[Venture Capital Series] Triaging Growth Challenges in Startups With Brett Browman

Brett Browman is the Growth Operating Partner at Khosla Ventures, where he helps scale transformative tech companies through hands-on growth strategy and marketing. As the first growth hire at both Square and Opendoor and a former operating partner at Andreessen Horowitz, Brett brings deep experience driving customer acquisition and business growth. He’s worked closely with top startups like OpenAI, Stripe, DoorDash, and Ramp, and is known for his tactical, team-focused approach. Beyond tech, he has snowboarded on all seven continents and brings a global, adventurous mindset to company building and culture.

Here’s a glimpse of what you’ll learn:

• [04:25] Why Brett Browman takes a hands-on role in accelerating startup growth
• [06:09] How Brett uses an “ER doctor” mindset to diagnose growth challenges
• [10:28] How new leaders can quickly build trust with their teams
• [12:10] How Square identified their ideal customer profile early on
• [17:55] How mentors influenced Brett’s data-driven approach to growth
• [20:56] Why autonomy and trust are key to innovation at Khosla Ventures
• [25:46] Brett’s go-to AI tools that are transforming marketing and growth
• [32:18] How to measure the impact of both online and offline marketing efforts
• [48:10] Brett’s recommended resources for product and growth

In this episode…

Today’s fastest-growing startups thrive by cutting through noise and building real trust across teams. But what makes a venture partner more than just an advisor — and truly hands-on in the trenches? And in an AI-driven world, do old-school tactics like direct mail still have a place?

Brett Browman has helped scale some of the world’s fastest-growing startups, from Square to Opendoor, by going beyond boardroom advice and working directly with teams. He partners with companies at every stage — building marketing teams, refining strategies, and driving execution. Known for his hands-on, no-ego approach, Brett empowers teams, builds trust, and focuses on fundamentals like ideal customer profiles, key metrics, and product differentiation. His work, including unconventional tactics like direct mail, shows how grounded strategies and strong teams fuel lasting growth — even in a tech world racing toward AI.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Brett Browman, Growth Operating Partner at Khosla Ventures, to talk about scaling startups, hands-on leadership, and what it really takes to drive sustainable growth. They discuss Brett’s “ER-style” triage approach to diagnosing bottlenecks, the role of trust and autonomy in building high-performing teams, and why direct mail still has a surprising impact in today’s digital world. Brett also shares insights on the rise of Generative Engine Optimization, and why mastering the fundamentals beats chasing growth hacks every time.

Resources mentioned in this episode:

• Brett Browman on LinkedIn
• Khosla Ventures
• Visual IQ
• Character AI
• Fireflies.ai
• ClickHouse
• Square
• Opendoor
• Wooden: A Lifetime of Observations and Reflections On and Off the Court by John Wooden
• Lenny’s Newsletter
• More or Less Podcast by Jessica Lessin
• Drive: The Surprising Truth About What Motivates Us by Daniel H. Pink
• The Black Swan: The Impact of the Highly Improbable by Nassim Nicholas Taleb
• Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets by Nassim Nicholas Taleb

Special Mentions:

• Vinod Khosla on LinkedIn
• Josh Payne on LinkedIn
• Coframe
• Andreessen Horowitz
• Ryan Scott on LinkedIn
• Keith Rabois on LinkedIn
• Traba
• Ravenna
• Credit Genie
• Ramp
• Recraft
• Profound

Related episodes:

• “Automation Solutions with Wade Foster Founder of Zapier” on Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on Inspired Insider Podcast
• “[SaaS Series] Revolutionizing Online Forms and Productivity With Aytekin Tank of Jotform” on Inspired Insider Podcast

Quotable moments:

• “We take a much more hands-on role — I get in the trenches like almost a fractional growth leader, actually driving outcomes with companies.”
• “I’m above no task, meaning the most menial of tasks, especially to start, I will absolutely do that.”
• “One of the things that great leaders do is help elevate the people they lead and let their talents shine through.”
• “The number-one way you’re going to win is focusing on the fundamentals and building a repeatable growth engine.”
• “Let your story shine through — people love stories and pictures of people in ads. That’s far more powerful than an incentive.”

