S3 Ep. 2: He Reads Every Slack Message in His Company | James Jiang, CEO Spark Advisors
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The conversation explores James Jiang’s leadership journey as CEO of Spark Advisors, highlighting his calm, measured style. He attributes this to being true to himself and recognizing the importance of steadiness in navigating startup volatility. Jiang stresses self-awareness in managing stress—prioritizing sleep, exercise, and close collaboration with his executive team. A major theme is the challenge of letting go to scale the company beyond a founder-driven model, which requires accepting that other leaders may make imperfect decisions. He notes that leadership has accelerated his self-knowledge, forcing him to crystallize his strengths, such as high standards and hard work, and weaknesses, like moving too fast or hesitating to delegate fully. Jiang values the trust-based dynamic with co-founders Byron and Alex, where complementary perspectives lead to healthy debates and commitment to shared goals. His fears center on not building a lasting institution and balancing rapid growth with upholding company values. Overall, Jiang sees growth as requiring pain and adaptation, with the goal of creating a company that transcends any single founder.
Introduction to James Jiang and His Calm Leadership Style
Or if you're a leader kind of overseeing a project, it's very scary for you to raise your hand and say, hey, actually, I don't think this project makes sense at all.
We should stop doing it.
But that's where you want to get to, right?
And and that only comes from having really, really clear alignment on.
These are the priorities, these are the goals, and this is the vision that we have.
Speaker 2
Everyone loves the story of fast growth.
Very few talk about the psychological cost of holding it all together.
James Jiang is building one of the most interesting companies in the space.
Young backed, scaling fast, leading remotely.
But the part I care about is this, What does it take to carry all of that without letting it carry you?
James Jang, CEO and Co founder of Spark Advisors.
Welcome, buddy.
Speaker 1
What's up Justin?
Glad to be here.
Speaker 2
Yeah, you literally just got here to Miami.
I really appreciate it.
You threw on a sweater, you sat down and you're like a.
Speaker 1
Little bit more professional.
Woke up at 4:00 AM for my flight.
But you know, we're here.
We made it.
Speaker 2
Dude, you were my hero.
Yeah, in more ways than one.
More ways than one.
So we're going to talk about leadership today.
You come across as a calm, measured CEO, not hard to rattle.
Is that who you've always been, or is this something that's happened in the wake of Building Spark?
Speaker 1
Yeah, it's a great question.
I I do think a big part of leadership is being true to who you are.
So I think a lot of this is true to kind of the way that I operate through the world.
I am not going to be the one who is, you know, pounding my chest, whether it's good things or bad things happening.
I tend to be a more kind of calm, measured person.
But as I've grown and as I've built Spark, I've grown to appreciate the importance of that too.
You know, I view my job as a leader as setting the vision and the direction for the company and then being a steady hand through the ups and downs.
Doing a startup, running a business, as you know too, there's constant ups and downs.
If you respond too much to each wave, it just creates unnecessary swirl and distractions for your team.
So I think it's a little bit of both.
It's, you know, I've learned to be more myself, But also I do think that steadiness is really important for running an organization.
Speaker 2
Yeah.
And I think in a leadership position, everybody thinks you have it together, but you and I both know there's some uncertainty.
So who gets some of that uncertainty around you at Spark?
Speaker 1
Yeah, it's a great question.
You know, I think it's really important as a leader to be very transparent with your entire team and kind of tell them your vision, what you expect, how the company is doing.
That said, I think there's limits to transparency.
And of course, you know, for you and I as business owners and CEOs, there are times where we have doubts.
It's important for us to be able to internalise and process that ourselves too.
I'm very fortunate.
I also have really great business partners.
I'm a really great executive team, really great partner.
And so I have people who I can turn to for kind of different, different types of kind of complaints inventing throughout the years.
The Challenge of Letting Go as a Demanding Leader
How do you stay so calm when a lot of the time your team is looking to you for signals?
Speaker 1
Yeah, it's a great question.
Look, I think it's, I think it's really important to know yourself and to know kind of what triggers you have.
I can definitely tell you you've not seen me lose my cool.
I don't think so at least.
But there are times when it happens.
But it's important to kind of know yourself and know kind of when those things might be happening and, you know, have your own ways of dealing with it.
For me personally, when things are really stressful, it's really important to, you know, manage the things that are controllable, right?
Be very, very close to at least my executive team, you know, keep them in the O and keep them in the know and work through these tough decisions with them.
You know, personally, it's, it's the basics.
It's making sure that I'm getting my sleep and my exercise, making sure that I have the temperament and kind of the energy to make these good decisions.
Yeah, but it's not easy.
There are definitely times where it is very stressful and it's on all of us as leaders to figure out what's the right outlet for working those through.
Speaker 2
I have not seen you lose your cold, but are there people on your team?
Speaker 1
There will be one day.
Speaker 2
Or or do they see a polished version of like you kind of like losing it a little bit?
Speaker 1
Yeah, I, I think another lesson for me in leadership is figuring out what is the right way to communicate and kind of express your expectations and where you think things are with different people with different styles.
