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Working from Home: Week Thirty-Eight

Today marks the end of my thirty-eighth week of working from home (mostly). Here are my takeaways from week thirty-eight:

  • Winter – The temperature in Atlanta dropped quickly this week. It was a reminder that winter is upon us. The cold weather, shorter days, and reduced sunshine will make working from home challenging for me.
  • 2021 – I was asked today what I think next year will look like. I had a few tentative ideas, but the truth is I have no clue. Everyone is planning for a year that is so uncertain. I’m hopeful that things won’t get drastically worse, but I’ll have a plan just in case.
  • More deals – Last week, I reflected on deal and fundraising activity levels. Salesforce’s acquisition of Slack was another huge tech deal. I suspect we’ll see more big deals announced before the end of the year. I’m starting to think about all the variables driving the flurry of deals.

Week thirty-eight was the first week of winter for me. I don’t like cold weather, but I’m starting to adjust to the reality of the next few months. I’m already thinking about spring sunshine.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

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Working from Home: Week Thirty-Seven

Today marks the end of my thirty-seventh week of working from home (mostly). Here are my takeaways from week thirty-seven:

  • Thanksgiving – It was great to have time off. This year has been very unusual and Thanksgiving was no exception.
  • Southeast ecosystem – I connected virtually with a venture capital fund and an accelerator this week. Both conversations were enlightening. I’m surprised there’s so much activity I’m unaware of. All signs are that the region is headed in the right direction.
  • Fundraising activity –There’s been a lot of fundraising activity in Atlanta in the last few months. Before year-end we’ll see a few more deals. Acquisitions, private equity recaps, venture capital fundraising . . . I’m happy for these founders and their teams. We’re in uncertain times, yet investors are bullish on ownership in private tech companies. I’m curious about what the future holds.

Week thirty-seven was low key. The holiday was much needed. I’m glad I got some downtime and could reflect on the things I’m thankful for. Before I know it, Christmas will be here.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

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Working from Home: Week Thirty-Six

Today marked the end of my thirty-sixth week of working from home (mostly). Here are my takeaways from week thirty-six:

  • Thanksgiving rush – Unexpectedly, there was a Thanksgiving rush this week. Many people were trying to meet or wrap things up before next week. Busy, busy, busy! Note to self: plan for it to happen again before Christmas.
  • Giving back – I had an exciting opportunity: participating in a feedback session for a group of early entrepreneurs. This group will do well, and I’m looking forward to keeping in touch and helping them on their journey.
  • Zoom limits – I participated in two Zoom meetings this week that were four and five hours long. And I joined a few others that lasted an hour or more. The longer meetings were helpful for connecting with people and achieving goals, but they were brutal mentally. I can’t do more than one of these long meetings in a week anymore.  

Week thirty-six was busy. I’m glad it’s over and that next week is a holiday week. Some downtime will be good.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

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Technical Teams Outside the United States

As a former nontechnical founder, I understand how hard it is to build a company that relies on technology. One popular route to building technology is to use technical talent based outside the United States. We used a hybrid approach at CCAW comprising both US and non-US technical talent. Here are some of the things I learned:

  • Fit is key – Finding the right person for the role is hard. Spend time making sure the person is a good fit before you pull the trigger. I’ve used Toptal, Upwork, and other services. Regardless of the service, I’ve always had to spend time evaluating the person or firm for fit. It’s one of the most important parts of the process, and you can’t outsource it. Spend time on the front end.
  • Nearshore versus offshore – There’s a difference. Offshore refers to another country that has a different time zone and isn’t close to your country. At CCAW, we had offshore team members in Greece, Poland, and the Philippines. Nearshore usually refers to a country in close proximity with yours and the same (or almost the same) time zone. Nearshore can be easier because it’s more likely they’ll understand your culture and have similar work hours. We had nearshore team members in Nicaragua at CCAW. Both nearshore and offshore worked for us at CCAW.
  • Communication – This is more important than technical abilities. You need to be able to easily communicate with someone. If they can’t communicate clearly in your language, orally or in writing, it will become a huge problem.
  • Individuals versus firms – There is a difference here, too. A good dev shop will have the processes, systems, and management layers in place that will increase the chances of success. We had success working with individuals early on at CCAW. As we began scaling and needed more structure, we had success with firms that already had management structures. I enjoyed have one point of contact to manage the relationship.
  • Product vision – Someone domestic on your team needs to own the vision for the product and they need to work closely with technical talents to make sure their work meets expectations. This may be the founder early on and someone else as the company grows. I originally had this role at CCAW, but transitioned it as we grew. If you can’t articulate what you want built, the end result will be poor, and it won’t be the technical talent’s fault.
  • Expense item versus team member – If technology is key to your strategy, treat the people building it accordingly. Don’t treat them like a line item on the budget. Don’t try to get something for nothing. Don’t just give them a bunch of tasks with no context. Treat them like team members and value the technical insights they bring. Include them in conversations and ask for their perspective. Good technical talents can tell whether you value what they contribute. If you don’t, they’ll decline to work with you and you’ll be left working with people of lesser talent.
  • Expectations – Know what you expect and communicate it clearly from the very beginning.

