The Pursuit of Scrappiness

Rando Rannus is a general partner at Siena Secondary Fund, the first and only dedicated secondary VC fund in the Baltics. With a unique background as both a company founder and operator—having built and sold an advertising business to MTG Group, and held leadership roles at Bolt and Viveo Health—Rando brings an operator’s mindset to venture investing. His fund specializes in providing liquidity to founders, employees, and early investors in high-growth scaleups, with a focus on the CEE and Nordic markets. Through Siena, Rando is pioneering a more flexible, founder-friendly approach to secondaries in a region where the concept is only now beginning to gain momentum.On this episode we talk about:Why over 70% of tech exits in 2024 involved secondary deals and what’s driving this shift in the startup funding lifecycle.How Sienna’s model works, what types of companies qualify, and the benefits for founders and employees.Insight into how deals are valued, including discounting vs. premium pricing, share classes, and rights analysis.Why getting into companies like Bolt and Aura requires trust, timing, and strategic positioning.Rando’s personal story of transitioning from building startups to launching a fund and the lessons learned along the way.==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

Welcome to a new type of episode of the Pursuit of Scrappiness podcast. A monthly analysis of topics we find relevant to highlight, discuss and share with you to help you become a scrappier and better version of yourself. We will be looking at events and developments in business, politics and technology from a European and particularly Baltic perspective.  On this episode we talk about:Baltic funding newsEnefit Green going privateHow Europe strikes back in space and rocket techHarry Stebbings’ new VC initiativeTrade wars & AI wars1/3 Baltics' Biggest Fundraising Announcements  Walk15 secures €5M Series A at a €13M valuation, nearing 1 million users with its activity app.  Change Ventures invests €250K in Latvian energy startup EngyCell, leveraging old Tesla batteries for storage solutions.  Frankenberg Technologies raises €4M for defense tech, including mini-missiles to be tested in Ukraine.Estonian fintech Cino lands €3.5M seed funding for its card-linking payment-splitting app.  Lithuanian startup Commody raises €0.5M pre-seed for NFT-enabled collectible car ownership. Eesti Energia’s €1B buyout of Enefit Green shakes up the Baltic stock exchange.2/3 Europe Strikes Back: Tech Scene Highlights  Harry Stebbings’ 20VC launches a €10M fund targeting founders under 25, backed by top European tech names.  Revolut’s valuation soars to $48B after a Schroder’s stake revaluation, a 1000x return from its 2016 crowdfunding.Bolt acquires Danish taxi startup Vigo to enter Denmark’s regulated ride-hailing market. Secondaries dominate 2024 exits (71%), offering liquidity to startup stakeholders.  EU set to fine Apple and Meta under the Digital Markets Act for competition and privacy violations.  German startup ISAR Aerospace tests a rocket in Norway, aiming to rival SpaceX with NATO backing.3/3 Global & U.S. Highlights  Alibaba invests $50B in an AI model for devices like iPhones and BMWs, intensifying the global AI race.  U.S. job-switching yields only a 4.8% wage increase vs. 4.6% for stayers, signaling a shift in career strategies.  OpenAI’s $40B SoftBank investment hinges on its for-profit transition, challenged by Elon Musk’s lawsuit.  XAI acquires X (Twitter) for $33B, integrating AI with social media amid a $80B valuation for XAI.  DOGE claims $130B in savings, dwarfed by a $500B rise in U.S. government spending, raising questions about impact.==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

Ada Mockutė Jaime, Chief Marketing Officer at Nordcurrent, leads a successful Lithuanian game studio with over 800 million downloads. She shares insights on scaling a business without external funding, emphasizing adaptability and long-term thinking. The discussion touches on the intricate processes of launching mobile games, utilizing TikTok for virality, and the balance of in-app purchases and ad revenue. Ada also critiques gamification strategies in non-gaming businesses, advocating for genuine engagement and the importance of A/B testing in achieving success.

This is an insight from our previous conversation on jumpstarting your tech career by joining Startschool:Apply by March 31st, 2025Get world class training for freeProject based, peer-to-peer learningLearn both tech and business skillsAnna Andersone and Kristofs Blaus are co-founders of StartSchool, a brand new transformative IT and business education program in Latvia, aimed at nurturing future technology leaders. With a unique curriculum combining comprehensive coding education from Silicon Valley and practical startup skills, the program is designed to produce well-rounded graduates ready to launch their own startups or join tech companies. Listen to the full conversation with Anna and Kristofs here on Episode 162:Link to SpotifyLink to Apple Podcastshttps://www.pursuitofscrappiness.co/episodes/162-start-school==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

Marija Rucevska is the founding partner of Outlast Fund, a newly launched venture capital firm focused on early-stage investments in the Baltics and Nordics. With over a decade of experience in the startup ecosystem, Marija has played a key role in shaping the regional tech landscape, contributing with brands like TechChill, Practica, Helve, Techhub and others. On this episode we talk about:The Rise of Early-Stage VC in the Baltics Outlast Fund’s Investment PhilosophyThe Future of Fundraising in the RegionBuilding High-Growth Startups in a Competitive LandscapeDefense Tech and Its Investment Potential==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