And I'm trying to kind of balance if, if you ask some of my Zechatism, they'd probably tell you that I'm a pretty hard leader at times.
Maybe it's like a little bit of my, you know, strict upbringing that I had with my, you know, strict, you know, first generation immigration, immigrant parents.
But, you know, I, I, I tend to be pretty demanding when it comes to my expectations.
I tend to be, I tend to have pretty high standards when I see the work of kind of our team and, and they're, you know, they're productive and they're unproductive ways to channel that for me, it's kind of finding the right balance and figuring out, you know, what is the message that each person needs to have.
Speaker 2
So it's funny because you remind me of like what it's like to see your parents and yourself, and that comes out more.
Speaker 1
Deep, I know.
Speaker 2
That comes out more on running a business than it does like, you know, trying to be a a good dad for my kids.
I'm like, man, I just sounded like my mom just said, oh, that's crazy.
How Leadership Accelerates Personal Growth and Self-Awareness
But but seriously, what fears do you have growing a company this fast?
Speaker 1
Yeah, yeah, I mean on, on, on the parents piece, I think a lot of what humans do is a, you know, overcorrection to, you know, historical traumas they've had in childhood.
And so I totally resonate with that.
I think fears, I think sparks is at a point where I want to grow a spark into a real institution.
And you know, we see a lot of agencies that never kind of grow beyond just the founder.
And it is a very kind of relationship, founder driven business.
And I think a lot of the great agencies out there, they are kind of led by these like singular forces of nature, you know, these, these, these CEOs, these principles who everyone knows and everyone loves.
Everyone has this relationship.
And one of my things that I'm working on is, you know, how do I have spark grow into things, grow into something that can transcend even me.
And the last several years especially, it's been this constant exercise of, you know, I want to be close with every one of our partners.
I want to know everything that's going on in the company.
I want to be involved in every decision.
I'm learning how to kind of let go of that in the spirit of scaling this into a real institution and not just a, you know, kind of founder LED agency.
And so my fears are kind of twofold. 1 is it is really scary letting go.
And I've gotten coaching from mentors of mine and even some of our own executive team that hey, in the spirit of scaling the business, I have to let our leaders run.
And that is going to at times lead to our leaders doing things that I disagree with and lead to kind of bad outcomes that I don't like either.
But I have to be willing to, I have to be willing to accept that.
That's one fear.
I think the other fear is simply me not letting go enough and me not letting the company grow into what it could be.
I see so much potential for us and in order for us to get there, I have to constantly be, you know, letting my job evolve as as as as well.
Speaker 2
Has leadership made you more like yourself or less like yourself?
Speaker 1
Also very good Christian.
You're getting me very introspective here.
I, I think especially with the demands of, you know, building this business that's growing so quickly and every single like literally every single day having these ups and downs, I think it forces you to kind of crystallize your knowledge of yourself really, really quickly.
You know, some learnings about myself, some learnings about how I operate, things that I like, things that kind of trigger me.
Those have come much, much faster.
And my kind of frame is I've been building Spark for five years.
I've probably learned you know decades worth of things about myself and and you know how to motivate myself how how I tick over that short time span.
Balancing Rapid Growth While Upholding Company Values
That's great.
So you're young, you're VC backed, and you're scaring the pants out of some of the big boys that have been in this business for a very long time.
So do you feel that you you might be afraid of building a company you're going to grow to hate?
Speaker 1
Also very good question.
Like I, I, I don't know what other people think of us and I, I that that's not the big focus area for us, but I love your frame, right?
It's one of the things I most enjoy about building a business that's growing so quickly is every year changes.
Every year my job description changes.
What I tell every new hired joining Spark is they should also expect their job change pretty meaningfully every year.
That's the nature of a business that's, you know, doubling or more than doubling every year as well.
And you're right, you know, as, as we scale kind of kind of what we were talking about earlier, I have to learn how to let go more and more.
One thing I do believe is, you know, a, a, a business is in a lot of ways an expression of the founder, but the founder has to kind of be able to evolve themselves as well.
You know, one of my fears is not getting that balance right of, you know, empowering the right leaders while also, you know, not imposing those standards and making sure the company is still kind of, you know, operating by the values and by the standards that we have as well.
Hiring Strategy: Missionaries, Mercenaries, and Right Seats
Yeah, What I've learned in leadership is the most important piece is getting the right people on the bus.
And you and I've seen this, you've moved some people around in the different departments.
They've moved over here to over there.
You didn't let them go.
They just moved positions because maybe they outgrew it or you needed them in a different place.
And that that comes with scaling.
So what part of scaling is exciting from the outside, but maybe like is very overwhelming for you on the inside?
Speaker 1
Yeah, yeah, I I think one, one of one of my favorite parts of the job is finding that perfect match between, you know, what the business needs or even what a partnership needs and the right person.