I learned a great deal working with a hybrid team at CCAW. Our team members based outside the United States were strong, and I’m happy I had the opportunity to work with them. Without these people, we would not have been able to achieve eight figures in revenue.

I know a number of wildly successful founders of technology companies who have loved using non-US technical talent. Conversely, I’ve known others who’ve had bad experiences. I personally think there are amazing technical talents outside the United States and that working with them is a huge opportunity for founders. And I think the founder’s perspective and approach determine the likelihood of success.

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Working from Home: Week Thirty-Five

Today marked the end of my thirty-fifth week of working from home (mostly). Here are my takeaways from week thirty-five:

  • Hybrid college class – This week I presented to an entrepreneurship class at a local university. I attended virtually, but the class was hybrid. Some students were in the classroom (with masks), and others joined in via Zoom. It was interesting to watch. I’m wondering if the hybrid model will be the norm for undergraduate courses.
  • Holidays –I noticed that people are talking about holiday plans and scheduling things is becoming more difficult. I think people are beginning to go into holiday mode mentally. This year has been rough, and I imagine lots of folks are looking forward to the holidays more than ever.
  • Strengthening teams – I’m thinking more about how teams can build bonds and rapport while everyone is working from home. As I wrote yesterday, I think random unplanned conversations strengthen teams way more than people think, and they’re nonexistent now. It feels like the missing link in this work-from-home world. If this problem is solvable, it’s a massive opportunity.

Week thirty-five was pretty calm and uneventful. I guess I’m starting to adjust my pace to holiday mode too!

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

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Working from Home: Week Thirty-Four

Today marked the end of my thirty-fourth week of working from home (mostly). Here are my takeaways from week thirty-four:

  • Election – Keeping up with the election cut into my productivity quite a bit. Looking forward to a decision so we can all move forward. I foresee Atlanta being on more people’s radar because of its outsize influence on this election.  
  • Work-from-home posts These posts began as a way for me to document working from home during a pandemic. They’ve morphed into more of a weekly reflection. I get more out of this habit than I originally envisioned and really enjoy it. My daily posts cover the last 24 hours, but I’ve benefited from reflecting on my week as well. Numbering the weekly reflections has helped me appreciate how much time has passed. I’ll continue doing these posts even when I’m not working from home anymore. Look for them to be renamed in ’21.

Week thirty-four was an interesting one. I’m ready for the election to be over so I can get back to focusing on other things.

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

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Working from Home: Week Thirty-Three

Today marked the end of my thirty-third week of working from home (mostly). Here are my takeaways from week thirty-three:

  • Election – Next week’s election is top of mind for me (and many others. I’m encouraged by the high voter turnout so far. More people are exercising their right to vote, which I love (regardless of their views).
  • October – The month is over tomorrow, and it’s been a whirlwind. I’ve settled more into my second act as an investor and started to get into a groove that works for me. I still need to work on lots of things, but October was better than September.
  • Points of failure – This week, many in Atlanta were without power because of Hurricane Zeta. It disrupted things, for sure. I’m now wondering how working from home and more points of failure at each worker’s home (e.g., power outages and internet connectivity issues) are interacting. Working from home is here to stay in some form, I believe, but large companies will be thinking about helping their teams mitigate these problems as much as possible.

Week thirty-three was a good week and October was a good month. Looking forward to finishing out the rest of the year strong, safe, and healthy!

