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The Art of the Hustle
What I've learned from starting a Fractional & Advisory practice
Note from Deb: I have recently gotten a lot of questions about what a career outside a startup or corporate environment can look like. With recent layoffs and Covid changing how work and life integrate, many experienced leaders are considering fractional, consulting, and advisory services. This path is growing in popularity as flexibility—both corporate and personal—becomes more important during an uncertain time in our industry.
The foremost expert I send people to on this is Ha Nguyen. (You might remember her awesome post on building a personal board of directors.) She started NextStep with her business partner, Garrett Kelly, earlier this year. The interest in her work got so high that I asked her to share her secrets on Perspectives. Even if you are not immediately interested in taking the fractional and advisory path, I believe everyone can learn a thing or two about hustling from someone who is both a rainmaker and an activator.
A fractional leader at a company wears many hats: strategist, operations specialist, business development expert, leadership coach, advisor, and cheerleader. But why would a company decide to bring one on, and what does the job actually involve?
These were just a few of the topics I got to explore in my conversation with Nandita Ghosh, most recently the Director of Growth Marketing at Meta. We discussed my journey from working in product to co-founding a VC firm to founding NextStep, my fractional and advisory practice, and what I’ve learned in the six months since getting started.
Whether you’re thinking of going the fractional route or you’re a founder wondering if you should bring on a fractional executive, this interview is for you! You can read the full transcript below.
Nandita: To start off, what does it mean to be a “fractional executive?”
Ha: NextStep actually has two different models: fractional and advisory. In our fractional practice, we are brought on to temporarily fill a leadership position at a company. So if you’re missing an executive on your team—a COO, VP of Ops, Chief of Staff, Head of Growth, Head of Business Development—we can step in and fill this missing role. We’re embedded in the team, we have deliverables, and we’re actually rolling up our sleeves and doing the work.
The advisory part of our practice is less hands-on. We don’t own deliverables, but we support strategy, provide advice, and coach the CEOs or their teams around how to drive to better outcomes. There are also other things we do that add a ton of value to our founders, like network introductions and reviewing fundraising and strategy decks.
Nandita: Are these fractional roles typically long-term commitments?
Ha: Founders who haven’t worked with a fractional executive before usually want to start with a short-term or month-to-month engagement. But if you deliver real value, they want to keep working with you. We haven’t lost a client yet. After just a few months, my business partner and I are at this incredibly privileged point in the journey where we’re telling founders, “We don’t have the capacity. We’ll let you know when we free up.”
Once you’re in the business, working directly with founders and helping them drive business outcomes, they just don’t want to let you go. Even if it’s project-focused, they always find other things to pull you into if you are adding value.
Nandita: So how did you go from working in Product to the VC space to getting into this fractional executive role? What’s your story?
Ha: In the late 90s, I saw the dot com boom happening, and that was when I realized I needed to get out to Silicon Valley. I was lucky enough to join eBay, which was still an early-stage startup, as one of the first six PMs they brought on. After five years, I realized I wanted to go back to an early-stage company because I enjoyed the “building” phase more than the “scaling” phase. I ended up joining four different VC-backed startups as the VP of Product.
After sixteen years, I wanted to explore new opportunities, so I took some time off. While I was on sabbatical, I reconnected with my old boss from my eBay days, Shripriya Mahesh, who was now a Partner at Omidyar Network. She brought me on as an EIR to work with Omidyar’s portfolio companies and coach them on Product. Six months in, I became an Operating Partner, and eventually Shripriya and I formed a new venture firm, Spero Ventures. I was part of the wonderful world of venture for almost five years, and I loved it.
During the fall of 2020, at the height of the pandemic, the founders of Swimply (“the Airbnb of swimming pools”) pitched to me after a summer of pandemic-fueled hyper-growth. While Spero VC didn’t end up investing, I really loved the Swimply story, so I stayed in touch with the founders, who invited me to come help them build the company. I ended up as Swimply’s Chief Experiences Officer, where I ran all of their operations: customer experience, trust and safety, supply growth and optimization, and HR/people. I was responsible for building the company’s early culture and putting in place the operating system for the business.
