what did you set out to think I’m building a different sort of company bootstrapped sell the private equity. 

Yeah, no, I, I don’t really think about outcome, I guess so much Right. when I when I get involved. I mean, maybe, I guess you could say that that’s maybe a good thing or a bad thing, right?

I mean, I think more about the value proposition, you know, what, what the problem solution type thing is in, in, it. Um, I, um, that I would say that our goal was not to sell 

it 

to private 

equity. Right. That was not our goal, obviously. but I think, you know, it, it goes to that kind 

of 

situation where. You know, you evaluate every offer and every opportunity.

Right. And I think, you know, I, and I think our perspective is, is we had the opportunity I mean, to let’s say, sell the company for the same valuation that we would have 

financed 

it 

for. 

Right. 

and, uh, so it was a very significant trans, you know, let’s say significant, you know, sale opportunities. So we decided, Hey, you know, let’s, let’s take advantage of it because we don’t have any investors.

Right. So it’s not, you know, it was just the two of us, 

And in 

retrospect, 

we 

look 

smart, 

right. Because, because obviously, you know, as we’re sitting here in person, right. Um, together today, 

um, 

you know, I I think the building, I think this building today is, you know, for the last, uh, you know, whatever it’s been since it started the pandemic, it’s been a it’s not, it’s not even 10% occupancy 

here today. Wait, wait a second. When did COVID happened? When did you sell it? I didn’t, I wasn’t putting those together. We 

September of 19 

and co and COVID was 

March, February, 

March 

one. So that seems kind of brilliant. 

Yeah. Well, there was, no, there was no plan 

to 

be 

brilliant. 

That’s for sure. Like I said, it goes, 

It 

was 

just 

pure 

luck, And then, and then soon after doing that, which sounds like a good success, you’re like, great. I’m going to join water tower. 

I mean, it’s been longer than that, right? I mean, 

first 

of all, 

I’ve 

known 

Derek for 

20 years. 

Okay. Derek, Derek was actually an investor in my first, company.

I started in, uh, Two I think it was 99, 2000 when I was much, much younger, but, in the, and that one had a lot of 

pain 

and 

suffering, 

so we’ll 

skip 

over 

that time. But he was a, he was a banker then, or he was it. 

Now he’s part of a fund then he was part of fun 

then. Yeah. Yeah. Yeah. So, um, so, um, and, um, 

yeah, 

so, okay, so skip 20 years there. 

we’ll see. We’ll just fast forward. All the pain and suffering 

and everything 

was 

on how great.

I am here today. Right. Okay. 

your brilliance. 

Yeah. So, like I said, I’m no Derek 20 years, I was an investor in in the prior fund. I actually chaired the ELPAC committee of the prior fund as well. 

you do anything that’s cheering the out back? 

 in terms of activities to turn the ELPAC, no, because there was a to do in that, but in terms of working with Derek, I was actually working pretty closely with Derek over that timeframe, just because I’m super 

passionate about 

this category.

and you know, over the years I’ve invested, I would say informally. You know, and I’ve I’ve done that throughout my career. And, um, so I’m just always interested in this category and looking at new opportunities, new businesses. I love working with founders. Like it’s just one of my passions, like I said, for better or worse it’s something I enjoy doing.

Um, so, Yeah, I was working pretty closely with Derek over the, uh, let’s say three year investment horizon of 

the prior fund. 

Um, and, um, you know, we, we had loose conversations about it, right. Obviously I had my company and, uh, And I wasn’t going to leave that opportunity to join water tower. you know, I think for lack of, a, some great story that I could give you, I think it just, the timing just kind of 

worked 

out 

right. perfectly.

Right. It’s kind of like he was, you know, he had, he was finishing as the investment cycle in fund one. He was ready to get started for the, for fund two. And, um, I, uh, I just, uh, you know, I just sold my company and then we just came together and was perfect. And the great part about it was we started fundraising actually.

Uh, in, uh, in February of 2020 about, I think it was 

one 

week 

before 

the 

LA 

lockdown. 

So it was, uh, it was, it was definitely very interesting 

times. 

Let’s put it that way. 

Didn’t have to travel though.

True. Exactly. Exactly. Exactly. So,  you know, we closed the closed fund, July 31st of uh, 2020. And, um, you know, it’s been great. I mean, like I’ve been, 

uh, 

you 

know, 

I’m definitely 

enjoying things, $50 million. Yeah. 

And, um, so it’s, a, 

it’s 

a, 

uh, 

it’s 

been 

great. 

Uh, it’s been great. W well, let me think of my question there. Uh, how do you, when you looked at Watertower, like, how did you think of the VC ecosystem?

Like, did you think about, Oh, I’ll go join Mark Mullin over at bonfire. Like, you know, you know, I’m not trying to pick on Mark. 

well, I don’t, I, I don’t think Mark 

Mullen would ever hire 

somebody, 

like, 

me, you know?

So, no, but I mean, 

how did you think about water towers place in the ecosystem? 