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

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Rookie Mistakes 101: Waiting Too Long to Transition a Team Member

One of the most difficult things any early founder has to deal with is transitioning a team member. I struggled with it and every founder I know struggled with it at some point. Early teams are close knit and can feel like family. Here are a few things I’ve learned over the years that may be helpful:

  • Everyone knows – When someone isn’t pulling their weight or they’re struggling to keep up, it’s not a secret. Especially on small teams. Most people won’t say anything to the founder, but they’re thinking about it. A players want to work with A players. A C player can pull down the productivity of the entire team. No one wants to give 100% if they know others give only 70%.
  • Company needs evolve – Companies go through growth stages just like people. What’s needed to be successful changes with each stage. Someone’s skills may be great at stage one but insufficient at stage two. It’s common for people to outgrow a company, and vice versa.
  • Trust your gut – With every person I’ve transitioned, I knew long before the day came that it would need to be done. Most founders say the same thing. I often waited quite a while to make the change, which was a mistake. It wasn’t good for the person or the company. It’s better to rip the bandage off and allow people to find a role (internally or externally) that sets them up for success than to allow them to continually fail.
  • One step ahead – Founders are captains of a ship. They should be looking far out and adjusting course to reach the destination while avoiding icebergs that might sink it. Staying a step ahead can give your people the opportunity to grow their skill set before they’re needed (if you tell them what skills they need to work on). Or it will give you time to find someone with the right skills for the role.

What I’ve said doesn’t apply just to non-founders, but to founders as well. Companies can outgrow the skills of their founder. Founders need to be self-aware and constantly working to make sure their skills match the company’s needs. When people see founders working to make themselves better, they tend to want to do the same.

People are critical to the success of any company and you should always treat everyone fairly and with dignity. Early founders need to realize that keeping someone on too long can harm them, not help them. It’s terrible for their confidence to continually fail. Transitioning them to a role they’re better suited for may be painful in the short term but it will set them and the company up for long-term success.

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Working from Home: Week Thirty-Two

Friday marked the end of my thirty-second week of working from home (mostly). Here are my takeaways from week thirty-two:

  • Pitch events – This week was busy because of events. Techstars, Venture Atlanta, and others gave companies opportunities to pitch to investors and the community. I wasn’t able to attend everything, but I enjoyed what I did make it to. These events are a great opportunity for entrepreneurs to introduce their companies to a wide variety of people. Lots of companies present when they’re raising capital.
  • Outlander event – Our team is working hard to bring interesting events to the Southeast. We have some great stuff in the pipeline. I’m excited about our pitch competition for female founders. Can’t wait to see what problems they’re solving.
  • Progress – I couldn’t make progress on everything on my list this week. I guess that was to be expected because of all the events. I’m looking forward to getting back on track next week. I’m going to try Jean-Michel Lemieux’s “1, 3, and 5” approach.
  • Relationships – Relationships came to the fore this week. I helped a few connections with projects they’re working on, and others did the same for me. Healthy relationships are bidirectional, and I enjoy helping others however I can. It’s great to see someone become successful and know you played a small role in helping them get there.

Week thirty-two was full of events. I’m looking forward to putting my head down and focusing next week. My goal is to wrap up a few big things before the holiday.  

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

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Virtual Learning: Venture Atlanta

Today I attended Venture Atlanta. It’s the first year they’ve done a virtual event, but I was impressed. One of the conversations I enjoyed was with Jean-Michel Lemieux, CTO at Shopify and former VP of engineering at Atlassian. Shopify’s platform has made it easier than ever for small and medium-sized business to have an e‑commerce presence. It’s grown tremendously during the pandemic as traditional businesses look for ways to sell online quickly. Jean-Michel shared a few great things:

  • Shopify’s leaders realized they couldn’t recruit the talent they needed in Ottawa, Ontario, from tech havens like San Francisco. They opted to hire young and focus on developing talent quickly. They’ve been intentional about connecting their junior team members with more experienced people in the local community from large tech companies like Blackberry and Nortel. And they’ve gone as far as hiring full-time coaches to ensure that the team has the support it needs to develop quickly.
  • Jean-Michel begins his week by figuring out what his “1, 3, and 5” are. What’s the one thing that has to get done this week? He won’t leave the office until it’s been completed. What are the three things he should be able to get done? What are the five things it would be nice to get done? If the top thing gets done and some of the should-get-done ones are addressed, it was a good week. Anything more is a bonus.
  • He allows zero meetings on Wednesday so he can have an entire day to focus.
  • Figure out what’s unique about your location or city. When you know, leverage it. Lean into it. Don’t try to be like other cities. Create your own identity by playing to your strengths, not comparing yourself to others.

Jean-Michel has hit the start-up lottery twice by working in senior roles at two of the larger publicly traded tech companies outside of Silicon Valley. He shared a ton of nuggets, and it’s clear from today’s conversation that he’s a talented person. I’m a fan of Shopify and will be excited to see how it continues to help small and medium-sized businesses thrive digitally!

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