After two years working 70 to 90 hours a week, I realized it was time to leave Swimply to take a mental health break. I knew I wasn’t ready to return to VC, and I didn’t want to join any more early-stage companies because of how crazy they can get. After Swimply, I knew I could really lead any function—I could do anything, but I didn’t want to join anything. What I enjoy the most is helping early-stage founders build awesome companies. That was when I decided I was ready to build a fractional and advisory practice to help founders become master operators, company builders, and people leaders.
Nandita: Thinking about your own go-to-market for NextStep, are you mostly tapping into your network? Do you have any advice on how you build those relationships?
Ha: My first piece of advice is to put yourself out there. I’ve been in Silicon Valley for over two decades as an operator, and I built a lot of founder and investor connections when I was a VC, but just having a network isn’t everything. You have to make yourself known. When I was on sabbatical, I basically told everyone I met with what I was thinking of doing next, and my network started to make introductions. “Oh, I might know a founder who might need your help.”
There are many ways you can connect with prospective clients. Take my first three clients as an example: one was through a network introduction—just telling my VC friend that I planned on doing startup consulting—and he introduced me to a founder in his portfolio. Another one I met at one of Deb’s events. After the event, the founder and I met up for coffee, and he concluded by saying, “I want us to work together.” The third one was a local marketplace founder who reached out to me over LinkedIn after getting my name from a friend, who told him I was an expert in building local marketplaces. You never know how you’ll meet the founders you’ll end up working with in this business, so it’s important to nurture your relationships.
My second piece of advice is to not underestimate the power of thought leadership. Garrett does a lot of writing, and a lot of founders have reached out to us after reading and resonating with the ideas in his blog posts.
The bottom line is you really don’t know where clients are going to come from. This business requires hustle and a willingness to open the door to new opportunities.
Nandita: What is your ideal customer profile? How does someone who wants to consider fractional or advisory services think about their sweet spot and target audience?
Ha: The work that I love doing, and where I’ve spent so much of my career, is early-stage company building. It may not be so obvious, but at the early stage, it is absolutely about strategy. You have to know not only what your vision is, but what the path is to get there. Where are you going to prioritize your scarce resources? What are the milestones in order to reach the next fundraising round?
Once you start hiring more employees, around the 30 employee mark, everything starts breaking unless you have a really good operating cadence and operating system for the business. That includes goal-setting, performance management, and performance tracking. Garrett and I do a lot of strategy and business operations work.
In the early stages, the focus is also very much on growth, including go-to-market and business development, so we help there as well. I’ve owned growth at a couple different companies, and I can also help founders with fundraising. Where we really stand apart is that we can roll up our sleeves and do the work to help founders build awesome companies. So for us, we decided our focus was to support early-stage founders (seed through Series B). That is where our impact can be greatest and where many startups struggle most.
My advice for those looking to get into Fractional consulting work is to focus on the stage of the company where you have the most experience. Are you an early-stage builder or late-stage scale executive? Focus on where you are most passionate about spending your time and where you think you can uniquely add value.
Nandita: Speaking of rolling up your sleeves, I’d like to talk about this fractional work a bit more. When you’re filling the position of an executive who’s missing, you are expected to function like a full-time employee, but I imagine you lack access to a lot of the “water cooler conversations” you would have if you were fully embedded. How do you gain respect and have impact when your role is expected to be ephemeral?
Ha: It’s important to define the scope of the engagement up front. For example, X hours a week to own Y deliverables and drive to Z outcomes. But you’re right—you can’t be in all the meetings. My advice is, whatever you commit to, commit to it, and do it really well. You don’t need to be in all the team meetings to drive to those outcomes. Join the ones that you think are relevant and will help you do your job better. If you’re missing context, just get it. In my case, I do have access to the board decks, and I have weekly one-on-ones with my CEOs, so if there’s anything I’m missing, I’ll get the information I need or work with them to remove any blockers.
My attitude has always been that you can’t expect things to be easy or that people will give you credibility by default. You have to earn it.
Nandita: You offer executive advisory and consulting services. How do you come into a company with the mantle of support to play that role? How can you ensure that you are successful in each engagement?
Ha: When you start your own thing, you brand yourself however you want to be branded. You have to define, “What is the product or service that I’m offering?” And that’s so somebody can easily reference it and understand how you can support them. But then when you get in, you basically have to roll up your sleeves and help founders or CEOs solve problems. You should know what you’re uniquely good at, and hopefully, you can market and sell what you’re uniquely good at. Then when you come in the door, you have to be good. You just have to deliver, and you’ll be fine.