Yeah. Well, I think, look, I mean, obviously I’d have been an investor with Derek and I’ve known him for 20 years.

Right. So I, you know, I think my view on the situation, I was looking to get involved with somebody, 

um, 

at the ground 

level. 

is 

my 

view 

on the 

situation. Right. 

Um, you know, we, uh, and, uh, so, you know, I was looking for an opportunity 

to 

enter 

ground level 

and I was also looking for the 

right partner. 

Right. And I think It’s an important thing. you know, so I was looking for a partner. I think that could, that, that would be a good compliment to me. Uh, you know, we were joking earlier about Derek, you know, in the sense of that, I would say that I would characterize Derek 

as the 

eternal 

optimist.

Um, and Like we already talked about it, the social butterfly, and, uh, you know, I, I would say that I’m, I’m not a polar opposite to him necessarily, but, you know, I, I always say I’m a cautious, cautiously 

optimistic. 

And, uh, and uh, definitely, I, I, you know, I, I don’t compare 

to 

him 

for the 

social 

butterfly 

perspective.

He said that you secretly love all the 

VC parties though. That’s what he 

said. 

Yeah. Well, you run an event, 

you know, you’ve heard of it, you know, exactly. Last 

you. 

Yeah, exactly. Obviously I was enjoying myself. Um, but, um, you know, so I was looking for a partner. I think that could, that, that would be a good compliment to me. Right. And I think that, um, and, uh, that’s what Derek provides really. Right. And, and I think obviously Derek has a, uh, You know, very extensive relationship set in the venture community.

I, you know, I have that obviously now that I 

didn’t 

have it originally. right. 

So, so I think it was just a good partnership all along. I mean, I think that, I, you know, and I think also from terms of our own personal focus, I’m probably more focused, operationally, with the portfolio companies, I would say.

and you know, I definitely definitely lean harder on Derek, um, in terms of the, uh, you know, financing and, You know, relationship, 

network 

building 

and 

stuff 

like 

that. So, 

and do you have a, would you say your network, you’re looking at more the enterprise space and you have more of sort of like corporate relationships?

Yeah, I would say, I would say that I’m looking. Yeah, I’m definitely more, I want to say solely focused, but pretty focused 

on enterprise 

software 

Right. That, that that’s, that’s where I I’ve had my success and I have a lot of kind of knowledge in the category. And I would say in terms of the corporate network, you know, w I would say corporate network, rarely from the finance financial side of things.

Right. More so than, let’s say the media companies. I mean, obviously I know a tremendous amount of people there, but I would say more so on the financial markets type stuff, obviously the real estate industry, you know, the hedge fund industry, just things like that. I have a lot of, private equity, a lot of deep relationships there, um, which are advantageous for certain types 

of 

enterprise, 

you 

know, 

companies that 

we’re 

pursuing. Yeah, definitely. I think Derek. Duh. I think Derek doesn’t, I’m not sure how to say this, but I think Derek doesn’t want, I think Derek’s roots are kind of in digital media and I think Watertower really has evolved, especially with you here to have a broader focus of he’s still got digital media, but having you means it’s a lot more enterprise SAS type folks.

Yeah, I think so. I mean, I think that we, um, you know, the prior fund there were some various we have some successful investments in the enterprise category. Um, and, um, so. yeah. Look, I mean, I, you know, I I always like to, you know, everybody wants to say that they’re not, th they don’t operate reactively necessarily 

right In business that They’re proactive 

for say, or their, or their thesis driven to 

hit a 

buzzword. Um, you know, but I think, you know, look, I mean, we, we, you know, I wouldn’t say that we have, you know, we, don’t have like a mandate or a absolute, you know, like we’re only investing in this and we’re not going to look at that type of thing.

Um, we, uh, you know, we’re, we’re broadly focused, right. Just so happens that, you know, a lot of the opportunities, uh, out of the first five investments we’ve made in the current fund, a lot of them are more, I would say lean more towards the enterprise side, 

yeah. Do you want to talk about a couple investments you’ve led or companies you’re leaning in on? 

Yeah, sure. Absolutely. Yeah. I always say I have to take it the, uh, The opportunity to, uh, to promote as as 

Derek, 

would say, 

yeah, 

I, one of our portfolio companies, but yeah, look, I mean, we’ve led four of our first five transactions.

we co-lead the fifth actually. So we’re heavily involved with the portfolio. Um, right now the one company we’re talking about probably as a company called Seesaw. the website is, uh, ccu.co. it’s a, uh, residential real estate. transaction management 

platform. 

and, uh, we, it’s kind of like an all-in-one platform for 

residential real estate from managing lead process to, you know, putting listings into transactions all the way through closing.

Um, you know, the vendors are involved, brokers, involved, title, escrow, et cetera, across the map. Right. And it’s actually quite an interesting company companies based in, I’m based in Utah. We’ve been spending quite a bit of time out in Utah. Um, it’s we have two investments out in Utah in the fund, um, and, uh, it’s been a, a, you know, the company’s doing extremely well.