Action steps:

1. Define your ideal customer profile: Identify who your product truly serves by understanding their pain points and how your solution uniquely addresses them.
2. Build trust through supportive leadership: When stepping into new teams, focus on empowering others, earning trust, and creating space for collaboration and growth.
3. Track the metrics that matter: Align your team around clear, visible KPIs — such as acquisition costs or customer lifetime value — to drive focus and performance.
4. Explore offline and creative channels: Don’t overlook unconventional tactics like direct mail or podcast ads to stand out when digital noise is high.
5. Master the fundamentals: Prioritize product quality, customer value, and repeatable growth strategies over trendy hacks for lasting success.

Episode Transcript

Intro 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz 00:22

Dr. Jeremy Weisz here Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Brett Brownman of KhoslaVentures.com. You can check him out at KhoslaVentures.com.

And Brett, before I formally introduce you, I always like to point out other episodes of the podcast people should check out. I was thinking, I mean, Khosla Ventures. I was talking to my business partner, John Corcoran, who’s in the San Francisco area. He’s in Tiburon, and he’s like, Khosla Ventures is epic, so you better do a good job. Jeremy.

I’m like, no, no worries. And just to give you an idea, I’m like, what other episodes were cool that people who are interested in cultural ventures, like we’re talking about Khosla Ventures, did early bets on open I, stripe, square, DoorDash. So, you know, some past episodes I did with the Co-founder of Zapier. That was an interesting one. So we’re talking like SaaS that, you know, Wade Foster, we did one with Pipedrive. Pipedrive. I think when I interviewed them, Brett, I think they were 10,000 customers. Now I think they’re over 100,000. So they’ve grown quite a bit. And Jotform is another one I think he talked about. The founder talked about growing over 25 million users.

So just some interesting journeys and stories. And today’s going to be the same so people can check those out. This episode is brought to you by Rise25. At Rise25. We help businesses give to and connect to their dream relationships and partnerships. We do that in a few ways. One, we’re an easy button for a company to launch and run a podcast. You know we do the strategy, accountability and the full execution and production. We also get people on podcasts like Jeremy. I don’t want to do all the work in the podcast, even though I think it’s amazing.

I just want to go on shows and like, cool. Well, let’s connect you with some great shows. Number three is we’re an easy button for a company’s gifting. So we make gifts and stay top of mind for clients, partners, and prospects. Simple and easy and affordable even for staff. So all you do is give us a list of people we will keep in touch by sending them sweet treats in the mail over a period of years. Even so, we call ourselves the magic elves that run in the background and make it stress free for companies so they can build amazing relationships. 

And for me, I found no better way over the past 15 years to profile the people and companies I admire and send them delicious treats in the mail. So if you have questions, go to Rise25.com or email us at [email protected]. I’m super excited to introduce Brett Brownman. He’s a Growth Operating Partner at Khosla Ventures. Khosla Ventures was founded by Vinod Khosla, Founder of Sun Microsystems, and they are a $18 billion venture firm. 

And as I mentioned, behind bets such as OpenAI, Stripe, Square and DoorDash, and Brett previously held the same role, Andreessen Horowitz and was the first growth hire at companies both Square and Opendoor. And at Khosla Ventures, he partners with startups to scale marketing and growth from the ground up. And big shout out to Josh Payne at Coframe. People can check out Coframe to introduce us. So Brett, thanks for joining me.

Brett Browman 03:34

I’m very excited to be here. Thank you Jeremy.

Dr. Jeremy Weisz 03:36

So just talk about Khosla Ventures and what you do is you’re doing that. I’m going to pull up the site so we can poke around.

Brett Browman 03:43

Awesome. So yeah, our role, you know, we’re a multi-stage venture fund. So we invest all the way from seed and idea all the way up to very late stage, like we just invested in leather running Clickhouse, which is a very late stage AI-focused company, and I help companies across all spectrums of life cycle. So again, from your idea all the way up to you’re trying to grow it to like, this is like we’re trying to scale and we want to build a team. And I help with all aspects of growth marketing, go to market, acquiring customers and scaling the business.

Dr. Jeremy Weisz 04:23

You mean you’re rolling up your sleeves?

Brett Browman 04:25

Absolutely. Yeah. You know, the operating partners, a lot of them are sort of later in their career stage. They’re more wanting to do advisory sit on boards. That’s sort of like the traditional role of an operating partner. We take a much more hands on role. Like I get in the trenches like almost like a fractional growth leader, like actually doing work with companies and actually driving outcomes.

Dr. Jeremy Weisz 04:54

I’m going to pull this up too. Right. Is this Clickhouse?

Brett Browman 05:00

Yes.