Nandita: How do you decide what to charge? How do you keep from selling yourself short?
Ha: We work on a cash retainer basis. I actually don’t believe in charging hourly. I believe in a relentless focus on achieving outcomes, however long it takes, and that model does not lend itself to tracking hours. For one client, I initially promised 25 to 40 hours a week, but I have been known to work many more hours than that to achieve the outcomes that we agreed upon. Sometimes by building out scalable processes and systems for my work, I can achieve the outcomes in fewer hours. I don’t want negative incentives in place to take longer to achieve the work because I’ll make more money. At the same time, I don’t want founders to wonder if they should invite me to a meeting if I’m charging them by the hour. With a retainer, founders know how much they should be budgeting for our work, and that our incentives are aligned around delivering outcomes (not hours).
Before I started, other advisors I asked were a bit hesitant to share their engagement rates. I believe in full transparency, and I share my prices openly with everyone who asks. Our minimum monthly advisory retainer is $5k. Our monthly fractional retainer is $10k to $30k, depending on the engagement scope and expected outcomes. We may also ask for equity depending on the achievement of milestones (e.g., closing of a funding round).
One piece of good advice I received early on was to keep my rates high and not sell myself short. I think that was very good advice. I have been building and advising startups for over two decades, and I know that I am very good at what I do. My business partner and I charge reasonable rates for the value we deliver, but we’re not going to be the cheapest option out there. Our founders are very happy with the outcomes we’ve achieved for them because we are pricing on value, not time.
Nandita: How do you scale this business?
Ha: The best way I’ve found to scale myself in this business was finding the right business partner, Garrett Kelly. I recruited him during my sabbatical. He worked for me at Swimply. He was also early at AirBnB, where he ran a 500-person ops team. When I decided on this path, I knew that I wanted to bring Garrett on as my business partner, since we’re both mission-driven and values-aligned. I also knew that consulting can be lonely, so I wanted someone to talk to about ideas that pop into my mind or articles I’m reading.
Garrett and I have complementary skill sets. I’m really good at business development, go-to-market, fundraising, and strategy. He’s really good at business operations and strategy, and he has excellent wisdom and communication skills. So our fractional work often plays to our superpowers. In our typical advisory engagements, I’ll engage with the CEO and participate in some of the strategy and team leadership calls. Garrett generally takes on a lot more of the heavy lifting, such as coaching the team, pulling together frameworks or templates, or setting up their operating systems.
Nandita: What are your favorite and least favorite parts about being a fractional executive?
Ha: I love business development because I’m good at relationship-building and talking to founders. Business development is usually what makes people nervous about going the consulting or advisory route. But my advice to anybody who might be hesitant about that is not to think of it as business development. Think of it as relationship-building. You’ll be meeting awesome founders who are creating the future, working on solving the world’s toughest problems.
There are some things that I don’t like doing, and that’s why I have a business partner. The stuff that he does, especially around operational excellence and business operations—Garrett’s much better at it than I am. I focus on the areas that play to my superpowers and that I think I’m uniquely good at. We’ll play to our strengths, not just on client work but also to build the NextStep practice as well. I’m a natural at building relationships and business development. Garrett’s a master at communications. He will write many of our proposals and close deals. He also built our website, focuses on our thought leadership content, and manages our back-office needs. I found someone who is my ideal complement, and I consider myself incredibly fortunate to have a thought partner in this business.
Nandita: If you could leave one piece of advice for someone thinking about doing an advisory or fractional role, what would it be?
Ha: You’re not selling anything; you’re adding value. It is a privilege to set your own terms. It’s fun to help founders bring their vision to life, but you have to hustle and put yourself out there, or you won’t succeed. Believe in yourself and make things happen.
Ha Nguyen is a Managing Partner of NextStep Advisory and Consulting. She and her partner Garrett Kelly have over three decades of experience building and investing in fast-growth venture backed startups. They’re now combining their knowledge and expertise to support the next generation of early stage founders, helping them take the NextStep to becoming master operators, company builders, and people leaders. If you’re a founder or executive struggling to set strategy, hit targets, or align your teams around performance and outcomes, please email us at firstname.lastname@example.org or email@example.com
We’d love to talk with you about some of the challenges you and your teams are facing and see how we can help!