Some of the most rewarding experiences for me have been finding somebody who, you know, might never have even considered working for a start up before, you know, never really considered themselves working in tech and just finding the perfect role for the Met Spark and just seeing their, you know, immediate impact from day one.
And also seeing this person's kind of, you know, conception of who they are as a professional and their careers to evolve as well.
That's been the most exciting part.
And the most scary part is also knowing that, you know, this is a journey with with, with, with a lot of kind of, you know, twists and turns along the way.
And part of that means that not everyone's going to be along for every step of the journey as well, right?
And so sometimes it might be, you know, this person is outgrowing what they can do at Spark.
And, you know, I love that.
And, you know, they can move on and find another success.
Part of it also is, you know, the business that Spark changes too.
And you maybe we need a leader who's, you know, seeing us go from 10 to 100 instead of 0 instead of 1 to 10.
And so, you know, being very clear eyed about those, those, those moments and making sure that everyone is in the right place is, you know, it's both really rewarding, but also really scary sometimes and really challenging.
Speaker 2
Oh yeah, we call them HPM alumni when somebody moves on.
But for the most part we've been able to keep people there using AI to kind of supplement their business without having to scale as fast as as some other companies might be doing.
But you've had great success so far, but you're also beholden to some investors.
So what does that pressure look like for you as a leader, and how do you carry it?
Speaker 1
Yeah, great question.
I'm very fortunate to work with very, very supportive investors and, you know, their whole model is, you know, back extremely early stage companies with, you know, big, ambitious ideas and really just take a bet on the founder.
And so, you know, our first semesters backed us when it was just me and my 2 business partners in a spreadsheet or a, a, a, a, a PowerPoint presentation.
We had no agents.
We're not licensed.
We didn't know how to get licensed.
Frankly, we didn't understand how the industry worked.
They're taking a bet on us and they're taking a bet on, you know, this is a very, very big kind of unsolved problem with the Medicare.
We don't know what the shape of the company's going to look like, but you know, we believe in these people to, to help us get there.
And that's been kind of the nature of the relationships that that we had with our investors.
They, they're super supportive.
They've seen companies go from zero to, you know, IPO and beyond, and they see what it takes to achieve greatness at that scale.
At the same time, they recognize that the company won't be where it is today without the founders.
And so it's been this right balance of helping us to increase our level of ambition and kind of, you know, imagine an even bigger kind of, you know, vision and outcome that we can then, then, then we can believe in ourselves to do while also, you know, making sure that, you know, the founder gets support and the founder has the kind of the room to run to, to exceed against that vision.
Navigating Co-founder Dynamics and Managing Ego in Growth
What is growth exposed in you that you don't think success alone could have shown you?
Speaker 1
Yeah, I'm a big believer that in order to grow, you have to go through, you have to go through pain and and building a company.
It certainly evolves a lot of pain and it teaches you things about yourself.
You know, it's funny, like you, you, you know, you started this conversation with, with saying that, you know, you, you find me to be a very kind of calm and steady hand leader.
I don't think that my friends who knew me, you know, 10 years ago before starting Spark would have necessarily said that.
And so there are there are these things that kind of come up as you go through these wraps of hardships and pain and that that's part of the joy of it, right.
And I think the thing that you know, all of our partners, you know, all of our team members sign up for as well is, I mean, hopefully Spark is going to be a place where you can grow much faster than could grow anywhere else.
The part of that means you're signing up for the pain on the journey as well.
Speaker 2
Yeah, so I've had the honour of meeting all three of the cofounders.
You have Byron and you have Alex, and seeing you guys in the same room these days is very difficult, but you can obviously see the dynamic that you guys bring to an organization like this.
It all starts at the top.
Can you kind of dive into that dynamic and what works?
What's the magic sauce that's that's happening there?
Speaker 1
Yeah, yeah.
We, we're very lucky that it works like we, the three of us did not know each other that well when we decided to start Spark.
And it was it was the first year of COVID.
And so we didn't even spend that much time together in person when we're, when we're thinking about this idea.
But it turns out we ended up being very complimentary.
For anyone who has met Alex or Byron, I think you'll quickly recognize that, you know, we're all very, very different people with very different skill sets, very different kind of philosophies, very different perspectives that we bring into the business and bring into kind of how we relate to each other.
I think the thing that's really worked for us is despite all those differences, I'm having this kind of shared sense of trust.
What that means is, you know, we're all lined, we're all incentivized around the same goal.
We all believe in the same vision.
We all kind of trust each other to be, you know, hard working, ethical people who are going to be good stewards of the business and the organization, the the parts of the organization they run.
And I think that's been the magic like we, we get into pretty strong disagreements, but I think, I think I think in a very healthy way, right?
It's a, I, I, I think the, the alternative where it's, it's three business partners who all kind of think and feel the same way.
I think you would end up having a lot of blind spots.
And the, the most story we've had is just getting into these, you know, very vigorous, maybe vicious, you know, debates and arguments and then ultimately, you know, deciding, hey, we all care about this business.
It's, it's all of our babies.
And once we once we decide on the path, we just commit to it.