They have about 40,000 users on the platform they’re processing, I’d say around 15,000 transactions a month. We’re We’re, we’re big believers, in this, uh, you know, I don’t want to, say, I don’t want to give us credit that we’re contrarian thinkers, I wish I wish it were that smart, but the, um, you know, everybody in the venture business, I would say Well, not everybody, but a lot of the venture capital. in the real estate market is going towards 

displacing 

the 

brokers. 

Right. Um, and you know, it was interesting. when you look at these I buyer platforms, you could say, I mean, less than 1% of transaction volume in the real estate industry goes to those platforms, Meanwhile, these, some of these 

companies 

have 

raised 

hundreds of millions 

of dollars.

Right Now. We can talk about what the future is and all that kind of stuff. But the reality is, is, you know, 99% of the transactions are going 

through brokers. 

And we don’t, think there’s a lot of innovation 

in that category 

today. And CSO provides really one of the industry leading platforms in, in 

that category.

Um, and there’s a lot of characteristics about it I mean, it’s an, it’s an independent platform it’s independent of. Let’s say the Zillow’s or the, or the, or the  real Ajai or, or, um, you know, KW command with Keller Williams or all these different internal systems or Compass’s 

system. And then, 

you know, I think the brokers like it because they feel like they, they control their own destiny.

They own their data. Right. It’s it’s not, it’s not being 

housed 

at 

Zillow 

as 

an 

example. 

Right. 

Um, 

and it’s been a very valuable 

product, so 

yeah. So we’re probably the gearing up I’d say in the next, uh, you know, probably a month or so to go out and raise 

a series, 

financing 

for 

next. Very cool. So I want to probe on this, not being contrarian, but having a bit of contrarian in you, like where Jeremy are, you kind of contrarian 

when 

you 

look at 

sort of venture.

Yeah. I don’t 

Let’s say that that’s 

too 

difficult 

a question. 

think many for this. I mean, you know what I mean? I thought 

they were going 

to 

keep it high level here. It’s too. It’s too difficult. Um, you know, I don’t, I don’t know initially how to respond to that, I mean, I think, I think, you know, obviously we look at it on a, on a, um, on it, let’s say we can look at it from a track transaction specific basis.

Right? I mean, I think our perspective is that. You know, like everybody in the business, we’re looking towards the future, we’re looking towards future trends, right. So we’re trying to evaluate maybe what people are doing today and saying to ourselves, you know, what are people doing today? Is that a good thing or a bad thing?

You know, in terms of the venture market in general, being a contrarian thinker, I mean, you know, having been a founder multiple times I would say that we’re sensitive to have to, I would say founder dilution, raising money at the right time, you know, for the company, you know, I think sometimes people you know, can fall into a trap of, of, uh, of raising too much money. Right. And, you know, look, you know, this it’s a long 

journey. 

mean, 

as you 

know, 

from your 

experience, right, I mean, it’s a long journey and you know, Uh, you know, all you do is read about, you know, every, every minute you read about this person raised that and this person raised that.

And it’s, you know, it can get kind 

of, 

I don’t want to say caught up and that a little bit. Right. Um, but you know, it’s funny, like, you know, the most successful 

businesses 

are 

not raising. 

okay. 

Right. And, and I, think that the people, sometimes they don’t really, you know, they need to really think about that. Right. You know, so. So I think it’s a, that’s kind of, I don’t want to say that’s our contrarian perspective because obviously we’re looking to put capital to work.

Right. But but I think, you know, that’s kind of our view right. in the sense of, you know, we, we kind of come from the mindset 

of, 

we want to raise the capital that we need and when 

we 

need 

it. 

Right. and, and we want to protect ownership, you know, for our 

founders 

and 

really 

for 

ourselves 

as well. Let me ask you a question on that.

Like, is there anything concrete you can say, like if, if a company is coming to you and the founders of less than. Half the company that they own or something like, do you have any rules of thumb there that you’re looking at? 

Yeah. I mean, I think, I think in a general perspective, I mean, if 

you 

asked me what what’s 

vanilla 

right.

Series a transaction, 

right. okay, we want the owners going into that transaction 

owning 

half 

the 

company. Right. I mean, that’s kind of 

our 

goal, 

In advance of a series, a financing, ideally, maybe even a two thirds 

ownership 

of the 

company. Right. 

And we didn’t go into it much, but you started your career in private equity or investment banking.

How do you see that relationship with VC private equity and a lot of the,  the public market people coming into private markets? 

Yeah, I think it’s very interesting these days, right? I mean, it’s, a, you know, the, um, you know, obviously we, we sold their private equity company that is interested in buying as num numerous ones in the Mark that they bootstrapped Non venture backed, you know, SAS businesses. Right. And there’s a number of companies that do that today in the marketplace. And, um, you know, it goes back to kind of 

a, 

you know, so how does it 

compare? 

But they wouldn’t wait on that point, but they wouldn’t buy the company. They wouldn’t buy someone who was venture backed.

