3 mistakes I made in 2023 and 2 things I got right
As a founder, the only easy day was yesterday.
2023 has been quite a ride.
At the start of the year, if you’d told me I’d be sitting in Palo Alto with family writing this post in December, I’d have dismissed you as clinically insane, unrealistic, or both.
My children have just joined their cohorts in school right after Thanksgiving break, entering mid-way through Elementary and Middle school here.
My wife is supporting everyone in this transition and has been a pillar of strength for the family while also working on a career transition of her own.
All because of a massive bet that we’re making for EngageRocket in entering the largest SaaS market in the world.
Not all has gone swimmingly in this transition of course. I promised that this was a build-in-public blog, so here are some of the learnings - both good and bad - that I’ve reflected on as we enter the last month of the year.
Mistake 1: Exploring the US market alone
This is one I feel the dumbest about.
As a company, we settled on the US as a vital expansion market late in 2022.
So my co-founder and I split our attention between continuing to grow our home market in Asia and figuring out a foothold in the US market.
Whether to conserve money or keep the rest of the team’s attention focused, or both, I felt that until we have more traction I shouldn’t pull anyone with me yet on the long 16-hour commute between Singapore and San Francisco.
That was a stupid mistake.
What this meant was that the only person in the company who had first-hand visibility of the opportunity in the US was me.
Everyone else had to take it as an article of faith. Which rightly wavered depending on the minutiae of our market development efforts month-on-month.
This put everyone in the company, not least my own co-founder, in a difficult position. Take my word at face value as a co-founder, or behold the variable evidence that reflected the trials and errors of our US efforts.
Even if everyone went out on a limb for me, how long could I expect them to do that?
Product decisions: to build for a hypothetically large market with heavy product experimentation and development, or plug feature gaps in our existing pipeline in Asia where we have built up a strong brand over 7 years of operations?
Marketing decisions: to invest limited resources in pulling in top-of-funnel leads from the large US market, or go heavy on localized middle and bottom-of-funnel efforts to support the sales team in Asia?
Sales enablement collateral: concentrate on targeting a limited competitor base in Asia, or focus on specific differentiators against a broad spectrum of competitors in the US?
The list goes on.
Speaking to Sri, the CEO of Rocketlane and 2nd-time founder, as part of this blog made me instantly see how I could’ve done things better.
He routinely took several senior members of his team into the US before expanding from India.
This allowed for a deeper appreciation of the market opportunity, and better problem-solving ability in how to balance resources between the new and home territories.
And ultimately, a more aligned and focused use of resources in tackling prioritization decisions that would surely arise, rather than a split focus that drains resources on both sides without making meaningful progress in either.
Mistake 2: Rushing with “happy ears” in new product development
One thing I love about product development is that it is equal part science and art.
The thing I hate about product development is that it is equal part science and art.
We spent the early part of 2023 developing a product called PerformAI.
This stemmed from a good idea, where even before ChatGPT emerged, we whipped up a simple prototype on Google Sheets in one afternoon and found that leaders, HR professionals and managers were excited by the use of generative AI in crafting, storing and summarizing performance feedback.
When ChatGPT took the world by storm, I felt the FOMO to speed up our development and get something into market quickly, before our competitors would inevitably come across the same idea.
The problem statement was hastily cemented without deeply understanding the exact job that needed to be done, who felt most responsible for the job, and the consequences of getting that job done instead by the next best alternative solution.
I fell in love with the solution, and found myself selling its benefits in customer validation conversations rather than listening for exactly where there was a strong pull from the market.
In a misguided attempt to validate this commercially, I put sales collateral together and attempted to sell the product before understanding why the world needed it.
My own enthusiasm for the project resulted in a team of almost 10 working on it from conception: this introduced too many coordination overheads and encouraged consensus rather than speed. Worse, it made it harder to express contrary interpretations of the feedback data we got, leading to the whole team having “happy ears” from every customer interaction.
Delivery slowed to a crawl. People agonized over button placement and user flows instead of the problem-solution fit. User feedback didn’t flow quickly enough to the whole team because of peripheral busy-ness caused by coordination.
We eventually had to pause development of the product to direct engineering to more urgent projects. And while there are still a lot of useful pieces from the product, and it is still a useful product in itself, it is far from the commercial success that everyone hoped it would be.
That is a painful pill to swallow, but one that I’m learning from and using the lessons to redirect our product and engineering efforts better in 2024.
Mistake 3: All-or-nothing approach to the Ansoff Matrix
The third big mistake I made was believing that we had to live in just one quadrant of the Ansoff Matrix.
This blog has covered the main challenges in operating in what is sometimes known sensationally as the “suicide quadrant”: working a new product in a new market.
The problem is that when expanding into a new market, you do have to make resource trade-offs with your home market. But these aren’t all-or-nothing decisions.
We aren’t forced to operate only in Quadrant 4, even when we find that our existing product takes some tweaking to translate into a new market.
We can still invest in quadrants 2 and 3, while making smaller but strategic bets in quadrant 4.
Recently, I’ve found a better way to think about investing resources through a portfolio approach.
Taking inspiration from Typeform (courtesy of Reforge artefacts…such a great resource), we can now think of our product and GTM efforts using a feature development overlay onto a modified Ansoff Matrix:
This way, we can allocate resources to each of the quadrants and rebalance accordingly throughout the year.
What I got right
✅ Content-led GTM
I spent one full quarter throwing everything and the kitchen sink at the market.