Speaker 2
It's hard for me to imagine that because you guys are all brilliant, articulate individuals.
So is there anything that you find them protecting you from?
Speaker 1
Yeah, going back to the, you know, the the the point on trust, I think the nice thing about business partners who you can really trust are, you know, there's always things that are going well and poorly in the business.
It is so valuable having you know, business partners or executives who you can trust.
And you know that there are things that you know, there are, there are problems that they're working through, but you can just fully trust that they can handle it.
And you know, a lot of what we've gone through in the last five years at Spark has been at any given time, you know, the parts of the organization that I oversee or alliance or buying overseas, there's always going to be challenges and opportunities.
And it's, it's amazing having this feeling that you know, you have this partner and whatever the challenge is, you know they can, they can handle that.
Speaker 2
What do you think that they see in you that you might not see in yourself?
Speaker 1
Wow, That's a very deep question.
It's a very great question.
And the nice thing is they can, they can definitely see my strength and my weaknesses.
I think they, they, they see, I think one thing I bring uniquely and I think one thing that is the job of any CEO is to be relentless about pursuing that vision and having the standards to get there.
And one thing I can pride myself in is being the hardest working person, the hardest working person in the company, Never asking someone to do something that I wouldn't do myself personally and really trying to kind of push the frontier all the time.
I think they've been able to see a lot of the a lot of the blind spots or maybe the weaknesses of that approach as well.
They've seen times where, you know, maybe I can I can move too fast or too aggressively.
Maybe I'm not giving some of our, you know, emerging leaders that the full reins kind of run and kind of show what they can do as well.
You know, as we've kind of talked and as we've grown animal of the business, you know, we've had a lot of great conversations like that on, you know, what are each of our own personal blind spots.
Speaker 2
So this business has no shortage of ego, you know, and in any level, how do you as founders balance that without ego getting in the way?
Speaker 1
It's a great question.
I think one thing that's been very, very core to our ethos and our mission from day one has been I guess this balance of ambition with humility.
And I think a lot of that comes from, you know, my temperament, how I was raised.
I think a lot of, you know, Alex and Byron's philosophies as well, even small things like we, when we first, you know, worked with, you know, agencies and agents, we never called people down lines in the relationship.
You know, we always wanted to believe that, you know, Sparks job is to be in the background.
Spark's job is to provide, you know, really excellent technology, real excellent service to help our partners to do what they do best.
All these little decisions on, you know, having our partners, you know, brands be front and centre, you know, really highlighting their wins, you know, really viewing ourselves as, you know, working in service of them.
That's just been a big part of for Youthos from day one.
I will say, I think that part like almost just comes naturally to me.
And you know, my kind of greatest division of, of success for Spark is, you know, we end up being this infrastructure that helps hundreds of business owners to succeed beyond their wildest dreams.
And through doing that, you know, help all these brokers and help the all these consumers as well.
So that's of all the challenges that we've had is it's never been that hard for us to kind of stay true to that ethos.
Speaker 2
Yeah, yeah.
The Challenge of Aligning Brilliant Minds in a Fast-Growing Company
What's harder, finding brilliant people or staying aligned with them?
Speaker 1
Yeah, I've been thinking a lot about the the different types of players you want on your team as you're building a company, especially a fast growing company.
And one frame I like using is kind of the the the the missionaries versus the mercenaries.
And I think there is a role for both.
And you're starting with the missionaries.
You know, when we're just starting out, it was very hard to recruit any talent to come and join us.
You know, we're just, you know, three guys with an idea.
We weren't even licensed as agents, I think.
Speaker 2
You had APO box only at that point.
Speaker 1
We had only APO box for probably the first three, 3-4 years of, of, of, of doing this.
And so the people who we attracted were missionaries.
And, you know, some of them already had this passion for fixing healthcare and helping the elderly.
Some of them, you know, gradually grew to kind of, you know, love our mission.
And that's super, super important.
And those people?
You know, those people go to go go to battle for us in any given day.
We also have people who, you know, as you've scaled, maybe have the more polished resumes and kind of the experience in the skill set.
And I guess I, I wouldn't frame them quite as just mercenaries, but it's people who have these really, really talented skills.
But then it's, you know, it's, it's a question of how do you, how do you find the right kind of position for them?
And look at the, the counterpoint of what I said earlier on, you know, the, the most rewarding thing for me is finding the perfect role for the perfect person.
The thing that's also really challenging is sometimes we'll have people who have this amazing talent and just figuring out where do you kind of slap them in, especially as the business evolves.
I wish that we had to fully figure it out, but that's that's part of the challenge of, you know, running an organization with a lot of people with a lot with a lot of different talents as well.
Speaker 2
Yeah, we call it right people's right seats.
And what we do is we evaluate that every 90 days because things can happen very quickly.
So you might say, wow, this person is really scaling up in, in this level and we want, we need them over here now.
Sometimes you have right person, wrong seat.
Sometimes you have wrong person right seat.
You know, and I've made the mistake of firing people and firing the entire position.