It’s something they wouldn’t buy somebody that’s venture backed. You know, the problem is, is that, oftentimes the. Valuations right. Are, 

you 

know, we 

can talk 

about the 

general 

venture, market. And then we’ll, we’ll, we’ll we’ll flip it into that discussion. But yeah, so obviously the venture market today, um, as you know, right. I mean, it’s, it’s become incredibly competitive with the late stage financings, um, and that’s kind of trickled down even into, you know, even the series a level financings, I would say today. Right. I would say what’s, what’s quite interesting is where we kind of operate you as well. you know, valuations, You know, have remained pretty much constant right? over the last five years, I would say, or within the range of constant wall, series a financing, might have made it valuations have tripled, And then you know, you get later maybe even quadruple. so I would say that, you know, so anyways, so that’s kind of that, that, do with the top heavy nature of the venture capital market today. Um, so the private equity companies, but Obviously there’s that, there’s the traditional, private equity companies that are not looking to buy these types of businesses, 

but.

A lot of, a lot of these, I would say mid tier type private equity companies um, are looking to get into this business because like everybody else they’re searching for growth and opportunity. Right. And you know, the premium that’s been paced on growth versus value in the last, you know, five years has gone is just crazy.

Right? I mean, growth 

is 

so 

much 

higher 

value 

than 

value, 

let’s say, right. That, which is good for us you know, in the room, but. But it makes it difficult, right. For these private equity companies to put capital to work everybody needs to put capital 

to 

work. 

Right. 

Um, and um, so in the sense of that, you know, our people, are people, 

um, 

uh, 

you know, why would a project we can not get involved with a venture backed business?

Um, well it just depends on kind of what stage it is. Once a business goes really series a financing. My perspective is, is that, you know, first of all, the valuations are 

high. 

Okay. So, and in addition, The businesses are usually going 

into 

some 

type of a 

growth 

mode. 

Right? 

And you know, it doesn’t really, and and the private equity companies are not They’re not set up for high 

growth 

investing. 

Right. They’re set up for 

more 

of 

kind 

of 

like, 

I would say moderate 

growth 

investing because what 

I would say. Right. So, so, you know, they’re looking for those types of companies that can kind of fit into that mold. I would say, like I use see Susan 

example. I mean, 

it’s, virtually almost a profitable company today. so they have had a tremendous interest from the bootstrap private equity 

guys. 

 And, um, because it fits into 

that 

mold. 

Right. 

Um, and, uh, so, so that’s how I kind of look at it. So I wouldn’t say that that the, the private equity, the mid tier guys are not wouldn’t purchase a business that was 

venture 

backed. I just don’t think it’s really the type of company they’re looking for. And also the venture investors, right. At the series a 

levels. 

And 

in past that. They’re 

not 

looking 

for 

that 

type 

of an 

outcome. 

Yeah. So like, if, if CC was getting approached by private equity, let’s say they continue to do well, continue to get approach.

They continue not to raise their series a because they don’t have to. 

How do you 

counsel them? 

I think it’s an excellent question. Right? I mean, I, I, joke one of the positives is, is 

that 

we, 

you know, w 

w we’re 

not 

the 

final 

decision 

maker, 

right? Yeah. 

Okay. 

Sorry. 

It’s mixed. 

So I think so I think it’s an interesting thing.

you know, always choke is, you know, It’s it’s always easy when you don’t have to make a decision yourself. Right. So, I mean, the founder is going to 

make 

a decision 

on 

what 

works 

for him 

Right. I mean, he owns a significant portion 

of 

the company. 

Um, and, um, you know, we would just kind of counsel that, you know, it’s, it’s just, it’s just an opportunity.

It’s an opportunity. Trade-off right. It’s it’s it’s what is a, you know, what does an offer today? Obviously, you know, a lot of factors come into what’s what’s the founder’s personal situation, you know, things like that, obviously. Um, and what the potential is of the business. Right. As well. And, and how, and how, how, how close are we 

to 

that potential 

Right to, to being able to get to the next 

level, things like that.

Um, and uh, so, you know, you’re weighing all those, all those factors. I mean, I, like I said, I don’t, you know, it’s, it’s, it’s, it’s a discussion that, you know, we will have, Right. um, you know, and, uh, our perspective is, look, I mean, like I said, we’re, w w we’re, in the business of supporting our founders. And a great outcome is a great outcome, I mean, you know, it’s, it’s, it’s uh, it’s you know, like I would say, it’s, as you know, from your experience, it, it, it’s very 

hard 

to 

get, 

to 

have a 

successful outcome.

Right. And to get an, and I always say to get liquidity,  So, you know, I mean, even myself, I’ve been involved in companies where I’ve had on the verge of selling them. And then two years later they’re bankrupt 

One more question with the private equity and the CCU example, what the private equity person come in and actually allows you to continue operating, like, how does 

relationship work? 