The idea was to quickly learn what stuck, and what didn’t, so that future GTM experimentation can be focused on optimizing channels that work, vs testing those that don’t.
2 different highly-rated omni-channel SDR agencies.
Google, Facebook and Instagram ads.
Cold LinkedIn outreach.
Anything related to cold outreach received dismal results. We were seeing 80% no-show rates on meetings booked by the SDR agencies, and 0.45% positive response rate on outbound email.
That meant that out of 200 people who opened our emails, only 1 would agree to try and set up a meeting.
With a decent open rate (~45%), that still meant that to get 1 positive response, we had to reach out to almost 450 contacts in our ICP.
At a no-show rate of 80%, to get a single productive conversation meant contacting 2,250 people.
I suspected as much, but I confirmed that reaching out to people asking them to buy (or even try!) our stuff just doesn’t work.
The only thing that worked was offering value first.
Generate useful, well-researched, and relevant content specific to our niche. (A recent example would be an upcoming report on the outlook for HR in 2024)
Share that content and get feedback from our ICP.
What resonates?
What doesn’t?
What would make this even more useful?
Then rinse and repeat.
If the content is useful, we can then engage some of our ICP to work with us to co-create the next piece.
This has been the vast majority of our GTM activity that our VP of Growth and I have spent our time on in the past quarter.
The richness of our conversations and the market understanding that comes with it has so far been unparalleled.
It has also been a softer way of introducing what we do to the market, and allow sales to happen more organically, in a way that is actually beneficial to our customers and can add real value, as opposed to a spam-the-world approach.
Win-win-win.
✅ Setting personal boundaries
The other significant win has been finally learning to set boundaries in my day to accomplish what needs to be done.
Juggling all the US time zones while traveling back and forth between SFO and Singapore over 12 months wrecked my circadian rhythm and most of my personal life.
While in Singapore I’d work Eastern time hours to 11-11.30pm, set an alarm for 3.45am or 4.15am to take calls on Pacific time, work with the team in Singapore most of the morning, try to nap in the afternoon but feel guilty and log back on to unblock other areas where I’ve been falling behind at work.
When in the Bay Area, I’d be up from 6.30am taking calls with the East Coast, work through the day, then wrap up at 11-11.30pm with the final calls with Singapore.
And these were on the days where I was disciplined about keeping a schedule.
Initially I told myself that I’d just do it for a few months while I assess the market.
Then it became clear to me that instead of doing it all, I was half-assing my way through and failing at everything.
I wasn’t having enough quality conversations to understand the US buyer.
I wasn’t able to stay close to product discovery and delivery to ensure our investment in our team was well-targeted.
And worst of all, everything had to be so finely balanced on a knife-edge that the slightest derailer meant a bad decision somewhere that required a lot of cleanup, or a missed opportunity that wouldn’t resurface for months, or a wrong word somewhere that damaged a relationship I valued.
I felt I was already working at 120%, and still feeling like I was scraping through at 30% on all counts.
Listening to the Tim Ferriss and Andrew Huberman podcasts on my commutes, I came across Peter Attia’s book Outlive. As part of the well-timed publicity blitz, my co-founder Dorothy recommended it to me also, and I thought I had to read it.
The most valuable thing it did for me was to remind me of what was most important, and to fix those first.
Making space in the day to exercise (getting my heart rate up to ~70% of VO2 Max, or “Zone 2”, interspersed with high intensity workouts and strength resistance training), to meditate during Quiet Time, and to be present with my family, had to be prioritized. The remaining time budget would then be split amongst the most important things that needed to be done at work.
This got me back to designing my ideal week. We’re all only given 168 hours per week. How we decide to spend those hours determines how successful we ultimately are at the things we choose to focus on.
Total contact time at work went down. Yes. But I built pipeline conversations 4X faster and was able to be a lot sharper about understanding the key levers for success in our expansion.
Critically, I mostly managed to not lose my shit during stressful and critical periods of transition and change - in difficult situations with all the people that matter the most to me.
I’m definitely still far from perfect, in many ways. But given how much worse things could have been, I count this semblance of control I have brought back to my life as an important win.
So that’s a retro of my year, and some major lessons I have learnt.
Let me know if any of this resonates with you, I’d love to hear how you’ve solved any of this. I’m also going through a personal and team planning process for 2024, ping me if that’s of interest to put a post together!
This Substack is where I write about our experience expanding from a stable, growing market in Asia, to competing in the largest SaaS market in the world.
We’d like to invite you to join us on this adventure by subscribing:
Thanks for reading Silicon Jungle Chronicles! Subscribe for free to receive new posts and support our journey.
What to expect?
📊 Comparative Data Analysis: Deep dives into metrics and strategies, comparing and contrasting SaaS practices between East and West.
🎙 Podcasts: Candid chats with industry leaders, unveiling the challenges and triumphs of the startup journey.
🎤 Exclusive Interviews: Conversations with SaaS pioneers and innovators, sharing their unique insights and visions.
✍️ Opinion Pieces: My take on trends, disruptions, and the future of tech in these dynamic regions.
Who's this for?
• Founders seeking strategies and stories from dual perspectives.
• Investors eager for a fresh, grounded take on the evolving SaaS landscape.
• Tech enthusiasts, analysts, or anyone curious about the heartbeat of startup ecosystems in both the East and West.
Thanks for reading and do share with someone you think could benefit from it!