Yeah, waiting a couple years to redo that.
And that's a mistake.
Yeah.
So but it all go ahead.
Speaker 1
I mean, I love what you said about every 90 days too.
I think part of it is also calibrating what is the right frequency with which you make those reevaluations.
Because if you're moving too fast and maybe the market and maybe the environment, maybe the strategy is moving.
But if you're moving too fast without bringing everyone along, then you create this perception of, you know, whiplash and swirl.
And that can be very demotivating for people as well.
At the same time, I think waiting too long is also a problem in a, in a different way too.
So whether it's 90 days, 180 days, you know, every year, getting that balance right for the stage of the company is also very hard.
Speaker 2
Yeah, it lines up great as far as the year is concerned because our quarters, you've got Q4, which is AEP, that's our season and then you've got Q1 OEP and then Q2 lock in, Q3 lock in.
Strategies for Building Trust in a Remote-First Organization
But even in Q2, that's when you would kind of go into vacay mode.
You get to rest up a bit and then Q3 you're gearing back up and you've got a great culture.
You know, you guys do retreats.
I see it.
But how do you build trust both at the leadership level and you'd mentioned you guys didn't really know each other that well and then look at you now.
So how did that trust come about?
And then how does that get down into your organization?
Speaker 1
Yeah, it's a great question.
I'll start with the basics.
It's just simply spending a lot of time with each other and talking loud.
And you, you kind of alluded to this, but we are a remote first company.
And so, you know, all of our employees work primarily remotely.
You know, we now have kind of satellite offices and so we do get more in person time.
But, you know, benefit there is you can recruit people from all over the country and you have this, you know, what much wider base of talent the potential downside is.
It's it there.
There's a risk of, you know, feeling disconnected from your teammates and from your work.
And sometimes, you know, messages get lost in, you know, text or in e-mail or in kind of messaging services.
And so, you know, one of the basic things and one of the cultural things that we're still trying to push, especially as we scale, is there's a lot of value in just picking up the phone and calling somebody.
And there's a lot of trust building.
There's a lot of alignment.
There's a lot of just really understanding someone's perspective that you can't get through through without just, you know, that that live interaction.
So that's a big part of it.
Another big part of it, and your big credit to Alex by my my Co founder for really pushing kind of this cultural norm throughout our company is being very, very explicit about who owns a initiative or deliverable or KPI and imbuing that person with the trust.
But with that also comes, you know, let's make sure that we're reporting on it so we can actually understand how we're doing.
Let's make sure that that person, they're empowered with owning that deliverable, which also means they're empowered to kind of ask for help and, and bring people along, bring, bring people along to, to, to support them on that as well.
So kind of having that very, very clear sense of, you know, who owns what, giving people responsibilities and then kind of following through, making sure they have the support for it and making sure that we all kind of have alignment on, you know, are we, are we getting this, getting this done or not?
Speaker 2
Yeah, So you're remote.
First you were in New York City.
Now you you just bought a house in Lake Tahoe.
Congratulations, by the way.
Amazing.
That's culture shock.
So you're running this company virtually remote because I don't think you have any employees in like Tahoe.
You haven't.
Speaker 1
Not yet dragged anything out there yet.
Speaker 2
So how has that made you as a leader?
Has it shifted anything in you?
Has it made it better or just different?
Speaker 1
Yeah.
To be honest, not much has changed and the reason is we are already running this kind of, you know, remote, remote first company and culture.
We have already been investing in your regular kind of in person gatherings of, you know, all of our team or different functions within our within our organization.
You know, a lot of our interactions we've already figured out how to do virtually.
But again, the big challenge I think is reinforced as you know, you know, me, me moving out of New York is I think less important than, you know, roughly doubling the number of team members we had in the last year.
It just makes the communication and the live communication, getting in the phone, getting in person, just that much more important.
Speaker 2
Yeah.
So is there anything about distance that gives you more or less than proximity?
Does it change the way you operate?
Speaker 1
I guess getting personal, getting personal, living in the mountains in Lake Tahoe is very, very different from living in Manhattan or Brooklyn in New York City.
You know, I think people people get used to a new environment shockingly quickly.
Like I thought it would be a bigger kind of personal cultural shock than it actually is.
Maybe the issue is I'm still working 12 hours a day and so it doesn't really matter if if I'm in New York and.
Speaker 2
You're still walking very fast.
Speaker 1
I'm still walking very fast.
So yeah, it hasn't, it hasn't been that big of a difference.
You know, I'm, I'm in New York City probably once a month.
I'm still seeing my team in person.
If anything, I might be seeing them more frequently in person just because we're making more of an effort there.
But yeah, I think for me, one of the big lessons is you can't adapt to these new things pretty quickly.
But it's important to be intentional as these environments change.
What Remote Leadership Exposes and How to Build Culture
What does remote leadership expose that office leadership can hide?
Speaker 1
It's a great question.
Well, it's hard for me to fully answer that because I've never really experienced, you know, a large office office culture for a large, fast growing company.