Well, 

I mean, I don’t know of a 

specific, 

specific situation, No, but I mean, like, I can tell 

you 

from 

our 

perspective, 

right? I mean, we, you know, When these companies are coming, in, what these companies are doing is they’re kind of building, I would say kind of like I use the example of like Vista equity partners, 

obviously 

significantly further, 

down the road, but they build kind of like a shared, they have like a shared 

services 

kind of 

theme 

or 

goal 

where they have a shared services group.

And then they want to latch on right. all these vertically vertical kind of SAS businesses along. it. So they’ll have like shared technology, shared marketing, shared HR, et cetera. And they can leverage that across all 

these 

different portfolio 

companies. So. 

yeah know, I think, I think in the examples, you know, a lot of these companies they’re looking to purchase, I mean, it’s all over the 

map.

Right. 

But 

some of them are looking to buy 

a hundred 

percent 

of the company. 

But 

I would say that, you know when. The private equity guys get involved. They’re looking can you make significant investments right there. They’re not looking 

to make, you 

know, to buy 15% 

of the 

company, 

or 20% 

of the company right there. They’re 

looking 

to 

buy 

control 

positions 

in 

the assets 

and 

whether the founder stays or not.

I mean, that’s kind 

of, 

you 

know, 

just depends 

on the 

circumstances 

would 

say, 

right? 

Each one, 

Every 

situation 

is 

unique. 

Um, 

And so I think you said you’re involved with your family office investing. And will you invest in private equity?

Do 

you know, do 

do a lot of private market investing as well as public market? yeah, yeah, I think 

we can talk about the family office obviously and we have a significant family office operation. I wouldn’t say that I’m involved in the family office investing activities. I 

do 

my 

own 

thing.

It’s kind of what I do Yeah. I mean, you know, we say that we have a very talented group of people over there, that work on all of our activities I mean, we invest. everywhere in anywhere across, across the spectrum pretty much. And we also do a tremendous amount of, uh, philanthropic work as well.

you know, we have the milk and family foundation, the websites, uh, www.mff.org. If people want to look at our programs, we’re focused on education and medical research. Also, we also have the Milken Institute I’m sure everybody is familiar 

with the global conference 

that 

host. 

Um, so. You know, there’s a lot of activities going on in the family office.

You know, also I think that we have, you know, some 

very 

smart 

people over there, so 

that 

are smarter than me, 

So, you know, it’s not, I, I don’t think it’s a good use of my time, but I think it’s, you know, I think it is worth talking about not so much what we’re doing over there, but just giving some perspective. I think your listeners might find it.

Interesting.  you know, I would say a decade ago, speaking for our family office, we had zero 

exposure 

to 

venture 

capital 

right in the market. And I think it was it’s. it’s interesting. And, uh, you know, I think maybe about seven years ago, I think we made a decision to you know, focus more on the, on the venture category, primarily from the, from the mid to late 

stage 

investment category.

and, you know, as everybody that has invested started investing that it’s paid off in a significant 

way. 

Right. and you know, and I think that we’re, you know, obviously we’re continuing that and we talked about the growth premium that’s priced on assets today. Um, so, you know, we’re, we’re expanding our venture 

focus, 

I would say.

but at the same time you know, I would say that we have virtually zero 

exposure 

to the early 

stage 

venture. 

market. 

Why is that? 

you know, I think it’s a good question. Right? I think, I think part of it has to do um, I don’t want to say 

that 

early stage 

venture 

has kind of a 

bad, 

reputation a little bit, you know, 

not of course, of course not because with ten one 10 of course.

Right. you’re 

not 

contributing to it. No, but I mean, I think maybe It’s just kind 

of, 

I think people that, you know, have, uh, I don’t want to say a significant capital conceptually. They just think of, you know, they, 

they 

don’t 

really 

think 

about 

the 

early 

stage 

investing. 

I thought is it? I thought maybe it was just small checks, 

It’s smell. Yeah. Well, it, it, it doesn’t solve a capital allocation problem in a significant way.

Right. 

And I also think that, you know, it’s, you have to have the right kind of investment horizon focus 

for 

it. Right. 

Um, you know where you’re talking about, you know, liquidity horizons at a minimum, 

let’s 

say 

a five 

years. 

in Best 

case 

scenario, 

right? 

Maybe 

even 

decade. Right. 

So, 

so I think we have, we don’t have enough exposure.

We have virtually very minimal exposure to that category at the same time. You know, it’s interesting when you look at the market today, at least we, I think about the market and the venture market, 

and you 

look 

at 

the, 

kind 

of the 

risk 

reward 

ratios 

in 

the 

market, 

Right? we talk about, it. we can talk about asset classes like the public markets or the real estate 

markets, 

or, 

you know, the bond markets are everything.

Even the private equity markets, right. Um, you know, asset prices are at 

an all 

time 

high 

today. Right. And, um, and it’s, it’s 

it’s 

hard 

to 

make 

it, it’s 

hard to 

invest. 

Let’s 

say 

today, 

it’s hard to invest today. Yeah. It’s difficult to invest today. It is. And, you know, and I think that, you know, so my, my feedback, or my, obviously I’m spending my own, time, I spend my time on it.