Dr. Jeremy Weisz 05:00

Yeah. So what does Clickhouse do? This is interesting.

Brett Browman 05:04

Yeah. So they are open source databases that are used by basically replacing, you know, SQL or other databases that you have in the background and then they build products on top of that. It’s large.

Dr. Jeremy Weisz 05:20

Technical.

Brett Browman 05:20

Yeah. Large enterprise.

Dr. Jeremy Weisz 05:21

I’m looking at some of their Clickhouse is trusted by Spotify, Lyft, HubSpot, huge companies here.

Brett Browman 05:28

Yeah, they’re akin to what Databricks calls it, which I think people know super well too.

Dr. Jeremy Weisz 05:35

Yeah, I mean, you I’m we’re looking on the page here. If anyone’s listening to the audio, the portfolio page. I mean, we have consumer and retail, enterprise, fintech, frontier sustainability, digital health, medtech, therapeutics. There’s a bunch here. And we’ll kind of dip into each of these categories at some point.

But my curiosity for you, Brett, you’ve been in a lot of different companies, and so I’m wondering what your methodology looks like when you first come in. What are some of the things you’re looking at to help them grow? I don’t know if you want to take an example, but what do you do first?

Brett Browman 06:09

Yeah. So, you know, the analogy I love to use is like an ER doctor triaging a patient. You know they come in, we have seen countless cases similar to them beforehand. And through pattern recognition and my own experience, you can pretty quickly figure out what the diagnosis is and then what the prescription is like, what the company should be doing. Given that we run the full stage of companies like what that company needs or what their like acute problem is around growth and marketing it is usually very different.

There’s a very early stage like almost seed stage I would call it, I focused on the company that I’m working with now called highlight. That makes a context where I assistant. So it carries context across everything you do on the computer. And then you can interact with the chat bot instead of, you know, going to ChatGPT and sort of pasting these things and explaining to ChatGPT what you’re doing for them. It’s like going to the market.

So how do we scale this thing both organically through paid acquisition like Google ads? How do we hire and help them build a team around this? Like I’m very hands on and in the weeds with this. The thing that I’ve found that is most interesting about this job is how important it is and how difficult it can be to build relationships with the teams in a way that lets you be impactful. You know when you are a consultant, the company is bought into working with you, they’re paying you.

And so they want output and they want to hear your input. You know, technically we sit on most of these companies’ boards and like I could go tattle on them, the company to the investor if they’re not listening to me. But you know that burns bridges and that’s not a way to build relationships. And so I have to come into companies where, you know, the CEO and the founder are exceptionally excited by what we can offer. It’s like, well, you can help grow this thing like that.

Who’s going to turn that down? But the day to day happens usually 1 to 2 levels below that with the actual execution members on the team. And those people are often threatened by me. You know, they see me coming in and like, I’m going to audit what they’re doing and maybe, you know, tattle on them if things aren’t going well. And the reality is sometimes that that is what I’m going to be doing, and building trust in a way that lets me influence them and be a partner with them is like one of the hardest parts of this job.

And I do that through the ethos I have in my head is like no task. I’m above no task, meaning like the most menial of tasks, especially to start like if I need to go into your Google Ads account and like help you set up like some conversion tracking or like some very rudimentary basic thing that I did 15 years ago, starting my career. Like I will absolutely do that. And it is through those, you know, like I am here to support you in any way that I can. And I will show that through action that you can build those relationships with people and over time, influence them and have a real impact on the outcome of the company.

Dr. Jeremy Weisz 09:43

Yeah. I mean, you mentioned a couple key things here, and I think this applies to any leader, right. Especially when someone new comes in, whether it’s internal or external, the guard is going to be up a little bit. Right. It’s just a survival instinct. And so I’m curious how you have learned from a leadership perspective. You know, like gaining the rapport and coming in because like your mentality is there like I’m just here to help. I’m a partner.

But, you know, conveying that in a short period of time when you also want to have impactful results with the team, what do you do from leadership? And, you know, I don’t know what you call it rapport, perspective when you’re going in fresh because every company you go in, it’s a similar scenario.

Brett Browman 10:28

Yeah. So I you know, one of the things that I think great leaders do is they help elevate the people that they lead and help, you know, their talents shine through and help them get recognition and credit for when they do a good job, or when those talents get to shine through. And so a lot of my work, especially with more of the execution focused people that are closer to the work, is empowering them and helping them appear, you know, competent and good to the rest of the company. 