I'd say with remote, you just have to be a lot more intentional about the kind of cultural practices you build.
One thing I'm super, super proud of is if you interview any of the, you know, new sparkies joining our team, you know, you know, one month, two months, three months, and they'll all talk about how, you know, welcoming and warm the culture is and how and, and their teammates are.
And that doesn't happen by default.
You know, it's very easy if you're a remote employee joining a, you know, 100 person organization and you know, you're working from home and there's no one who's even in your state, it it's very easy to feel isolated.
And I think we've been very intentional about kind of creating this very collaborative high trust culture.
And so when someone's coming on board, on coming on board with Spark, you know, they're all hearing from me and from a business, from my business partners about, you know, our strategy, our vision, our culture.
We're very deliberate about, you know, having them have onboarding buddies and having people kind of deliberately reach out and kind of you guide them along the way.
I would assume it's, it's much harder to kind of, you know, roll out that culture virtually, but requires that deliberate care.
But the benefits are, you know, you can give people flexibility and you can end up, you know, opening up a lot more talent to join your company too as as well.
Speaker 2
What breaks first in a remote, fully remote company?
Is it culture, is it standards, is it communications?
Or is it things like accountability?
Speaker 1
I think it's all of it, all, all, all of it is, is very, very important.
Yeah, I think that the the, the, the number one thing I think you miss is some of the really important, but, you know, unstructured, more spontaneous conversations and just the context sharing as well, right.
And I think a lot about how, you know, sometimes we'll have a small squad of people go off and kind of work on what I think is a little bit more of a rabbit hole Y project, in part because they don't have the kind of the shared the shared business context.
And I think so much of leadership in running a large organization is to give everyone as much of the shared context as possible.
That was really, really easy when it was just myself, Alex and Byron.
And we're just talking every single day.
It's really, really hard with a large company where, you know, half your company's new every, every, every single year.
And I think in that environment, it's a lot.
It's a lot easier when you're all in the same office and you're just overhearing conversations and you know, the the engineering team is hearing about some, you know, some, some sales deal from the sales team and the marketing team is hearing about our technology from another kind of team.
It's harder to kind of have all of those spontaneous interactions when you're remote.
Speaker 2
Yeah.
So how do you build that emotional connection and urgency when everybody's kind of spread out?
Speaker 1
Yeah, one of the best pieces of advice I've gotten that I will admit I've not fully lived on yet is it's just important to be very, very repetitive.
And so much of leadership is, you know, setting that vision, getting the vision and getting the big ideas right, but then just being unafraid of being repetitive to the point of, you know, thinking that you're boring and just kind of sharing that through with everybody.
And so, so much of, you know, what I spend my time on and what our leaders think not spend our time now on now is going away from, you know, individually trying to be the best problem solver or salesperson or, you know, what whatever it is into.
How do you bring everyone along?
How do you kind of how do you share them, share with them all of the contacts in that vision as well?
Speaker 2
Yeah, we call it the rule of seven.
You got to say it seven times and it's annoying.
And so we'll be in a meeting and I'll be like 3, you got four more to go.
You know, because we do, we often get frustrated when our team, our agents, our agency partners are like, man, we we've said that like at least three or four times and I'll hear my team say that I'm like, yeah, you've got three or four more times to do it before it like locks in.
So totally get you on that.
As far as your, your stance, like even online, your messaging and your presence is pretty clear.
Like you're very articulate.
You put out the right messaging.
How much of leadership is really about reducing that chaos and turning it into a language that everybody can understand?
Leadership's Role in Reducing Chaos and Communicating Vision
I think that is probably the majority of the job.
And I appreciate you saying that.
And I think there's all these ways that we can, you know, spark and, and I can still do better at kind of getting that message out.
But I, I do think that's, that's almost all the job.
And again, you know, I, I am currently learning how to evolve from, you know, personally, you know, spending, you know, all the time with the partners and doing recruiting, kind of doing all these things into recognizing that my job is to set that vision and just repeat that over and over again.
Whether that's with agency partners, with insurance carriers, with the industry at large, with their own employees, It is really important.
And there's always room for us to improve there, too.
Speaker 2
When founders get that wrong, what kind of damage could they do to the company?
Speaker 1
I mean, we're, we're going through right now to some degree, right.
It's, it's, it's people not have, well, I'd say the, the other way I think about it is the, the ideal organization is 1, where every single person feels maximally empowered to do, you know, the most productive thing for the business that aligns with their skill sets as well.
And ideally they can do that without getting, you know, very, very explicit instructions.
I think it's a failure mode if the company has to tell every single employee very specifically, you know, what are the one or two things you have to do every single, you know, weekday, whatever cadence it is, ideally it's, you know, everyone is imbued with this is the strategy, this is a vision.
These are our operating principles, these are our norms.
And you know, I now know what specifically I have to do to advance this forward.
That's where we want to get to and, and with spark, with how quickly we're going, you know, there's, there's always this balance of, you know, setting that direction, but also making sure that we are focused on the right things.