Right. But my feedback is, you know, I think, I think there’s still a lot of attractive investing in the early stage category. Right. Because evaluations have not. Really creeped up that much as, as much as the, the, you know, the rest 

of 

the 

venture 

market, 

conceptually. 

Um, and uh, so, you know, and also coupled with that, it’s getting harder and harder and harder to get into these transactions.

Right. There’s just more and more competition. So those pro-rata rights are just more valuable than ever. And a lot of the people that invest even with us, and I’m sure with you, you know, they look at it as just like, you know, putting a stake in the ground, right? They’re like, look, I want, to be able to, I want to have a pro-rata right 

to participate 

these transactions.

Um, and, and do you get involved at all in the philanthropic side of things? 

Yeah. I do. I’m, I’m, I’m involved. I mean, you know, as much as I can be. Um, but, um, yeah, I’m, I’m, I’m involved primarily with 

some 

of 

our 

educational 

activities. 

So 

that’s great. Uh, 

 Uh, 

you should tell the office about this great stage.

That’s early stage investing. Um, 

well, 

they 

don’t 

want, they 

don’t 

want 

to 

invest with 

me, 

they might wanna invest with you 

with you  money. Okay. They, they, 

they 

only 

want invest 

with 

successful 

people. 

Okay. 

Uh, Derek said that you’re the most modest self-deprecating person. I said, well, that that’s not what I need on the podcast. 

I need 

some hype here.

Um, what about, uh, you know, where should I go? Watertower? W where do you think? W where’s my question go? Uh, 

what 

you wanna 

talk about? 

Um, that’s a good question. 

we talked about, 

the deal. we 

talk, we talk about water 

tower. 

talked about Derek. We can Tell we 

can 

talk 

about 

Maybe 

the other points 

you had numbers, like advice for 

entrepreneurial advice 

and 

stuff 

like that.

And 

then personal 

stuff. 

don’t know 

what else 

do you 

I want to cover. 

Yeah. 

Uh, 

Okay. So, 

uh, Let me just, so you’re from LA, you went to UCLA Anderson 

and you know, what advice you have for young folks today? 

Well, it’s kind of funny actually. I’d say, I’d 

my 

first 

piece 

of 

advice 

don’t work for a 

VC 

know, 

how 

can I 

say that?

How 

can I say 

that? 

I know you want 

them 

to go through the 

blood, sweat and tears of, 

 yeah. Well, I just think, you know, I think, I think that, um, you know, it’s kind of interesting. when I went to UCLA Anderson, Um, and they characterize themselves as an entrepreneurial, focused school. Right. And granted, this was a long, long time ago.

Unfortunately, 

I went 

but, um, and I, and and they’ve drastically transformed themselves. 

since then, But you know, what’s interesting is, you know, at the end of the day, most of the MBAs there, we’re not going into 

entrepreneurial 

careers. 

Right. 

They were going to more traditional careers and, you know, there’s all different kinds of reasons for that.

You know, obviously it depends on 

everybody’s 

personal situation. 

Um, but yeah. you know, my view is if you asked me, what’s made me a good investor, what’s made me a better investor. It’s really just my experience. Right. and, and I think that that kind of experience as you’ve had as well you know, being a founder and living that That, type of day-to-day and everything, you just, you can’t, learn it yeah. from 

the 

outside. 

Right. and, we always, kind 

of 

joke with our 

founders 

that 

we can 

tell 

you everything 

not 

to 

do 

Right. so I think, you know, I, that’s just kinda my view on it, I think, you know, if I’m giving advice to, a MBA students, is that. You know, you could argue now is, is, is one of the greatest times in history, right? To be, to be able to, to start something, um, there’s capital, you know, people are very focused on the category and you know, not nothing you’re starting a business for a lesson because obviously you’re not right.

You’re starting a business 

to 

have a 

successful outcome, 

but 

I think it’s a very 

valuable 

thing. 

Right. So that, that, that’s kinda my advice, uh, advice to people. And then the other joke, I always say, you know, on the, on the entrepreneurship situation. is 

that, 

in 

terms of 

this 

stuff, 

is 

it, 

you 

know, nobody, 

nobody 

really, 

knows anything.

Right. It’s, 

it’s kind of the joke, right? I mean, I could sit here in this room and try and convince you how smart 

I am 

and everything, but I don’t 

know anything. 

Okay. I don’t know anything more than anybody else. And I think it’s an important lesson, right? for people, you know, in terms of, you know, especially people starting companies and things, you know, it’s 

like, 

do you know, it’s just stay focused on what you w what you think 

is right.

You know, you’re going to hear opinions on everything from other people on the whole thing. It’s like, You gotta, you gotta stay focused and do what you think is 

right. 

Um, 

and, 

uh, 

cause nobody 

really 

knows 

anything. 

Yeah. I, I sometimes like I need to go lock myself in the closet and think for myself. 

Oh, a hundred percent. Yeah.