This is an insight from our previous conversation on starting a new company as a second-time founder:The mindset of a repeat founder differs substantially from first-time founder - more ambitionApply a structured approach to figuring out your next businessHaving the right founder is still the main key to successDon’t be afraid to start in an unknown industry - there are hidden benefits to thatExecution beats planningMartins Lasmanis is the co-founder of Supliful - a platform that allows you to start your vitamin and supplement dropshipping business in minutes. He is a serial entrepreneur having co-founded and exited companies before. Martins also spent almost 10 years as a VC having seen the business also from the investor side.Listen to the full conversation with Martins here on Episode 138:Link to SpotifyLink to Apple Podcastshttps://www.pursuitofscrappiness.co/episodes/138-martins-lasmanis==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

Welcome to a new type of episode of the Pursuit of Scrappiness podcast. A monthly discussion format on topics we find relevant to highlight, discuss and share with you to help you become a scrappier and better version of yourself. We will be looking at events and developments in business, politics and technology from a European and particularly Baltic perspective. On this episode we talk about:A deep dive into whether Europe’s free speech restrictions are justified, how Germany polices online content, and whether the Baltics have more freedom in comparison.Examining Elon Musk’s Department of Government Efficiency (Doge), its actual impact on U.S. spending, and whether such an initiative would work in Europe.Why Estonia is introducing a 2% defense tax, how it compares to other European countries, and whether other nations should follow suit.A look at the latest investment rounds, including the biggest raises in Estonia, Latvia, and Lithuania, and why growth-stage funding is still lagging behind.A discussion on the crisis in venture capital, why many 2020–2021 funds are still stuck at 1x valuation, and what this means for future startup investments.Are recent tech layoffs driven by AI automation, or is AI just a convenient scapegoat? Analyzing the Klarna and Stripe cases, plus how startups can use AI to stay competitive.==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

Peter Garraghan is the CEO and co-founder of Mindgard, a cybersecurity startup focused on protecting businesses from AI-driven threats. With a background as a professor of computer science and an internationally recognized expert in security, Peter has dedicated his career to understanding and mitigating risks associated with AI systems. Having raised over $8 million in funding, he leads efforts in tackling emerging AI vulnerabilities, ensuring that companies can integrate AI safely into their operations. Featured in Forbes and with over 60 published scientific papers, Peter is at the forefront of AI security research, helping businesses navigate the complex and evolving landscape of artificial intelligence risks.On this episode we talk about:Understanding the vulnerabilities of AI models and why businesses need to take them seriously.The rise of AI-powered scams, phishing attacks, and deepfakes, and how they impact businesses and individuals.Traditional cybersecurity methods vs. the unique challenges posed by AI-driven threats.Best practices for companies integrating AI into their operations without exposing themselves to risks.Where AI security is headed and the potential dangers as AI systems become more autonomous.==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

This is an insight from our previous conversation on building a multi billion dollar company and growth strategy:Companies cannot rely on just one big bet or hope to stumble upon successive growth loops. A long term structured growth plan is requiredThe 70-20-10 Framework for Company Strategy ensures a balance between stability, expansion, and innovation.Investors look for a clear and sustainable plan for growth, not just user acquisition or high valuations.Anastasija Oleinika is the President and Head of Platform of the newly merged Latvian print on demand powerhouse Fyul (Printify + Printful). At the time of recording Anastasija was the CEO of Printify, a platform revolutionizing the print-on-demand market that raised more than 50mUSD in VC funding. Her leadership journey includes her previous CEO role at the Twino investment platform, where similarly to Printify she transitioned from CFO to CEO role.Listen to the full conversation with Anastasija here on Episode 157:Link to SpotifyLink to Apple Podcastshttps://www.pursuitofscrappiness.co/episodes/157-anastasija-oleinika==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show

Artur Schaback is the co-founder of Paxful, a peer-to-peer Bitcoin marketplace and one of the most well-known brands in the crypto industry. Having built Paxful into a major force in the crypto industry, Artur has witnessed the ups and downs of the Bitcoin ecosystem firsthand. He recently left his full-time role at Paxful and is now working on Clip Finance, a DeFi yield optimization protocol, where he is a core contributor.On this episode we talk about:The rise of Paxful and the early days of Bitcoin Growth hacking strategies that scaled Paxful Managing compliance and getting charged by DOJLessons from crypto’s boom and bust cyclesThe role of Decentralized Finance (DeFi) and Clip FinanceTrump’s return and the future of crypto regulations==If you liked this episode or simply want to support the work we do, buy us a coffee or two, or a hundred, with just a few clicks at: https://buymeacoffee.com/pursuitofscrappinessFind all episodes on >  https://www.pursuitofscrappiness.co/Watch select full-length episodes on our YouTube channel > https://www.youtube.com/channel/UCP6ueaLnjS-CQfrMCm2EoTAConnect with us on Linkedin > https://www.linkedin.com/company/pursuit-of-scrappiness/===============Support the show