And it's very easy as you get bigger, as you get more resources for, you know, projects to, to, to, to, to, to sprawl, right?
And like somebody isn't super clear on what all the instruction, what, what all the most important things are.
And then you'll end up seeing instead of, you know, here are the two things that have to get done this year.
It's here are the 15 things that we have some Commission on.
And we're not quite sure.
And maybe we even forgot why it mattered, you know, two quarters ago, but we're still doing it.
But it's a constant kind of balance and pruning of those things.
Speaker 2
Yeah.
And it kind of goes back to that 90 day loop where you get to re evaluate like what's burning on the stove, what's going on the back and what what comes forward.
And, and sometimes people get nervous when you change, anytime you change something like people get nervous.
So how do you how do you know when to communicate reassurance versus communicate the reality that might make people uncomfortable?
Speaker 1
Yeah.
I mean, I would, I would say one thing I actively try to encourage is every single person at Spark being comfortable with saying and, and, and raising their hands and saying when they think we're doing a project.
It just doesn't make sense.
And it's very scary, right?
If you're, if you're a leader kind of overseeing a project, it's very scary for you to raise your hand and say, hey, actually, I don't think this project makes sense at all.
We should stop doing it, but that's where you want to get to, right?
And and that only comes from having really, really clear alignment on.
These are the priorities, these are the goals, and this is the vision that we have.
Navigating Decisions and Information Overload (Even Slack)
When it comes to things getting messy, because it often does, I mean, we get Intel all over the place.
How do you stop that intelligence from taking over and kind of forcing you to overthink a lot of things?
Speaker 1
Yeah, yeah, it's a great question.
So we use Slack as our internal messaging service and we've had some very real debates.
Hopefully, you know, I don't scare any of the smart people who are saying this about should we just get rid of Slack all together, which like would would sound crazy to so many people at Spark because it's such a big part of our culture.
But I do think that when not used thoughtfully, you can just be overloaded with all of these messages, all, you know, all hours of the day.
And it's, it distracts you from the most important things.
And so this balance, you know, even for me as a leader, some of our execs, you know, joke with me that I read literally every single slack measures that that have in the company.
I probably do.
I, I I read really.
Speaker 2
That is a problem.
Speaker 1
I read, I read fast and I, I work long hours.
But you know, even for me, I, I, I have to start the balance of if you want to get the strategy right, you have to understand what's going on at the ground level.
At the same time, you can't be, you can't be kind of swayed by all of this noise and all of these new inputs that happen all the time.
And you know, for, for our team members, you know, what I say to them is if you're doing the work, like you have all of these valuable insights and that's super, super important for us to all be able to share.
But then we were talking about it earlier about, you know, the 90 day or, or whatever cadence.
You also can't be making adjustments based on those learnings too quickly either.
Speaker 2
Yeah.
Does it scare you not knowing what's going on in the company sometimes?
Well.
Speaker 1
All the time.
Yeah.
Yeah.
Speaker 2
It's one of the things that keep me up at night.
But you know, it's sometimes you just have to.
It goes back to the trust part and people add me into threads or they add me into, you know, a channel and I'm like, hey, could you kindly remove me from this?
Because I don't think I'm going to add any value to this.
And it's no offence to them.
It's just, hey, this is just going to jam up my brain.
So, you know, you got to protect that.
But because you have to make decisions, you know, and I think it was Steve Jobs that says you only have a finite amount of decision power during the day, which is one of the reasons he wore turtlenecks every day because he didn't want to make a clothing decision.
One of the reasons why you and I start wearing black all the time.
But was there a decision as a leader that it looked right on paper, but you knew it, It didn't sit right with you in your gut?
Speaker 1
Yeah, I, the way that I make decisions is I, I do like to get as much data as possible.
And so like 1 balance that I'm trying to strike is trying to read everything that's going on in the company while also not, you know, hovering and disempowering people.
And I'm still trying to work on that balance.
But I like getting as many inputs as possible for these big decisions.
It's also very important for, it's very important for me to sit on it as well.
And there have been a number of big decisions that in, in the spirit of trying to kind of get us to clarity quickly and move quickly, I tried to push forward, you know, let's just decide and kind of move on only to, you know, 3-4, five days later, you know, have, you know, just processing all the, all the data more talking to more people, more kind of realizing that we should, we should go down a different course.
And so the, the other balance that we're trying to strike is when do you want to be decisive versus when do you want to just really invest and get all the people in the room and kind of just spend the hours and the calories needed to get the decision right?
Like one thing that we've been trying to do at Spark is understanding, you know, the calibrating and the magnitude of the decisions.
And for the smaller ones, yeah, move really quickly.
And and for the very big ones, invest in what might feel like the inefficient, you know, in person time, phone calls, you know, phone calls outside of the scheduled meetings just to make sure that it's absolutely right.
Speaker 2
Yeah, One thing that it reminds me of is when you make a decision, you got to live with it, you know, because there's so many times that you rethink stuff and you just got to let it go, even if it's a bad decision.