It’s very difficult. Well, that, that goes back to my a, that, that, that’s why I’m not 

social 

media. 

or anywhere, you know, I’m, I’m, I’m, 

I’m 

private 

person. 

What about, what about, is there anything going through that journey that you can pinpoint when you’re talking to entrepreneurs about what not to do, or like some of those big lessons you had from going through your own entrepreneurial journey?

Yeah, I think it’s a, that’s a good question. Yeah. I think, I mean, honestly, it’s situation specific, right?

but 

I I use the term and I try to live by it myself as well, which is, you know, it’s it’s always easy to be busy for 

busy 

sake. 

Right. It’s always easy to be busy. you know, you need to kind of just, you know, it’s one of those funny kinds of things.

Like I, I use the term 

that 

it’s okay sometimes just to be, do absolutely nothing. Right. You know, in the sense of that, you just, just do nothing. I mean, and I always say like, you know, it’s 

like 

sometimes if you don’t know what to do or you, you know, just, just do 

nothing. 

Yeah, Right. Kind of thing. And, and things will you’ll hopefully a clarity, more clarity from that than being busy.

So I think, I think a lot of entrepreneurs. And rightfully so, you know, especially when it comes to things like fundraising and stuff. I mean, it’s just, it’s, you know, th th they’re, they’re wasting a lot of time Right wasting a lot of time. And so we, 

We want to layer focus on to these, to these companies, and make sure that they’re, you know, and obviously work with them to figure out what that focus should be but make sure they’re focused 

on. 

Value added 

activities 

and 

they’re 

not 

busy 

for busy. That’s really good. Do you live that? Are you able to do nothing?

I do live that actually Yeah. Yeah. 

Can, you can 

ask, 

you can 

ask Derek about 

that. 

I think, 

I think 

it 

probably 

annoys him a little bit, but I think, you know, I look, I think, like you said before, like sometimes you need to go away and be by yourself and think, you know, it it’s in this business it’s difficult. Right. I mean, you’re, You know, you’re being pulled in so many different directions.

You’ve got you’re fundraising. 

You’re, 

you know, 

you’re, you’re, you’re 

looking at new opportunities. You’re. Working with existing portfolio companies. You’re raising capital. I mean, it’s it’s all over the map. Right. And I think, you know, obviously the founders are in that same situation, so yeah, you need to kind of just have a very kind of balanced perspective.

You can’t take every meeting, you can’t take every 

call, 

you can’t 

do that. And, and, you know, and from my perspective, I want to, I want to make sure that I’m focused on value creation for the portfolio 

companies as 

well. 

Right. Um, and I want to make you, so I want to 

make 

sure 

I’m 

focusing 

my 

time 

in there. 

their time properly. 

Yeah, but that’s, I think where I run into the most problem is there’s so many things I could do and, and they asked me, can you make this, can you do that? And there’s so much to do. And then I want to do it all. And I, can’t not be busy. 

I agree. I agree. And I, like I said, it’s a fine line. You know, I mean, obviously you want to be, a, like I said, look.

I mean, we’re, we operate like a startup here, we’re available 24 seven to our companies, you know, we’ll, we’ll do whatever it 

takes, 

right. 

For 

our companies. 

Um, but you know, at the same time we got uh, You know, we got to make sure that like, what they’re calling 

us for 

is a 

value 

added 

activity. Yeah. Yeah. Derek says, I should ask you about your piano playing. Is that part of the doing nothing or does that count as playing the piano? 

don’t know about that. 

I don’t know 

why 

Derek would bring 

that 

up.

You know, I, Derek would bring that up, but no, but yeah, so I, I started playing the piano. I don’t know what it was about. Uh, I played as a kid a little bit but about maybe it’s been a decade 

or so.

Um, of being just focused. I have this kind of long-term horizon commitment in my life where I. Uh, look at things I’m like, okay, fine. So I’m going to start 

this project 

and I’m going 

to 

do 

it 

for 

the 

next 

15 

years, 

and see 

what I can 

get 

right. I can accomplish. So, 

yeah, so I’m a whatever. I mean, there’s not that much, that much, exciting to talk about.

I’m just sedan but a little bit of an amateur, uh, jazz 

piano player, 

and, 

uh, 

you 

know, 

just, just, 

just 

struggling 

every 

day. 

So 

I was gonna say, does it bring you some joy? 

Oh, absolutely. It does. But my family. Has a re like, you know, it’s kind of funny if I said to you, Oh yeah, like your, your husband plays a piano.

You’d be like, Oh, that’s so great. 

It’s so 

fantastic. 

But 

my 

my wife 

and 

kids 

don’t 

feel 

that 

way. 

I think they’re past the point. 

My husband does play the piano 

and I quite enjoy it. I actually, um, 

He’s better than me then.

That’s 

well, let’s talk about your 10, 15 year horizons. What do 

you have 

in your 10, 15 year horizons for yourself 

or for a water tower? 

Well, that’s a good question.

That’s that’s a good question. Yeah. So, um, I think obviously for water tower, you know I mean? Like everybody else, like you guys as well, we’re looking to build a world-class venture capital company you know, and, um, and you know, but I think our focus is we want to stay 

in this 

kind of early 

stage 

category.