And a lot of the people I work with that they just want to learn like they’re very eager for leadership guidance. And if I can help teach them things and like, teach them how to fish, and then they can show the company and leadership that they know how to fish, because working with me like that engenders a ton of trust. And that’s like one of the things I try to do most is, you know, not not take credit for these things, help elevate the people that I’m working with.

Dr. Jeremy Weisz 11:31

I want to talk about something I know that is near and dear to your heart, which is marketing channels and growth. Okay. Yeah. And we’ll talk about a number of channels. But I do want to start because even when I was doing research, Brett, what I love is you also geek out on direct response and actually direct mail.

Okay. But I want to start going back to square days. Okay. Where you cut your teeth on digital marketing and talk about some of the channels that worked there and, and what you did at Square.

Brett Browman 12:10

Yeah, definitely. So at Square I came in, I joined there when there were about 40 people. We were processing payments like less than $1 million a day. Like it was a very small company, just the white credit card reader that plugs in the phone that was made for, you know, Flora’s dog walkers and that type. And so I was tasked with running all online marketing, and this was.

Dr. Jeremy Weisz 12:37

Just to give people context, but I think Square had I don’t know, you’ve caught me. Do they have over 10,000 staff now or something like that? 

Brett Browman 12:47

Yeah. They’re, they’re, they’re huge. I mean it’s a, it’s.

Dr. Jeremy Weisz 12:50

A you’re within 40 people now. They’re over 10,000.

Brett Browman 12:53

Yeah. I mean it’s a 30 billion I don’t know what the market cap is today, but it’s a it’s a very large public company now with, you know, millions of, of merchants using them for payment processing and then Cash App, also the consumer app, you know, competes with Venmo is is huge too. And that was launched when I was there. But so I came in essentially to run growth. And this was 2011 when like the Facebook ad platform like I remember they had just introduced gender and location targeting.

Like this was like extremely early days of all of these ad platforms that are like household names now. And so I started building those things up and what I found. One of the biggest challenges that I find companies facing that I work with is not understanding their ICP. So their ideal customer profile and like not having a real concrete understanding of who they’re selling to, what differentiates them, why should someone care and what pain points do I solve? And for squares we had such an exceptionally clear understanding of that.

It was, again, you know, the taxi driver, the florist, the dog walker, the trunk show salesmen, the people that were close to commerce and just couldn’t accept credit cards as part of their transacting. They were mostly cash based, but we had a very good understanding of who that customer was. And so then it was just, okay, how do we find the channels where these people are meta at the time or Facebook at the time. Google search, like all of the traditional channels that you would build up, is what we ended up building up, including direct mail as you mentioned. But it started with that understanding of who the customer was and what they cared about.

Dr. Jeremy Weisz 14:48

That is it’s key, especially if you’re going to be spending a lot of money targeting someone. You have to know what you’re targeting. Because I was talking to someone earlier today, Brett, and I was asking, who’s your ideal client? And they were saying, oh, it’s over.

Someone, whatever. Someone who’s over 5 million. I’m like, that’s not really. That’s like one small target, but it’s not like a pain point, right? When you’re talking, it’s someone who takes cash and can’t accept credit.

I mean, there’s certain pain points involved. And so I kind of dug a little bit deeper, but at that point it becomes, you know, obviously obvious that the person doesn’t really know. They haven’t really niched down far enough to see, like, who do they best serve?

Brett Browman 15:30

Totally. totally. And like, you know, there’s a company where everybody knows Quora. They make a chatbot called Po, which is like an aggregator of chatbots like ChatGPT Claude, image models you can interact with through Po. And when I was at Andreessen, I was working with them on growth. And, you know, first question like who is this target at? Like what do we want to acquire here? And the answer was like AI enthusiasts. And it’s like that. 

That is not a category. And that’s not like a customer. That’s not a pain point that people have. And so we had to go many layers deeper into things like students. It was a very big use case for those who wanted to use different models because different models are better at different things like research tasks. graphic designers are one that want to use different image models. So like having to go down like ten layers deeper into like real customer personas with real pain points and then creating campaigns and ads that actually speak to them. That’s what unlocked growth for them when I worked with them.

Dr. Jeremy Weisz 16:34

Yeah. So is that how. I mean, you know, I was going to ask you, like, how do you navigate someone through the net? It sounds like you, you know, basically take who are your best success stories, case studies and really dig into all of the attributes of that persona and then speak directly to that persona.

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