You know, indecision will kill more time and energy and calories than not making a decision at all.
So that's that's one big lesson that I've learned.
So it reminded me of that.
The Personal Sacrifices Required for Building a Great Company
So we're to our last question here.
We've had that much fun.
And I know you're probably exhausted and you got a thing to go to, so I got to get you out of here.
What have you had to sacrifice for this version of James for the benefit of Spark?
Speaker 1
It's a great question to close on.
I work a lot and I think that to be a business owner, to be a founder, to try to build something really great, you just have to make that sacrifice.
And so for me, I'm very deliberate on you for this chapter in my life.
I want to be very focused.
And you know, besides spending time with my fiance, it's basically just all spark.
And that comes at the expense of, you know, some personal time sometime, you know, some vacation time, you know, working on hobbies, kind of other things.
But I love that too.
And I love being able to be single mindedly focused on just one thing.
I really care about our vision.
I really care about our team.
I really care about us reaching our full potential.
So it doesn't really feel like a sacrifice.
But you know, deliberately I'm trying to clear as much space as possible to focus on getting this thing to where it could be.
Speaker 2
Any last words for anybody listening and watching you?
Anything you want to leave with?
Speaker 1
Agents.
Speaker 2
And agencies here.
Speaker 1
No, I'd just say these are really great questions.
Leadership is, is very, very hard.
I have by no means figured it out.
I think the biggest thing is being willing to be introspective and understand where your blind spots are and understand what it what, what it takes to work well with other people because that's the only way you can scale.
And I just wanted to say I appreciate you, man.
I appreciate you doing this podcast.
Appreciate you know you copying my wardrobe choices and being all black as well.
Speaker 2
You've got great style, man, You've got great style.
James Jiang, Co founder and CEO of Spark Advisors.
Thank you very much for being here.
Thank you for flying into Miami.
You're free to go to your party.
Speaker 1
Thank you, Justin.
Really appreciate it.
Thanks.
Justin's Final Thoughts on Leadership and Growth
The bigger the company gets, the more leadership becomes an emotional job disguised as a strategic.
James made that clear.
Building fast is one thing.
Staying clear, steady and honest while you do it is something else entirely.
Subscribe, leave a comment and send this to a founder carrying more than anyone around them realizes.
I'm Justin Jacobs, this is closed.
You have a nice day.
Speaker 1
No excuses I.
Podcast Summary
Key Points:
James Jiang, CEO of Spark Advisors, emphasizes a calm, measured leadership style rooted in self-awareness and transparency with limits.
He views his role as setting vision and being a steady hand through ups and downs, managing stress through sleep, exercise, and close work with his executive team.
A key challenge is letting go of control to scale the company beyond a founder-driven agency, accepting that leaders may make decisions he disagrees with.
Leadership has accelerated his self-knowledge, revealing both strengths (high standards, hard work) and weaknesses (moving too fast, not delegating fully).
Co-founder dynamics thrive on trust despite strong disagreements, with complementary skills and shared vision enabling healthy debate.
Fears include not scaling the company into a lasting institution and balancing rapid growth with maintaining company values and standards.
Summary:
The conversation explores James Jiang’s leadership journey as CEO of Spark Advisors, highlighting his calm, measured style. He attributes this to being true to himself and recognizing the importance of steadiness in navigating startup volatility. Jiang stresses self-awareness in managing stress—prioritizing sleep, exercise, and close collaboration with his executive team.
A major theme is the challenge of letting go to scale the company beyond a founder-driven model, which requires accepting that other leaders may make imperfect decisions. He notes that leadership has accelerated his self-knowledge, forcing him to crystallize his strengths, such as high standards and hard work, and weaknesses, like moving too fast or hesitating to delegate fully. Jiang values the trust-based dynamic with co-founders Byron and Alex, where complementary perspectives lead to healthy debates and commitment to shared goals.
His fears center on not building a lasting institution and balancing rapid growth with upholding company values. Overall, Jiang sees growth as requiring pain and adaptation, with the goal of creating a company that transcends any single founder.
FAQs
He focuses on controllable factors like staying close to his executive team, ensuring they are informed, and managing personal basics such as sleep and exercise to preserve energy for decision-making.
He fears not letting go enough, which could prevent the company from becoming an institution beyond himself, and also worries about leaders making decisions he disagrees with as he scales back control.
He adapts his message to each person, channeling his demanding nature productively by finding the right way to express expectations based on individual needs, rather than a one-size-fits-all approach.
He finds it rewarding to match the right person to the right role, even those new to tech or startups, but acknowledges the challenge that not everyone will stay as the business evolves, requiring clear-eyed decisions about fit.
They point out weaknesses like moving too fast, being too aggressive, or not giving emerging leaders full autonomy, complementing his strengths such as being the hardest worker and relentlessly pursuing the vision.
They engage in vigorous, healthy debates and arguments, then commit to the chosen path once a decision is made, relying on shared trust and aligned incentives to move forward.
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