Right. We 

think this is where we’re most effective, where there’s most value 

creation 

for 

us. 

Um, 

I would want 

to 

say this 

category, 

how do you see all the good deals in the category? Like, do you go or does I didn’t go to pitch competitions? Or like what, or where do 

why, why 

to you 

deals so good? Your deals are good too. 

are there? Yes. And we should do more of them together.

Um, but yeah. Where do you, how do you stay there? How do you see all the great deals? 

Yeah. Well, I 

think, 

look, 

mean, 

it, like 

I said, 

don’t 

see 

all 

the great deals. I mean, obviously I 

can sit 

here 

and tell 

you 

that, 

we sell like retails, but we don’t. um, we have. You know, like when we have deal our deal 

flow 

comes 

from 

our 

relationship 

network 

right? obviously it comes from our founders relationship network as well that we have, um, and referrals.

And, uh, you know, we also do a lot of, uh, you know, we, we, we, we have kind of like given my affiliation with UCLA we have, a, we, 

we 

save 

have an 

army 

of, uh, 

of 

UCLA 

uh, interns, MBA students that work here. because we have a venture ship scholar program where they 

can work 

as a paid part of the team in the summer. And then they can continue through the year.

with us, and the goal is to learn the venture capital business, and it’s been a 

very 

successful 

program 

for 

us. 

Um, so, 

you know, the reality is, is we, we lean 

on 

that pretty much, right. We, we we, we know that we we only 

have 

so 

much 

bandwidth 

capacity 

right. and we only 

have to spend 

time 

doing 

nothing. 

As we talked about. 

Right. 

And, 

uh, 

that’s be 

time for 

the 

dog 

of course, 

as 

well, 

my golden Ridge, my golden retriever chance.

Right. And, uh, and, uh, so, you know, we lean a lot on them. pretty much. Right. But it’s just, you know, we just find ourselves, we it’s a mixture of obviously covering. All of the, you know, incubators and different things in the marketplace to doing your own thematic, you know, research, um, to relationship building to, I mean, it’s all over 

the 

map, 

would say, 

you 

know, but 

are we seeing the best deals?

I, 

guess 

we’ll 

find out. 

So 

when we, when 

we, 

have our reunion 

uh, session. 

here in five years, 

We’ll see, 

we’ll 

see if we saw the 

best deal. 

ultimate hope it gets you back on before five years go by, uh, Jeremy, anything else? 

Um, 

I think we got a lot, it’s an hour. 

I’m 

good. 

if you’re 

good. 

If you think we can think we have, Oh, 

I’ve got 

to 

hit 

my 

wife’s 

flexible, 

erotic.

too. I got to hit that. Yeah. Otherwise 

I’ll 

be 

divorced. Wait, Jeremy, you have to tell me more about your wife and her podcast, um, which is called the flexible neurotic. And I’m so curious on, cause she’s analyzing her guests and I’m so curious about how she would analyze you. Just tell me more about her 

Well, first of all, was My wife has a podcast, you can find on Instagram at, at the flexible 

neurotic.

Okay. Um, and, uh, the, um, it’s, uh, I always joke that I’m not only an expert in the venture capital business, but I’m also an 

expert 

in, 

uh, 

in 

self 

recreation 

for 

in the 

second 

half 

of life. 

So That’s fun. that’s 

one 

of 

my 

other talents. I’m not sure 

that’s 

going 

to 

bring 

any 

value on portfolio 

covers.

That’s big self recreation for women. Yeah. 

In the second half of 

life, 

So the theme is, so the theme 

you know, 

obviously 

like 

you know, people 

have been, 

of life now, 

I don’t know 

about 

that.

many. I don’t know. I don’t know about that. I don’t know about that. We think of you. as very young, 

many. Okay. You’re young at heart young at heart. Um, so yeah, so she has a great podcast, you know, covering all these 

kinds of 

topics, you know, from, 

um, 

women’s health to nutrition, too. I mean, all over the map really. And I encourage people to check it out. I 

think 

they 

would 

enjoy it. 

Um, in terms of analyzing me, I only get analyzed 

offline. 

with her. So, uh, you know, the, the the joke 

is, 

is 

that 

I’ve been 

successful 

in 

knocking on 

her 

podcast.

but I wasn’t successful and not going on your podcast. 

Well, 

tell her, I appreciate 📍  it. Um, I did listen. I have been listening and you do come up in her podcast. 

I do. 

Yeah, exactly. 

Well only 

my 

best 

qualities 

though. 

outlook. 

Um, well, Jeremy, thank you so much for coming on the podcast on my podcast and, um, I hope to see more of you. 

Great. Thank 

many. it’s 

been great 

and, 

uh, 

hopefully 

we can do a 

deal 

together 

in 

near 

future.

Thanks 

for that. Fantastic. Um, great. Okay, good. We did a lot. 

So I’m free now. Many 

do I do an okay job?